Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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🗽🗽Attn all (aspiring) personal brand builders in NYC!

I’m hosting an IN PERSON event on Wed Jul 22 to help you become Niche Famous - build a brand that’s seen by the right people to grow your career, network and business!

This post is sponsored by Relay, a business banking platform. Relay is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC.

When I posted my first Instagram video in October 2024, I never thought it could become a business that makes multiple six figures a year. It felt like a fun creative outlet, and “content creator” didn’t sound serious enough to be a real career.

My first brand deal came in January 2025 and it shifted my mental calculus. I made $5,000 from posting a single video.

For most of 2025, I made anywhere from $5,000 to $10,000 a month. It still felt like fun money. A nice bonus on top of my 9-5, not a business.

The end of 2025 felt like a turning point. My brand had grown, and a few things hit at once: tech layoffs, AI slop taking over every feed, and brands that suddenly wanted real storytelling from real people. The creator economy was growing fast, and creator-led businesses were becoming a serious path. Going into 2026, I decided to treat this like a real professional asset instead of a side project.

A big part of “taking it seriously” was the financial side. Even though I started my career in finance and knew the importance of finances, it took me a long time to get around to organizing mine because it felt like boring admin that took me away from growing my business.

But “boring admin” is what turns a side hustle into a business. “Boring admin” saved me money and helped me make more.

I’m not a small business finance expert by any means, but here are the five financial moves I wish I’d made sooner, and what I wish someone had laid out cleanly for me when I started.

1. Form your business entity (usually an LLC)

Before you can do almost anything else on this list, you need an actual business entity. For most creators that means an LLC. It gives you liability protection and lets your business income pass through to you without a separate corporate tax.

I did it after realizing I should separate my business income for taxes (which I needed an LLC for), but wish I knew a few things earlier:

• You don’t need to set up an LLC on day one of posting content or starting a business. You can run a side hustle as a sole proprietor for a while before it’s worth the cost and paperwork. Form it once your income is consistent, not the first week you post, consult or advise.

• In New York, there’s a publication requirement. Within 120 days of forming, you have to publish a notice in two newspapers the county picks for you, for six consecutive weeks, and it runs from a few hundred dollars upstate to well over $1,000 in the city, plus a $50 filing fee (NY Department of State).

• After you form an LLC, you can turn it into an S corp to save on taxes (in most cases). S corp is not a separate entity, it’s a tax election you make on your LLC that starts to make sense once your net income is consistently above roughly $80,000, because you can pay yourself a reasonable salary and take the rest as distributions that skip self-employment tax (it’s location dependent; in some cities like NYC, S corp doesn’t save you as much).

Further reading:

• SBA — Choose a business structure and IRS — Business structures

• U.S. Chamber of Commerce — S Corp vs. LLC

2. Separate your business and personal bank accounts

I ran everything through my personal bank account for way too long. Brand deal payments, my expenses, my rent, my groceries, all in the same place. I couldn’t tell you which part of the business was profitable or how much I’d actually made versus spent.

I put this off because setting up a business banking account meant paperwork and sitting in a branch. I switched to Relay recently and wish I’d known about it earlier, because I set up my account in about five minutes from my couch.

Once the money was separated, everything got easier. I could see what was coming in, make decisions, and pay people cleanly.

Relay also makes it easy to set up separate accounts for different parts of the business, which used to be a hassle. You can also give logins to your accountant, a contractor, or an assistant without sharing your own password, which is huge once you start delegating.

3. Set aside money for taxes every quarter

When you’re running a side hustle next to a 9-5, you have a hundred things going on, and this is the one that’s easiest to ignore. I’d seen other people say to set money aside for taxes. I knew I “should” do this. But I figured I wouldn’t make enough in my first year for it to matter.

Then Q4 2025 happened and I made a lot more than I expected, all at once. Come tax time I had to pull out a huge chunk I hadn’t planned for. It would have been so much less painful if I’d been setting money aside quarterly the whole time.

Now I do this with my accountant every quarter. It’s a hassle, and it saves you from a five or even six-figure tax bill you didn’t see coming. The moment a payment comes in, a set percentage goes into a separate account I don’t touch, so it’s already there when taxes are due.

Further reading: IRS — Estimated taxes.

4. Open a self-employed retirement account

A perk of having self-employment income, if you’re not fully self employed, is that you can open a retirement account built for business owners, on top of any 401(k) you already have at a day job. The two main options are a Solo 401(k) and a SEP IRA, and once my income was consistent, my accountant walked me through both.

The difference (do your own research or talk to your own accountant before acting on this!):

• A SEP IRA makes sense if you want simple. It’s employer contributions only, up to 25% of your net self-employment income, no employee piece, minimal admin.

• A Solo 401(k) lets you save more, especially if your business income is still modest. You contribute as both the “employee” (a flat amount up to $24,500 in 2026) and the “employer” (up to 25%). Because the employee piece is a fixed dollar amount and not a percentage, you can shelter a bigger share of a smaller income than a SEP IRA’s 25%-only cap allows. It also has a Roth option.

The part I missed at first: you can fund one of these on top of a 401(k) at your day job. A SEP IRA is fully separate from that plan, so there’s no overlap to worry about. A Solo 401(k) is trickier, because the “employee” contribution limit ($24,500 in 2026) is a per-person cap shared across all your 401(k)s. Whatever you defer into your day-job plan reduces what you can add as the employee of your own, but your “employer” contribution to your own business 401(k) is separate.

One rule of thumb my accountant shared: your day-job match is free money, so contribute enough there to get the full match, then figure out how to load up on your own plan.

If this is confusing, which one you pick matters less than starting. Starting early beats optimizing later.

Further reading: IRS — Retirement plans for self-employed people.

5. Get a business credit card

3 reasons to get a business credit card:

1. It builds credit for your business. A business card reports to the business credit bureaus under your EIN, separate from your personal credit. Build that history for six months to a year and you can qualify for financing to invest in the business without leaning on your personal score. This matters more as your business grows. I’ve been talking to creators who started YouTube channels, launched podcasts, or moved into in-person events, and all of it needs money upfront: videographers, studio space, gear.

2. It protects you from fraud. If a charge is fraudulent, it’s easier to dispute it and get the money back on a credit card.

3. Points. Not the main reason, but you’re spending on the business anyway, so you may as well earn rewards while you do it.

Relay offers a business credit card too, so you can set it up alongside your accounts: The Relay Visa® Credit Card is issued by Thread Bank, Member FDIC, pursuant to a license from Visa U.S.A. Inc.

Further reading:

• Experian — how to establish and build business credit

• NerdWallet — best business credit cards

• Forbes Advisor - Top business credit cards

When I started my LLC, I kept wishing someone would lay all of this out for me in one place as a creator entrepreneur and 5-9 business owner. Nobody did, so I figured it out one piece at a time, and each thing I set up made the business feel more real and me (a little) less anxious about running it.

So don’t try to do everything this week. Start with getting an LLC and separating your business finances.

Thank you to Relay for sponsoring this newsletter!

I got to have dinner with their team in person last month and sat down with their CEO Yoseph West (made him take a pic!) to hear about everything they’re building for solopreneurs and small business owners. It feels like a platform that’s going to keep evolving with me as my business grows, so I’m excited to introduce you to it!

💵 Sign up for Relay 💵

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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The first time I came across Mishti Sharma was from her LinkedIn post earlier this year, where she told the story of how she landed the storytelling job that tech companies were “desperately seeking”:

I instantly stalked her LinkedIn, and realized her career was anything but linear. She studied philosophy at Princeton, worked in finance, joined startups, went self-employed, and somehow ended up leading storytelling at Clay. At the same time, she was writing maildrop by mishti about diaspora stories and getting published in the New York Times.

My conversation with Mishti was a treat because of the range we were able to cover, given how much she’s done in her career, and I’m so excited to share this one with you. We covered:

• making two “low status” career moves in a row, and why you can’t plan your career

• what storytelling actually is and how to do it

• how to become a better writer, and how (not) to use AI

• the value of a personal brand and how to build one

• what a GTM engineer is and who makes a great one

Princeton philosophy to endowment fund

Hannah: Take us back to the start. What were you like in college, what did you want to do, and how did you end up at the Princeton Endowment Fund?

Mishti: I loved college so much. I loved all of school. I majored in philosophy, partly because I was interested in it as a subject, but also because it was the most flexible major and had the least requirements. I’ve always had a strong independent streak. I wanted to take whatever classes I wanted and not be constrained by some department requirement. So I constructed my own experience. I took everything from ancient Greek and Sanskrit to classes that took me to Brazil to study contemporary art and Mexico to study Mayan hieroglyphics. My thesis even combined STEM, psychology, philosophy, and politics.

I loved college so I extended the ride. I did a Fulbright in India the year after I graduated, which was also very self-directed and an amazing life experience. I was trying to postpone coming into the real world for as long as possible, because I had this view that, “Alright, I’ve got to earn some money,” and pretty much the only routes are law or finance for what I’d studied. I had a job offer from the endowment fund, but I applied to the Rhodes and the Gates. I was basically asking, “what can I possibly do to not take this job?” I almost got some of the fellowships, but none quite worked out.

Hannah: But you ended up taking the endowment fund job eventually?

Mishti: I ended up moving back to Princeton. I remember having a huge argument with my parents, because I said, “What if I just moved to Spain and learned Spanish for a year?” And they said, “Are you out of your mind? You have to get a job.” So that’s how I ended up at the endowment fund.

I had a great mentor I’m still in touch with, but as a whole, it was the absolute worst personality fit I could have had with a job. We did a personality test called the Predictive Index.,The whole office had to take it. I remember them, graphing people’s extraversion, formality, and other factors and showing our aggregate results on a screen. I was all the way over on one end of the graph and everyone else was on the other end. It was a very corporate and hierarchical place. “Don’t leave your desk until your manager has left or it’ll look bad” energy. We had these huge sprints every quarter before board meetings where we did insane amounts of what often felt like busy work, but we took it so seriously. It is a great opportunity for some people, but it was just a complete mismatch for me and I wasn’t happy.

Why you can’t plan a career ten steps ahead (and what to do instead)

Hannah: Was there any upside to your finance role?

Mishti: The one upside was that the endowment fund invested in a lot of venture capital funds, which gave me exposure to the startup world from the investor side. I got to travel to India, China, and Silicon Valley to meet VCs, and they’d often bring founders from their portfolio companies into meetings. Watching them, I realized, that’s what I want to be closer to. I’d actually tried starting a company in college, so that pull had always been there. Working at the endowment fund just made it impossible to ignore. That’s what led me to create my own first startup role in 2020, right as COVID was starting.

It was a product growth role—basically me and the founder and a bunch of engineers. I was in Figma designing screens and thinking about UX a lot, and it was a consumer social startup, very different from Clay, which is B2B. We were constantly building and tearing down, seeing if we could build apps or web experiences people would enjoy. During COVID, we started by hosting virtual conversations with authors before eventually exploring a bunch of different product ideas. It ended up being product, growth, community, or whatever needed doing. I was showrunning and hosting shows.

Hannah: Something you’ve said about pivots stuck with me, that you can’t really plan that many steps in advance.

Mishti: Someone in college asked me how to think about career trajectory, what to do when. And I said you can’t really think that many steps in advance. I did one thing, I really liked it. I did the next thing, it was absolutely awful. And when I’m there I think to myself, “okay, not that, but I’m closer.” You’re making little adjustments, and it ends up putting you in the right place eventually.

Hannah: That’s hard to take in the moment, though. How were you okay with it in real time?

Mishti: Definitely hard. I had a really hard time leaving the endowment fund, because my parents said, don’t quit until you’ve found another job. So it was a grind. Every waking moment I wasn’t working, I was talking to founders. I’d spend my lunch breaks on calls and write one-pagers every evening. That felt like a bigger shift because I was exiting the industry entirely.

After that, it’s been adjustments within the startup world, because that has its own status hierarchies. You work at a startup, then you’re supposed to be a founder, the whole tech Twitter status ladder. Or at a startup as a generalist, you should do product, that’s the sexiest thing unless you’re technical. But those felt like much smaller adjustments once I’d found the kind of work that actually fit me.

Building the connections that got her into rooms like Clay

Hannah: You knew Varun for a while before Clay, through a friend. So much of early-stage startups is about the people, not the product, since the product is going to pivot. How do you build those connections, and read that energy from the outside?

Mishti: It started with me wanting to make my first pivot out of finance. I made a list of everyone who was a relevant college alum, all the VC funds I thought were cool, and asked, do I know anyone there. From Princeton, because we’d invested in some funds, I had a few routes in. I looked at portfolio companies at those VCs, saw which ones seemed interesting, and asked, “could I find a connection?” It was a giant mapping exercise. That’s actually how I met Varun. A friend introduced us after I asked who she thought I should know. That was probably the most proactive I’ve ever been, because making that career change felt existentially important.

I still do this. On LinkedIn or Twitter, if I see someone really interesting or like-minded, I’ll reach out. I’ve made a lot of internet friends, more on Twitter before the Elon acquisition, who I’m still in touch with. Sometimes years later, someone you reached out to online might end up working with you. It happens a lot. It’s about being open to finding kindred spirits and reaching out to them.

Making peace with two “low-status” moves simultaneously

Hannah: In your First Round piece you wrote that you made two low-status moves at the same time: joining a cold-email startup and taking a content role there. Coming from the same world, I know how unsexy content reads to finance people. How did you become okay with that?

Mishti: I think people are most worried about that kind of thing when you don’t really trust or know your company that well. If Clay had been the median company, the kind that doesn’t value this role, doesn’t pay it well, doesn’t have career progression for it, then I’d think: why wouldn’t I do my own writing projects on the side, and at work, just play the game really well? I know I can play any game well, I’ve studied all sorts of things. Why wouldn’t I optimize for that and save my soul for myself? But that comes from a lack of trust and knowledge about what the company would value. And it would probably have been a correct assumption at a lot of companies.

What made me comfortable was the proof from the founders, and as Clay grew, the validation that this was one of the most important things you could be doing at the company. People respected it. I wasn’t setting myself back. Money talks, the fact that I was paid well and got a good equity grant made me feel a lot better, because the role felt respected and valued.

Why the same work can be “low status” in one room and “high status” in another

Hannah: So you essentially have to find a place where what the outside world sees as low status is treated as high status.

Mishti: A friend of mine tweeted that some people spend their lives chasing what’s high status, and some people have the conviction that they’re just going to do whatever they’re amazing at, and that it will become high status.

It’s both. It’s being in the right environment where I’ll be valued for this. And then you see it play out. Now everyone in the industry is reaching out asking, how do you do your narrative and storytelling, how can I build teams like this, how can I hire people like this. No one knows what amazing work in a so-far-ignored discipline looks like until someone actually does it for the first time. That applies to any function: community, partnerships, whatever. When you push the boundaries, the industry notices eventually. But being able to push the boundaries of a function assumes you’re in the right container to do it.

Hannah: It’s wild how relative status is depending on the room you’re in.

Mishti: It’s very weird. The endowment thought highly of themselves; they had $36 billion, they were funding these VCs. The VCs would be catering to the us, trying to get our investments—but if you talk to VCs, many of them don’t really respect their LPs that much, or at least consider most LPs to be that smart. The same thing happens between VCs and founders. And if you talk to founders, they often don’t consider most VCs to be that smart. Everyone thinks they’re the one doing the right thing, and it comes with this derisive approach to things outside your bubble. I don’t know why we feel the need to do that as humans, but there’s a lot of it.

What storytelling jobs actually are (and how to get one)

Hannah: Storytelling is having a moment, but how do you actually define the job? Every founder, every PMM, every operator wants to do it, and these narrative and brand lead jobs keep popping up that people say Netflix is paying $775K for, but no one quite knows if it’s comms, content, or something else.

Mishti: I can define what I do now, and it’s different as an IC versus leading a team. After PMM I went back to being an IC and did a lot of foundational narrative work, though we weren’t really calling it that, I was just an IC in marketing. Then we said, okay, this is worth building a team around. So we started the narrative team, which blended social, influencer, all editorial (video and text), and creators. Everything that’s a creative storytelling function, all in one. Notion has done this too.

Our job was mostly responsible for how the world understands Clay and the industry we’re in. PMM, for us, is Clay the product. Narrative is responsible for how people see Clay the company, and whether we’re creating something like GTM engineering as a whole new industry and career, powering the growth of how the function evolves.

Hannah: And now that you’re back to being an IC?

Mishti: About six months in, I realized I was more interested in being a creator myself, learning to do that really well, telling these stories, doing my own one-shot projects. It’s a critical team, and as the company grows, leading it gets super operational. So now my job splits in two. I still lead our messaging on every major announcement, the most fundamental moments for the company: fundraise announcements, a big product moment, a manifesto, GTM engineering expanding into a new region. And the other half is being an in-house creator for Clay, focused a lot on YouTube right now. We just launched a channel for business explainers and journalism about interesting companies and really niche jobs. I source and create those stories. The bet is that if they do well, it’s worth Clay’s investment in me, because once a video blows up it’s an evergreen lead magnet. Clay is such a horizontal platform that we can tie almost any story back to something we do, and if not, it’s brand awareness.

Hannah: This is such an emerging role. For someone who wants it now, how do they even get the job?

Mishti: A couple of things help. One is having a public body of work, ideally writing, or at least including writing. There’s maybe a separate, more video-focused track, so you could combine both, but have at least one strong body of work that shows quality. It doesn’t have to be about startups. If it’s really good, people trust you can write. If it’s about startups, even better.

Beyond that, my general advice on creating jobs: most companies don’t have storytelling strength and want it, especially now. Really learn about a company and reach out. Say, I saw this is what you do, I imagine you’re trying to reach this kind of person, here’s what’s falling short on your website, or, I tried your product and here was my experience, your case studies read like this. Do an audit, give them free advice, and make it good. If you have both of those, there’s no way you don’t get a job.

If someone reached out to me right now and said, Clay has a huge newsletter opportunity, you started a Substack but you’re not active on it, here’s the kind of stuff I’d write, and here’s my writing, what if I just did a newsletter for you? We’d hire them in one second. It’s simple but hard. You almost need years of work to get to the point where you can do it, but it’s possible

How to become a better writer (and how to use AI)

Hannah: To do storytelling you have to be good at writing. Have you always been? Is it a natural thing or a buildable skill?

Mishti: I think I’ve always been good at writing, it’s been my thing as early as I can remember. It ties back to reading a huge amount as a kid. Always maxing out the library, reading at my desk, reading with a flashlight in bed. I’ve kept a meticulous Goodreads since middle school, and it basically averages out to a book a week for my entire life. I was always interested in writing, I just never thought it would be lucrative. I wanted to be an author. I admire people like Jhumpa Lahiri and Joan Didion, diaspora writers and essayists, and I was modeling my path against theirs. So the convergence has been really cool.

I think studying philosophy helped a lot too. You don’t have to study philosophy, but people still don’t register in their souls how critical it is to be able to form a logical argument well and tell it cleanly. Even if you can’t write to make me feel emotion, can you at least construct an argument coherently?

Hannah: You mentioned you use AI a lot. How, exactly?

Mishti: I do, a lot. That First Round piece, I used AI so much, but in a very different way than people assume. I’d say, give me seven different transition sentences from this paragraph to the next, because it doesn’t flow. Or, this logically doesn’t flow, how do we rearrange the ideas? It’s very much how I imagine engineers use AI to code. You have the logic and the vision, and you test different ways and pick what gets you in the right direction. I’ll also write something messy and say, give me ten ways of saying this sentiment, because if you don’t start with anything, it won’t give you anything good.

Hannah: So can writing be learned?

Mishti: I think and hope so. The number one thing is read good stuff. If you don’t think you’re a good writer, read ten times more high-quality things than you do now. When I’m trying to write a short story, I’ll read a short story first to get in the zone. It sounds simple, but that’s where I’d start. People could also learn a lot about argument construction. Argument mapping is an exercise we did in college, and it’s amazing how many people think they have an argument when it’s just an opinion with no logical coherence.

Hannah: Banking helped me here, oddly. Building a PowerPoint slide, thinking about what the header is and what supports it, is a different side of the same skill.

Mishti: Exactly. And it’s important to have people with high standards pushing back on you, who won’t let you put random stuff on a slide. Writing is iterative too. Only about 1% of editors give me good feedback on the bones of an argument. Most say, oh, this is great, great vibes, you’re a great writer. You need someone who goes seven layers below and says, you said this earlier but you’re not backing it up in the middle of the piece.

What a GTM engineer actually does and who’s good at it

Hannah: So many new roles are being invented right now at startups where you don’t need the perfect background. Storytelling is one. The GTM engineer is another, and Clay really created that role. How do you define it, and who’s good at it?

Mishti: Go-to-market engineering is the practice of removing every obstacle to a company’s growth. Any process that’s too manual, too slow, too broken, a GTM engineer should be able to go in and use technology, AI, and systems thinking to automate it away or make it much more efficient.

On who’s good at it: on our own team we have a variety of backgrounds. You don’t need a coding background at all, you can teach yourself anything right now with how good AI is. But you need the curiosity and the ability to break down business problems, plus you’ll either have or learn low-code automation or vibe coding really well. That’s the magic combination. On our team we have a former designer, former software engineers, people from RevOps who did traditional RevOps without AI and shifted into this, people from sales. Now they all heavily use Clay, Claude Code, lots of tools. GTM engineers can be T-shaped. One person’s job is, make our reps 100 times more productive, go sit with them, figure out what’s broken, and solve it. Someone else sits with marketing and figures out how to make event invites, follow-ups, and lifecycle emails more efficient. It’s like data science, you can embed them into different functions. The general skill set is automation and vibe coding plus business fundamentals.

How to build a personal brand that builds you optionality

Hannah: You’ve done a lot to shape Clay’s narrative, which supports your personal brand, and you also have your newsletter and post on LinkedIn. How do you think about your own brand versus Clay’s?

Mishti: I’ve been having the most fun at work now that I’ve realized they can actually converge. Clay and I both get a lot out of what I’m doing. After Clay, which I have no timeline on, but if and when I leave, I’d love the freedom to have a couple of high-value consulting contracts in my sweet spot that fund other things I want to do. Or maybe I’m a creator full-time and that pays my bills and more. It comes from knowing myself. I don’t think I’m that interested in working for another company again, and I don’t want to build a giant company. I want to earn a lot of money powered by just myself.

I posted about this on LinkedIn, but I’ve met people who just give LinkedIn posting advice, not even ghostwriters, charging clients 50K a month. There are so many ways to make money that come from being yourself visibly and authentically online, attracting the right people, and using that. People have already reached out wanting to hire me or asking if I’d do consulting, and I haven’t really done anything yet.

It builds optionality. Even if you never leave your company, it gives you power and a sense of agency, knowing you could do anything. So whatever you’re doing in the moment is really what you’re choosing to do.

The best metric for brand-building: “Did the right people see this?”

Hannah: What’s your best advice for someone building a brand or doing storytelling, whether for their business or for themselves?

Mishti: For both, but especially personal brand, it comes down to authenticity. People know when you’re being real. You can be real about being a hustler salesperson and it’ll work, or real about finding a nonlinear career, or finding your place with storytelling. Whatever it is, lean into what you’re uniquely excellent at and share it publicly.

The other thing, for personal and company both: early on, your success metric isn’t whether you get a thousand followers, or X many likes. It’s, “did the right people see this and reach back out to me?”, even if it’s one or two people. That will always lead you in the right direction.

There’s a Henrik Karlsson blog post about how blog posts are beacons, they say “here’s who I am, let the world see this and the right people will come find me”. Treating it like that is more rewarding and more mentally healthy, because you’re not trying to max out your metrics. You’re there for the right people to meet you. It’s a very human practice at the end of the day.

Connect with Mishti on LinkedIn, read maildrop by mishti on Substack, and check out her First Round essay on betting on Clay.

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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Substack in 2026 is like TikTok in 2019.

20K on Substack feels like 200K on Instagram.

The platform crossed 5 million paid subscriptions last year, up 67% year over year. When TikTok was stuck in its US legal limbo, Substack put up a $20M fund just to poach creators off it. Even Charli XCX started a Substack last November and pulled in around 12,000 subscribers in a single day.

The money from just “writing words” adds up. More than 50 writers now make over $1M a year from paid subscriptions alone. A New York Magazine salary survey this March found an anonymous fashion Substacker making $275,000 a year, most of it from brand partnerships, vs. a NY Times bestselling author in the same survey made only $49,000. Emily Sundberg’s Feed Me has 150,000+ readers and the New York Times estimated she pulls in over $400,000 a year from subscriptions (when she only had 60,000 readers), before any brand money.

In an AI world, Substack feels like the analog of digital.

We’re a couple years into the AI slop flood, so the internet is full of generated content that all sound the same. People are tired of short-form content on top of that, to the point that “brain rot” went from a meme to a term in the Oxford dictionary. The reaction has been a swing back toward analog and in-person. CNN ran a piece this January on people “committing to the analog lifestyle” out of AI fatigue, film photography is in a full revival, and run clubs and dinner clubs are more popular than ever.

Substack feels digital but analog: a real person’s voice, long-form, an audience you own (for the most part, and for now) instead of rent from an algorithm. In a feed full of AI slop, a human writing like a human is what stands out. It feels like blogging in the 2010s, except with built-in distribution and less cringey photos.

Substack offers something for everyone. On one end you have Lenny’s Newsletter, a product management and tech focused audience, over a million subscribers and more than $1M a year. On the other you have Maybe Baby and Morning Person, much more personal and culture focused. There’s room for almost anything in between.

The startup cost is one of the lowest of any platform (you don’t have to film or edit), and it’s not LinkedIn, where every professional contact you’ve ever had is watching you post.

So…is it still a good time to start as a new creator? Back in mid-2025, Chenell Basilio, who writes a newsletter about newsletters, predicted that Substack had “12 to 18 months of good opportunity before it gets as crowded as everywhere else.” A year on, that window is still open but closing. The readers are coming in, but the money side only just turned on: Substack just launched early access to Creator Kits a few weeks ago, where creators can build a profile for brand partners to shop from. I got early access as a Substack Bestseller.

Yes, it’s still early. But also…don’t obsess about being early. Just start. I got on Instagram and Tiktok in 2024 feeling like I’d already missed the huge growth cycle, and now I’m at 250K+ followers across both platforms. Timing helps, but showing up and not quitting helps more.

My story with Substack

I had a newsletter before this one that was a weekly list of jobs that my assistant helped curate because I wanted an email list but didn’t want to do any work. It drove some growth but no trust, because a jobs list is a utility. Nobody learned anything about me from it.

I started seriously writing around the end of last year. Since then it’s become my favorite creative practice and the most relationship-building thing I do with my audience. Someone has to consciously decide to sit down and read a long thing I wrote. That’s a completely different relationship than someone double-tapping a reel. I’ve also gained over 2,000 subscribers from Substack alone, reached a 5 figure and growing ARR from paid subscriptions, and even had a post get over 1,000 likes that got reposted…by Substack!!

It’s also the channel that gives me the most clarity behind the scenes on the business and brand I’m building, so I’m probably underestimating all the other ripple effects it has on helping me grow.

Today I’m breaking down:

• Who should start a Substack

• What to write about without forcing yourself into a niche

• How to write something people resonate with and recommend

• Substack’s cold start problem and how to build a growth engine that fits you

• The 4 ways to turn good writing into an income stream

Plus my real growth breakdown from the last 90 days, the actual percentages and where every subscriber came from, what I’d copy from it (and what I wouldn’t).

Who should start a Substack

The simple answer first: you should start one if you like to write, or want to become a better writer. If you’d rather make videos, go make videos. A newsletter you don’t enjoy writing becomes drudgery fast.

But let me get more specific, because “do you like to write?” is too broad to be useful. Start a Substack if:

• You were on the school newspaper, or wanted to be.

• You kept a blog that no one read but you still loved writing it.

• You’re an introvert with a lot of thoughts and opinions, and you want a way to put yourself out there that doesn’t involve a camera (at least not at first).

• You actually like to journal.

• You wanted to be Carrie Bradshaw (in the writing-a-column-way, not in the bad relationship decisions way)

• You get a little thrill from writing an exceptionally well-worded email.

• You’re building something and want to share the behind the scenes story of it.

• You want to get better at writing and thinking clearly, which sharpen each other.

• You have tactical, long-form, how-to knowledge that doesn’t fit into shorter formats.

How to start

Read more

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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A few months ago, Danielle Matarasso sent me a cold LinkedIn message. She has the exact kind of nonlinear, portfolio career I love learning about (and we had a mutual friend), so I replied, and here I am interviewing her for my Substack!

Danielle started in Big 4 accounting, went to Booth for her MBA, and spent five years at a mid-sized tech company. Then she spent a stretch exploring ETA and search funds, and now she’s running her own advisory business, building her LinkedIn presence, and writing AI After Carpool, a weekly newsletter that breaks down AI for parents.

As I learned more about Danielle’s career, I realized she’s building a business in one of the “low status, high income” opportunities I’d been talking about on social media, and one my audience keeps asking me about: helping small and medium-sized businesses adopt AI.

Her firm, Numeriq Advisors, does exactly that, with Danielle handling the implementation herself, drawing on everything she ran across functions at that software company. I knew she’d have a lot to share, whether you’re curious about AI advisory, ETA, or building a portfolio career. We talked about:

• Why she walked away from buying a business after looking at 150 deals

• Her honest take on ETA in 2026, and why it now looks more like VC than the old playbook

• How she’d evaluate a deal now, and where AI creates an edge

• What her AI advisory does day to day, and how someone breaks into this work

• The one skill she says matters more than any pedigree

• How she’s building a portfolio career around her family, and what her ambition looks like as a mom

Danielle's wealth of experience across finance, small businesses and tech is apparent in everything we talked about, so I hope you get as much out of today’s newsletter as I did putting it together!

Why she went to business school, and the post-MBA plan that fell apart

Hannah: Why did you go to business school, and what did you set out to do?

Danielle: I came out of undergrad right after 2008. There was all this PTSD over finance, no jobs, so all of us were running to accounting. Accounting in Canada is rigorous. It’s a three-year internship, the exams are all case-based. Accountants there are kind of the business advisors who go on to become the CEOs of companies. It’s a very different profile than in the US.

I did my internship in Montreal and Toronto, and a third of it in Tel Aviv. I quickly pivoted into M&A, doing buy-side and sell-side diligence, because I wanted to get close to deals. I did a lot of software, because that was the scene then, 2014-2016, when SaaS was becoming a thing. I loved it, but I got stuck on the advisor side and thought, maybe I should pivot completely into tech.

My husband and I started our careers together in Canada, and he wanted to apply for MBAs in the US. I’m Canadian, so my rule was: I’m not moving to the US to watch you do an MBA; I’ll only do it if we do it together. We applied to two schools and ended up at Booth. He went down the traditional finance path. I wanted to try everything that wasn’t finance and accounting where I had come from. My goal was to figure out how to break into tech, maybe do product, because that’s what everyone was doing at the time.

Hannah: How did you first get exposed to ETA?

Danielle: It started halfway through my second year at Booth. I came from a family with a third-generation textile business - very boring, typical immigrant family from Europe. They started by selling small pieces of fabric and built it into a real business. The warehouse was dingy and dark, in a part of town that only later got gentrified. That’s what I grew up with, so when people started talking about ETA, I thought, maybe that’s my version of entrepreneurship.

Before that, I was exploring VC-backed startups, I led the startup trek at Booth, and I thought I was going to go into product in Big Tech. But then I realized I don’t want to be a small piece in a huge pie at Amazon, Facebook, or Google. I figured I’d give ETA a try instead.

I was still risk averse, so instead of buying something myself, I took an offer to work as a CXO. That type of program, run by PE firms and search funds, was just starting then. I was set to go to Pacific Lake, one of the top ETA firms in Boston. I’d signed and everything.

And then life got in the way.

I got married right before business school, to my husband who was in school with me. We figured we’d have our first kid right after, before I started the job. Once you start having kids, you realize that’s not how the world works. You can’t plan everything. I ended up six months pregnant when we graduated.

I had to give up the Boston offer because my husband got a job in Chicago at a family office, which is where we wanted to move. So there I was, post-MBA, all my friends going off to amazing jobs, and I’d just given up my dream offer. Six months pregnant, none of my friends pregnant, wondering what the heck I was doing with my life. It felt really hard. I did consulting for a year postpartum, working up until 41 weeks with my own little business and keeping it going after the baby. But I was still itching to be in tech.

Why you should choose a job for the function over the company or industry

Hannah: How did you get back into tech, and how did you choose where to work?

Danielle: I used my Booth network, which is where the MBA truly did help me. I reached out to the VC I interned for during business school, and they put me in touch with their portfolio companies. I almost took a job I really loved in the women’s health space.

But here’s the thing. The women’s health job was in an industry I thought I was passionate about, but the actual function and skills were ones I hated. The other option was a local job in Chicago, in an industry I couldn’t care less about, but the work itself was fascinating. I’d be leading a new sales vertical: figuring out which vertical to go into, owning the strategy, hiring the salespeople, managing BDRs and reps and a quota.

That’s the thing when you’re figuring out where to go. You can love the company and be passionate about it, but if the day-to-day won’t give you the skills you need, or you won’t enjoy it, it’s probably not worth your time. Because the day-to-day is what you’re actually doing. That’s why I chose the role over the industry.

Running five functions in five years, and why you need to own a number

Hannah: You ended up running a lot more than that one vertical.

Danielle: I spent about five years there. I ran the new vertical. Then I took over customer marketing and product marketing. Then product growth, because we were a software business. At some point account management came under my wing. And eventually I became VP of corporate development, which meant I ran all the partnerships across every vertical. That drove 30% of the business or more in a given year.

So I came for tech, got exposed to ETA, thought I was going to do ETA, life happened, and I still ended up back in tech. Just not in a typical product management role at a big company.

Hannah: How did that distinction manifest in your tech careers vs. others?

Danielle: I see a bunch of my friends who’ve gotten laid off in tech over the last couple of years. When you’re at a really big company at a certain level, our level, and you don’t own anything, it’s hard to trust that you could do something different afterward. Owning something is what proves you can.

Rethinking risk aversion when your “why” changes

Hannah: You took the tech job partly because you said you were risk averse. Now you’ve left to build your own thing. Has your risk aversion gone down, or how did you get over it?

Danielle: My perspective has changed. I was risk averse while I was having kids. I know it’s funny to call a VP role at a good company risk averse, but I knew what my body could handle. You can’t work 50, 60, 70 hours when you’re pregnant or trying to have kids. So back then, my risk aversion was really about protecting my body at that stage of life.

Now my why has changed, which changes my risk aversion. My why isn’t to make tons of money. It’s to feel like, when I get to the last decade of my life, I don’t have regrets. Part of that is wanting less. I have this conversation with peers a couple years ahead of me. They’ve already committed to the second home, the really fancy vacations every year, and they don’t want to strip that away. I’ve been intentional since business school that my wins are my kids having a good education, a safe place to live, a good support system. I have that padding built in, so I’m okay forgoing the very high salary right now for a longer-term build, because I believe it’ll pay off.

It’s almost like that ETA book, “How to Buy a Small Business”, where they show you how much you actually make if you get the exit at the end. Your peers might earn a higher salary at the beginning, but by the time you annualize it, once you get your sale, you end up in the same place. The biggest piece, though, is just not wanting too much in the moment. That’s what’s helped me manage my risk aversion.

Her honest take on ETA in 2026: crowded, expensive, and more like VC than it used to be

Hannah: You’ve spent a lot of time looking at ETA, and you’ve written that it’s gotten crowded, the thesis has changed, debt isn’t cheap, multiples are high. What’s your advice for someone in 2026 about to spend a year looking at 150 deals like you did?

Danielle: It’s a different market now than when I looked in 2018, 2019. There are a lot more people in it. Back then, everyone took the ETA class but nobody took action, so when the actual funds came to talk to you, it’d be me and six other guys in the room. Now it’s you and a hundred other people. I went to the ETA conference in November 2025 and it was insanely packed. I went to the same one in Chicago in 2018 and it was nowhere near as full. There was also a lot less diversity in 2018 than now, which is a nice thing to see. There’s a whole community for women searchers that I’m part of, and it’s really flourishing.

There’s also been a lot of false narratives about how easy it is. You’ve got the bootcamps, the Cody Sanchezes of the world, so much content. Which is great, but it downplays how hard it actually is.

Hannah: What’s pushing the multiples up on small businesses?

Danielle: A couple of things. There was a window, roughly 2000 to 2015, where deals really did get done at two to three, three and a half times. If you go back to the Harvard Business Review book, the whole thesis is buying something for two to four and not above. That’s where the math works.

Now it’s a lot easier to find deals. What you can build with Claude, to go find the companies and mass-email them, just wasn’t possible before. So the barrier to entry dropped, and more people came in. And because it’s been so popularized, Wall Street Journal, my dad sending me articles about young people buying up Boomer businesses, you’ve also got the seller mentality, plus more brokers in the space. So it’s harder to get a quality business at those multiples. You can probably still buy turnarounds for less.

Debt was really cheap for a bunch of years, 2014, 2015, 2016, post-recession, so deals were less likely to fail from a debt-servicing perspective. But if you’re paying a much higher multiple and your interest rate is higher, it’s not the same. The profile starts to look more like VC than the traditional ETA search model from the early 2000s. That’s starting to become clearer. But if you go in with eyes wide open, that’s totally fine.

How to evaluate an ETA deal now: compress operating costs, not the deliverable

Hannah: So how should someone evaluate a deal now?

Danielle: I left thinking I could buy any business as long as it was in Chicagoland. Then you start looking at a lot of businesses and your why comes out. Do I really want to own that? You realize it’s not only about the money. Maybe that’s easier for me to say. I’m a few years post-MBA, I’ve had more of a career, I have kids. I don’t have the same energy to hustle the way I did in my late 20s. If you’re younger, no kids, 25, you can hustle. Once you’re 30, the energy starts dropping.

I started thinking about professional services. It could be done remotely, and I understood the clients and the customers. I looked at tons of deals and realized, holy shit, AI is going to change this industry significantly. And the multiples were insane. I looked at deals at six, seven, eight, nine times. That’s not two to four, that’s twice as expensive, and on top of a complete change in how the work gets done.

Hannah: So what’s the lens you’d use now?

Danielle: You should think hard about how AI will compress your operating costs, not your deliverable. What you don’t want is AI making the actual product easier to deliver. If I run an accounting or bookkeeping business and AI can automate the deliverable itself, then at some point that business isn’t relevant anymore.

What I’m looking at now is purely youth enrichment. Dance studios, martial arts. AI isn’t going to replace the teacher in the room. But AI can take a real bite out of the operating costs behind it. I can probably have three or four people do the work that used to take eight, nine, ten, especially if you’re rolling up a lot of locations. So AI reduces your operating costs without touching your product delivery. That’s how I think about an ETA business in 2026.

What Numeriq does, and why she’d rather “teach businesses to fish” than hand them a deck

Hannah: That’s a great segue to Numeriq. You’re doing a lot of the work you would have done in ETA, just in a different way, still focused on small and mid-sized businesses. What does the advisory do, day to day?

Danielle: A few things. Every career skills assessment I’ve ever done, at Booth and through work, always came back the same: I like to learn and I like to teach. Things are changing so quickly that I’m not doing repetitive work. I’m always learning a new way to use a tool. And because I was an operator for so long, I don’t do it like the M&A consulting days, where you hand someone a deck, here’s the value of the company, and walk away. I’m teaching them to fish. They get the tools, they learn how to use them, and they keep running with it.

So it might be setting up Claude for a whole team. I pick a couple of lanes. A big one is the sales process. Another is content and demand gen, taking all the content you have and repurposing it effectively, pre and post events, your podcast, your customer journey. Another is building AI CFOs if you understand the accounting world.

A big part of my job is helping them figure out which workflows cause the most pain, in terms of time, not even money, and where AI truly fits to help them do better.

The most valuable career skill to build: driving revenue

Hannah: What’s the experience you think is most valuable for what you do now, and how do you get it if you haven’t been thrown into a bunch of functions? Your experience running everything at a smaller company, knowing exactly what your customers go through, is what lets you do this now. It goes against the Silicon Valley line that when you get on a rocket ship you don’t ask what seat. The seat matters, because it gives you the skills to leave and build on your own.

Danielle: Anything close to the customer, with a number tied to that customer. Whether that’s a sales number, a marketing number where you’re on the hook for a certain amount of closed-won revenue, or an account management role where you’re responsible for upselling a customer by a certain amount. As long as you’re tied to a revenue number.

I know that sounds obvious. But at the end of the day, a business is a business because you make money, because you have paying customers. You can build whatever you want and think you’re building for the right person, but if you’re not actually selling it to them and seeing the attribution back to customers who spent their money, you’re missing how you learn the most. You can dream up all these wonderful ideas with the engineers, but the person selling it is the one who really understands why it isn’t working, why it isn’t what the customer wants.

Hannah: Why do you think so many smart professionals, especially MBAs, avoid that?

Danielle: A lot of MBAs avoid sales with a ten-foot pole because it’s so freaking hard. The biggest shock in my first role was hiring salespeople and reps and BDRs, and coaching them. Listening to their Gong calls, giving feedback on how they talk, on discovery. You can’t appreciate a sales pipeline review until you’ve owned one. Or you look at marketing and ask, did this event drive leads? If not, was it because I didn’t have a pre and post event process? Did I not figure out the right ICP? Are we marketing to someone adjacent to our ICP instead of the actual buyer? Am I getting to the decision makers? All of that is so important and so hard, which is why MBAs don’t touch it. It feels not intellectual. But it’s the most intellectually challenging thing you can do. So anything that teaches you how to sell, period.

Hannah: At the highest levels of the most coveted post-MBA jobs, finance, consulting, it’s really just sales. Glad you called that out.

Living in two worlds, and refusing to go all in on either

Hannah: You made decisions that optimized for family over career at certain points, while staying a very ambitious person. A lot of ambitious women struggle to reconcile those. How do you think about it?

Danielle: Part of why I launched my Substack is that I was living in two worlds. The parenting world, and my MBA and work-friends world. I was trying to bring them closer together, because there are a lot of women right now who, if they’re not up to speed on how the world is changing, are going to get pulled further and further out. Seeing how much my friends didn’t know is what pushed me to start it. It’s purely for fun right now.

It’s going to forever be an identity crisis, and it’s probably not going away. The only way it goes away is if you live in a world where all your kids’ friends, and their moms, happen to be the same ambitious career women as you, and they probably won’t be. What you have to focus on is being really intentional about spending time in both places. If you don’t spend time in the community where your kids are, that’s not good for them or your family. If you don’t fill your cup with ambitious women, that’s not good for you either.

You’ll forever have two different worlds. You just have to find a way to be okay with that, and make time for both. Don’t neglect one over the other. Don’t go all in on mommy and forget about your brain.

Building a portfolio career on AI advisory, content, and ETA

Hannah: Your Substack, AI After Carpool, shows the different sides of who you are. How are you thinking about your career as a portfolio going forward, and where do content and personal brand fit in?

Danielle: AI After Carpool started as a passion project when a friend asked me, “What’s Claude?” And I thought, oh my God, what is going on. My friends are still using it like it’s a search engine. I have friends in really good corporate jobs, and corporate is actually part of the problem, because they limit what you can use for security reasons, so a lot of people aren’t even dabbling in their personal lives.

So the newsletter fills my creative junkie mind and my teaching itch, and it forces me to think about new ways to use AI in my own life and systems. It feeds from what I’m learning in the consulting work, and what I build there tells me what to share with my audience at a more accessible level, so people can actually start using it.

Hannah: And it brought you back to ETA in a way.

Danielle: Going deep on AI After Carpool, I kept realizing the skills our kids will need in the next 10 or 15 years are very different from the playbook we were given. Be smart, go to school, get good grades, get a good job, save, retire. That’s not a thing anymore. That’s what brought me full circle. If I’m going to do ETA in the future, I want to invest in something I care about that will actually bring value, which is in-person experiences for kids that AI can’t replace. That becomes even more important as we see what social media and screens do.

So it all comes together. The consulting brings in money right now and I’m learning. AI After Carpool lets me share that with my network. And the biggest thing for me is helping my friends understand what’s even possible, for their careers, their creativity, and raising kids in a world that’s shifting. The personal brand piece, I’m just trying it. I’m out of my comfort zone. I’m more of a shy person, I’ve been off social media for a while, I’m improving as a writer. But I’m curious, and curiosity wins.

Follow Danielle on LinkedIn to watch her build in public, and subscribe to her Substack, AI After Carpool, for practical AI tips (especially if you’re a parent).

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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Today’s post is on a topic I've been thinking about a lot because I'm working on a new series on Instagram on building a personal brand in your 5-9 as a knowledge creator (stay tuned!!).

I know a lot of us are probably sick to our stomachs hearing about personal brands…but this is slightly different view I hope you’ll consider xx

And stay tuned - I also have a VERY exciting interview dropping in next week’s issue with someone who will talk more about her nonlinear career and building a personal brand in a very unique way!

My resume is all over the place.

When I was 21, I started my career in equities sales, then moved into real estate banking…both in Hong Kong. Then I left finance for tech (more specifically - at a global ride-hailing company that was launching in Latin America). Then I got an MBA to pivot into product, but ended up doing product marketing at a B2B SaaS company. Now I’m also the founder of a creator business.

If you just looked at that on paper, you’d probably ask the same thing many interviewers did:

“So what do you actually want to do?”

I’ve sat across from people who were visibly confused, trying to work out how any of that added up to the role I was interviewing for.

If that’s you, you know the feeling. You spend the first ten minutes of every conversation justifying your path instead of talking about what value you bring. You sound defensive. And the longer you spend explaining, the more you start to sound like the exact thing you’re afraid of being called: an unreliable job hopper.

There’s a way out of that, and it’s the same solution whether you want a better job or something bigger, like your own business:

You build a personal brand.

My definition of a personal brand (there are many others!) is simply what you’re best known for, which you can eventually build, amplify and monetize into a brand or business based on your expertise and point of view. The latter is often what you see referred to as a “personal brand” more broadly.

There are about as many reasons to build a personal brand as there are definitions. You might want to:

• Land jobs

• Get promoted

• Build an income from sponsorships

• Grow an advisory business

• Network in your industry

• Hire talent

• …

If I were to sum it all up:

A personal brand brings you more opportunities so you can attract, not chase.

And people with nonlinear careers have the most to gain from building one.

When your career path follows a straight line, your title and your resume explain you. You show up in LinkedIns searches for “Product Manager” or whatever job you want because it’s already the title you have. Or you look like a star founder when fundraising because you have years in an industry.

When your career zig zags, you're left to do the explaining yourself, over and over. You don’t show up on recruiters radars because they can’t search for you by title. When you’re starting a new venture you look completely inexperienced in your field or function.A personal brand fixes that.

You craft a clear story that you can get in front of the right people so you skip the explaining and attract opportunities instead.

It’s what got me numerous inbound offers like this one despite having less than 2 years of formal “marketing” experience in my title and a very nonlinear career:

It’s what gets me 90% of my brand deals, with brands like LinkedIn, Notion, and Adobe.

It’s what gets people I admire in my industry (marketing, startups, creator economy) to reach out to me instead of the other way around for networking.

Without a story, you look like a flight risk, and you spend interviews explaining it instead of selling yourself. That’s the visible cost, and it’s the one people focus on. The cost we rarely talk about is what all that explaining does to you on the inside.

Without a brand, you feel like an imposter

A reader put it better than I could:

“I find that most people self-select themselves out of opportunities, especially boxing themselves into what skills they have and don’t. My background is years of consulting, I struggled with burnout and a toxic culture, and I was impacted by a layoff last fall. I’m trying to overcome the rejection from interviewing at multiple high-growth startups, and I’m scared to build and learn in public to build a brand. But I’m also seeing the pattern of others like me afraid of not just the rejection, but the fear of believing you’re worth the opportunity and the skill needed to thrive in a high-growth environment.”

I know this feeling well. When I left banking I was burnt out, and the startup I joined next was intense in a completely different way. While I was job searching, and even after I joined, I feared for a long time that I couldn’t “hack it” in a high-growth environment.

I had invented a story that everyone around me seemed smarter, sharper, better at execution, and I assumed I was the weak link. Because I was the one with the nonlinear path and they had done the job or held the title for longer than I did.

What I eventually figured out is that imposter syndrome starts before day one. It’s not really about whether you can do the job (in most cases, you absolutely can). A lot of it is set in motion before you ever walk in the door.

When you apply for a role you don’t obviously fit, you spend the whole process shaping yourself to it.

You trim your experience to match the job description, downplay the parts that don’t line up, and try to make the square peg fit the round hole. By the time you start, you’ve spent weeks making the case to yourself and others that you sort of belong, so you walk in primed to look for proof that you don’t. That’s where the imposter feeling grows.

A personal brand flips that entirely. When you’ve put out a clear case for what you’re good at, people come to you, and they’re the ones fitting a role to you instead of you contorting to fit theirs. You don’t have to explain yourself, which is the thing that sets off the imposter feeling in the first place, so you start on solid footing.

My friend Yuqi, who I interviewed for this newsletter, is a great example of this. She leads Developer Community with no formal community experience. Instead, she’d built a brand that articulated why her product background and her habit of building community in public made her the right fit. She showed she could do the job before she her first interview and never had to justify her experience against the job description line by line.

And sometimes the role doesn’t even exist until your brand creates it. My friend and mentor Upasna recently joined the American Journalism Project in a Head of Product & AI Studio role at the intersection of journalism, AI, product, and venture. It was created for her, because her brand made it obvious she was the person for a job nobody had even written down the job description for yet.

With a personal brand, opportunities come to you

And it’s the new normal of how hiring will work in the post-AI era, because AI has made it too easy to fake competence.

You can generate a resume, a cover letter, and a portfolio with ChatGPT in 20 minutes. You can use bots to submit hundreds of applications.

Earlier this year, we were hiring for a role at my startup and got flooded with applications. Many were clearly AI-generated. Sifting through resumes where we had no idea if the person actually did the work they claimed was exhausting. Most of the people we interviewed came from referrals, or had worked at a similar company in the same role with experience that was legible and a track record we could verify.

But the person we ended up hiring came in through their personal brand. They’d posted a portfolio publicly, including a teardown of one of our competitors showing how they’d redo the strategy. We reached out, interviewed them, and hired them. They didn’t have the exact title we were hiring for, but they’d already shown they could do the work.

This happened to me too. I got two job offers last year. Both came from startup founders who reached out after seeing my LinkedIn content. Posting publicly helped me rank higher in search, and it gave them a whole body of content that showed what I was capable of before we ever spoke. They could see how I think, how I write, and what I care about. I went into the interviews from a position of strength because they had reached out to me, not the other way around.

And it’s the same content that does double duty. The brand that gets you hired is the same one that attracts clients, an audience, and eventually sponsors if you want to go that way. You build the asset once and it compounds in multiple directions.

How to start building your personal brand (30min version)

No, a personal brand is not built in 30 minutes. Or a day, even.

I’ve been building my personal brand for almost two years, with lots of false starts, and trial and error.

But what you can do in 30 minutes is start nailing down the positioning that serves as the foundation for your personal brand, and map out a few first steps to kickstarting the personal brand engine.

Your positioning is, in a nutshell: Who you are, what you’re great at, and why your path makes sense. Distilled down to 1-2 sentences you can reuse everywhere. (If you happen to be a PM or PMM, this is just product positioning adapted to yourself.)

The template version:

FOR [target audience/employer/investors], I AM A [how you describe yourself] WHO PROVIDES [unique value], UNLIKE [default comparison, competitors] BECAUSE I BRING [unique combination].

My positioning, which I adapt from the template version, after spending time figuring out each [bracket]:

I’m an investment banker turned marketer blending business and creative to help B2B brands and high-achieving professionals turn storytelling into revenue.

It’s the first thing you see on my LinkedIn description and how I connect my experience across marketing, my personal brand, and my past experience in finance, business school and B2B SaaS.

Here are three ideas to write yours for a nonlinear career path, if you’re stuck or the template feels too robotic:

1. Anchor around an industry.

Say you’ve spent years in finance and you want to move into operating. You lead with the industry as the throughline:

“I’ve spent years around top consumer companies and saw how the best ones scale, and now I want to bring that inside one as an operator.”

2. Emphasize your skill stack.

If your value is the combination of things you’ve done, lead with that. Say you’ve worked in finance and then operated at a startup, and you’re going for a VC role:

“I’ve worked in finance and as an operator, and a VC role needs both, understanding the numbers and helping founders actually run the company.”

3. Frame around a core question.

If a single thread of curiosity connects your jobs, name it. Say the same question pulled you from sales to customer success:

“I’ve always been curious how companies solve customer problems. That took me through sales and then customer success, and now I want to keep chasing it as a PM building for the customers I used to sell to.”

Your goal isn’t to pretend your path was linear. It’s to show you’ve thought about it and can say why it makes sense for the role you want. Most people with nonlinear careers waffle there. They either downplay their past experience or try to explain every single job. Neither works. And positioning isn’t fixed - it changes with you.

Pick one framing that connects your dots, iterate until it feels right, and evolve it when it shifts.

Your positioning statement is the foundation, but it does nothing sitting in a Google Doc. Once you have it, there are three ideas to put it to work:

1. Put it where people check you out.

Rewrite your LinkedIn headline and About section so the first thing anyone sees is your positioning, not your current job title. This is the part that made founders find me in search and reach out before I’d applied to anything. Do the same with your bio, your email signature, and how you introduce yourself in a room.

2. Turn it into content.

Your positioning is the source material for everything you post, so you’re never stuck on “what do I even talk about.” You’re just showing the work behind the claim. That can be a competitive teardown (like the one the person I hired did), a breakdown of how you’d solve a problem in your space, or thinking out loud about where your field is going. You don’t need to go viral. A handful of LinkedIn posts (or another platform, depending on your industry or goal) is enough to give someone a reason to reach out.

3. Use it to reach out.

Once you can explain yourself in one line, cold and warm outreach get a lot easier. Message the people doing the work you want to be doing, with a clear ask, and let your positioning and your supporting posts do the vouching for you.

The first time you do all of this it’s slow and it feels cringe. That’s normal. But once your positioning is out in the world and you’re posting against it consistently, it stops being just a line you use in interviews and starts bringing the opportunities to you.

If you want a structured way to do this…

I built a Nonlinear Personal Brand 14-Day Sprint in Notion. Basically…how I’d coach you to do all of this in 2 weeks.

It breaks positioning down element by element so you can actually build yours, then turns it into 14 concrete daily steps, 30 minutes or less each, to refresh your LinkedIn, publish your first posts, and send your first outreach. You come out the other side with the real beginnings of a brand instead of a plan in your head to start one.

• Chief of Staff – Stealth startup w/ Tanmay Tankha (Early Stage, San Francisco)

• General Manager (Stanley) & Chief of Staff – Stan (AI Content, Growth Stage)

• General Purpose Smart Person – Tofu (AI GTM, Early Stage, Toronto/NYC)

• Venture Fellow – ResilienceVC (FinTech VC, Washington DC)

• Founding Marketing Lead & Expansion GM – Marble Health (HealthTech, Growth Stage)

• Chief of Staff (2 roles) – Global media co & AI startup, via Omna Search (NYC)

• Chief of Staff – Navan (Travel & Expense, Late Stage)

• Strategy & Operations Manager – Rula (HealthTech, Growth Stage, Remote)

• Director, Office of the CEO (Founder in Residence) – BillionToOne (Molecular Diagnostics, Public, Menlo Park / Hybrid)

• 📢 Build a Nonlinear Personal Brand in 14 Days

• 🧭 The Exit Plan for ambitious people figuring what’s next

• ✨ career tarot cards

• Find me on: Instagram, Linkedin, Tiktok, Youtube

These are my top posts over the last 6+ months since I started writing every week, sorted by category.

Guides cover frameworks and how-tos across career strategy, personal branding, AI, and startups. Stories are conversations with people who built nonlinear careers, like a former product manager turned developer community lead and creator, to an ex-pro tennis player who built a personal brand on LinkedIn.

If you’re new, start anywhere that catches your eye. If you’ve been here a while, have a look at anything you missed.

See you in two weeks! In a very Chinese time of my life until then 😆

Career Strategy

• The Career Changer's Guide to Job Offer Negotiations

• Why I Went to Business School (and My #1 Takeaway)

• How to Onboard Yourself: Your First 90 Days at a New Job When There's No Playbook

• 11 Career Paths Where High Performers Have an Unfair Advantage

Personal Brand & Content

• How I Grew 70K Followers in 4 Months as a 5-9 Creatorpreneur

• So You Want to Start a Newsletter?

• I Thought Personal Brands Were Dumb Until It Got Me a New Job and a Six-Figure Business

• The 5-9 Creator Guide: How I Grew a 6-Figure Side Hustle in a Year

AI & Future of Work

• Why You Need an AI Second Brain (and How I Built Mine in 45 Minutes)

• Everyone Is Going to Have a Nonlinear Career

• How to Build a Fulfilling Career and Not Get Replaced by AI

Startups & Business

• The Multi-Passionate 5-9 Builder's Guide to Focus

• How to Get a Startup Job in 2025

• 7 Ways to Succeed in Startups (from People Who Actually Did It)

Ambition & Achievement

• What to Do When You're Ambitious but Nothing Excites You

• Why I'm Choosing the Low Status, High Income Path to Wealth

• Escaping the Bermuda Triangle of Talent

• The Maximizer's Dilemma (Why You Should Stop Keeping Your Options Open)

Career Pivot, Founder & Creator Stories

• What They Don't Teach You at Business School (Wharton MBA to creator chat)

• How to Turn Your Passion Into a Profitable Lifestyle Business Without Burning Out

• How a Music Grad Turned a Viral Substack Into an AI Career Platform

• How a Wall Street VP Built a Wellness Business Without Leaving Finance

• How a Microsoft Sr Director Reinvented His Career and Built a Personal Brand Without Ever Leaving His Company

• How to Build a Portfolio Career by Investing in Relationship Currency

• How to Use a Gap Year to Pivot and Rebuild Your Career

• How an Ex Goldman Banker and PE Associate Broke Into Startup Ops

• How an Ex-Pro Tennis Player Pivoted From Banking to Startups with Her Personal Brand

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear route.

🌴🌴 This will be my last post for a few weeks. I’m headed on vacation for two weeks and taking a full break (or at least, trying). I’ll be sharing some of my old posts and guides in the meantime!

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Is it just me, or are a lot of ambitious, accomplished people feeling really stuck right now?

In the past few weeks, not one, or two, but four friends have told me they’re feeling stuck, unsure, or stagnant in their careers and lives, and asked me how to get out of it.

One is a founder who can’t decide whether to pivot her startup or go get a job. One quit an intense finance job for tech and now feels unstimulated outside the high-pressure environment she used to complain about. One is burnt out from years of long hours building other people’s startups and wants to start a lifestyle business of her own. And one knows she needs to leave her job but has no idea what she’d do instead.

Call it a rut, a funk, the messy middle…More and more of my circle in their late 20s and early 30s seem to be going through it, especially the ones who are a year or two post-MBA or a few years into finance, consulting, or tech. They’re often silently wondering what’s next, afraid to admit that their perfect-on-paper careers aren’t perfect in practice, or even a little guilty over their “champagne problems”.

And it goes way beyond my group chat. Social media is full of it. I see TikToks every day of people “starting over at 30” or “I quit [insert name brand company here] and have no idea what’s next.”

It makes complete sense. A lot of us feel unaligned with corporate jobs that turned out to be bullshit work and stakeholder management theater instead of the impactful, exciting roles we were promised as high achievers. Meanwhile, a lot of those paths are falling apart in front of us anyway, between layoffs and salaries don’t move much each year.

How do I figure out what’s next?

My answer to this question was why I started creating content 2 years ago, so it’s one I still get a lot. I’ve written and spoken about my own life after banking, when I felt apathetic about basically everything, and how I slowly clawed my way to figuring out what came next.

And I’ve been back in that place more times than I can count: During my MBA, after I crossed product management off my list and didn’t have a backup plan. In the middle of a job at a mid-sized company that I didn’t love. Late last year, when my content felt stagnant and nothing about it excited me anymore.

It’s a question I’ll probably never get tired of answering, because I’ve been through it in so many forms. I know how hard and how impossible it feels when you’re inside it, and helping someone climb out is one of the most fulfilling things I get to do.

So I wanted to write down what I told my friends over the past few weeks, because I’m sure a lot more of you are feeling the same way.

This is a little different from my usual stuff. I’m a tactical, matter-of-fact, non-woo-woo person, but this one gets a bit woo-woo, because it’s kind of a woo-woo problem to solve.

A couple of notes before we start:

This isn’t a long how-to guide. It’s a loosely sequential mix of principles, mindsets, and a few specific things I’ve actually done that helped. If you want something more structured, I’ll point you to another resource at the end. But in my experience, when you’re in the messy middle, throwing a framework or a worksheet at you right away just adds to your anxiety without helping.

Feeling excited about nothing is a different problem from having too many directions and not knowing which to prioritize. That second one is related, but an easier one to solve, and I wrote a separate guide for it: a pragmatic multi-hyphenate’s guide to focus. My advice below is for when your well of inspiration feels dry.

1. Relax and realize: This is the oldest problem in the world.

Figuring out what’s next is a problem that’s existed for as long as humans have. When you’re in the thick of it, the not-knowing feels like a personal failing, like everyone else got handed a map and you’re the only one wandering around without one. Seeing it as the oldest human problem there is takes a real amount of pressure off.

My founder friend rambling at ChatGPT about which AI app to build is wrestling with the same thing as the hunter-gatherer deciding where the tribe should roam next, or the medieval craftsman paying to have their fortune read. (In a way…)

I was reminded of this recently on a visit to Mass MoCA, the contemporary art museum, where I saw an interactive exhibit on tasseology, the ancient art of divining the future from coffee grounds. Armenian artists and experts in the craft trained an AI model to read the grounds and generate your “fortune.” Here’s mine.

Humans have never stopped inventing ways to see around the corner: reading tea leaves, casting the I Ching, studying the stars, consulting the Oracle of Delphi, reading animal entrails in ancient Rome, cracking oracle bones in ancient China, turning over tarot cards. Different centuries and problems, but same craving to know what happens next.

But the not-knowing is the human condition. The struggle of figuring it out isn’t a glitch in your life or something you did wrong, but the eternal experience of being a person, where the only way past it is through.

Zooming out like this to begin always helps me. Knowing that people have wrestled with this exact not-knowing for as long as we’ve existed, often on far more life-or-death terms than a career pivot or a crossroads in my business, somehow makes my own version of it feel smaller and more solvable.

2. You’re numb. Clear the mental and physical fog first.

Rest and regulate your nervous system.

If you’re anything like me, when you’re in a career or life rut your instinct is to live entirely in your head, thinking harder, trying to brain-power your way out. I still do this and constantly need to take my own advice. But the first and biggest fix usually isn’t up there in your head at all.

I recently reread the book The Body Keeps the Score by Bessel van der Kolk, and the core idea is right there in the title: your body keeps a running tally of your stress, and when you’re exhausted, wired, tense, and anxious, you physically can’t access what you actually think or feel. You can’t trust your instincts or locate your interests if you can’t even hear them over the noise.

When I quit banking, where I’d been working 80 to 100-hour weeks with my body stuck in fight-or-flight, it took months of sleep, rest, and real relaxation before I could hear my own thoughts again. At one point I even went on a seven-day backpacking trip with no cell service before things finally got quiet enough.

I know what you’re thinking: I don’t have months. You don’t need them. Here are the things that have given me that same effect in bigger and smaller doses over the years:

• Sleep and eat. Actually get your eight hours and eat real food.

• Move. Something physical and intense to burn off the stress: a long run, dancing, martial arts, tennis.

• Get offline and into nature. Phone-free walks and hikes, ideally somewhere out of your city.

• Bodywork and woo-woo resets. Massage, acupuncture, sauna and cold plunge, breathwork, sound baths, sage smudging, reiki, or recreational drugs (be careful, and none of this is medical advice).

• Get it out of your head. Journal, or if free-writing isn’t your thing (it’s not mine), turn on your phone camera and just talk, stream of consciousness.

• Bring in help. Therapy or coaching.

3. Take a side quest.

Stimulate and explore.

Stop trying to solve the problem for a while, and go do something fun or creative that has nothing to do with it.

When you run straight at this kind of problem, you usually get nowhere. It’s the same reason the answer to a hard work problem or a relationship issue tends to show up in the shower, or on a walk, or the second you stop forcing it.

Researchers call it the “incubation effect”: your brain keeps working on the problem in the background once you step away and let your mind wander, and that’s often when the insight actually shows up.

In other words, you need a side quest.

A very random, very incomplete list of side quests:

• Take in art and culture. An art museum, a movie by yourself, a concert or a festival.

• Explore somewhere new. Travel somewhere you’ve never been, walk around a neighborhood you don’t know, or go vintage and thrift treasure hunting.

• Make something with your hands. Creative writing, pottery, painting.

• Learn something random. Show up to a talk or event in an industry you know nothing about but are curious about.

• Go woo-woo. A tarot or astrology reading, a meditation retreat, or plant medicine like ayahuasca (use caution, and none of this is medical advice).

4. Get external input, selectively.

Once you’ve cleared some fog and taken a few side quests, so you’ve got a little distance from the problem, outside input starts to actually help.

A few forms this can take:

• Talk to a friend, or someone who’s walked the path you’re eyeing. A single conversation probably won’t hand you the answer. But your friends see a version of you that you can’t see from the inside, and someone who’s navigated the same thing can tell you what worked for them.

• Talk to someone whose life you find interesting. You might not know what you want, but you probably know a few people who seem energized by what they do. Ask them about it. You’ll learn a lot about what you’re drawn to and what you’re not. If you don’t see someone like this right away, ask a friend to introduce you to someone they think could help. If you don’t know anyone, I interview people in this newsletter with interesting paths - a few places you can start:

  • How to turn your passion into a profitable lifestyle business without burning out

  • How to build a portfolio career by investing in relationship currency

  • How to use a gap year to pivot and rebuild your career

  • How an ex Goldman banker and PE associate broke into startup ops

• Talk to old friends and family about what you were like as a kid. This is getting external input from your younger self. As we get older we lose track of what actually makes us tick, and our talents that showed up early (you always made art, you built insanely intricate Lego sets) usually keeps resurfacing in different forms.

One caution, and it’s why I say to do this selectively: if you lean too hard on other people, whether friends, family, coaches, or experts, you can end up chasing something just because someone told you to, or because it felt assigned to you. That lands you right back at square one the moment you realize you’re stuck again.

And speaking of woo-woo, I created a free career tarot card game to help you start figuring out what’s next! Swipe through paths and tradeoffs, and get a career archetype with practical ideas for your next move.

5. Just try something.

This is going to sound useless to you right now, because your immediate reaction will be “but I don’t know what to even try.” Fair.

So while you’re working through steps 1 through 4, keep a running list of anything that sparks even the faintest interest. Then pick the first thing on it and go.

And if you’re still coming up empty, stop trying to manufacture an interest that isn’t there.

Start with something you’re good at and don’t hate. Do more of it, or try it in a new form. Maybe you’re good at building slide decks at work. That might not feel like a calling, but think…what’s another way to use that skill? Could you make Canva graphics for local events, or build yourself a personal website? Pulling a thread you already have will get you moving faster than waiting around for a brand-new one to materialize out of nowhere.

Silver lining…

When I quit banking, and again during my MBA, the “stuckness” felt enormous, and those pivots felt huge and scary. What I’ve noticed since is that the closer I’ve gotten to things I actually like doing and feel aligned with, the smaller the pivots have become and the less scary each one feels. Really, they don’t feel like pivots and more like small adjustments.

So if the leap in front of you looks massive right now, it won’t always be that way (I think!). The more honest you get about what you actually want, the shorter the jumps get in the future.

If this helped, let me know, and please send it to a friend who’s in it right now (or bookmark it for the next time you are).

The Exit Plan

If you’re actively figuring out your next career move and want a much less woo-woo resource, The Exit Plan is an interactive Notion guide that gives you the structured guide for mapping your exit with frameworks, calculators and trackers that you can work through at your own pace over 5 weeks.

The goal is to get from “I can’t name what I want” to a next move you actually test. I almost ran it as a $400 live cohort, but turned it into a self-guided product so more of you could use it.

The Exit Plan →

• Build a Nonlinear Personal Brand in 14 Days to finally explain your career path and attract inbound opportunities

• The Exit Plan for ambitious people figuring what’s next

• Find me on: Instagram, Linkedin, Tiktok, Youtube

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear route.

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Congrats to everyone who’s graduating in May! I’m at my brother’s graduation this weekend, so I figured I’d take this week’s newsletter as an opportunity to share the recording and takeaways from a Substack Live I did last weekend with Alexis Barber and Simi Shah, two fellow creatorpreneurs who also got their MBAs from Wharton.

If you want the full tea though, you’ll have to watch the live 🍵

For a long time, I was embarrassed to call myself a “creator” after getting my MBA.

Wharton grads are supposed to go into consulting, banking, PE, big tech, or a startup with a real title. Posting on LinkedIn and building a personal brand is not on that list.

It felt weird until I started getting to know Simi and Alexis, who graduated from Wharton the year after me. Simi runs South Asian Trailblazers, an award-winning podcast and media company, and advises C-suite execs on marketing strategy. Alexis hosts Too Smart For This, a podcast with 150+ episodes, wrote a book published by Penguin Random House, and built a creator business after working at YouTube.

Why we went to business school

For me, there’s an official answer I tell people and a real one.

The official answer is that I wanted to pivot into product management. I’d come up through investment banking and tech strategy and ops, and Wharton was one of the only ways to make that move without taking a huge pay cut at a tiny startup.

The real answer is that I was living in Latin America right after the pandemic, it was a lonely time, and I thought business school would be a silver bullet that fixed my career, network, social life, and a lot of other things that were not going so well. (It wasn’t.)

Talking to Simi and Alexis, what came through is that the three of us walked into Wharton from genuinely different starting points. Simi had already built South Asian Trailblazers into a real platform before she applied — a podcast with traction, a growing community, an advisory practice. Alexis came in straight from launching YouTube Shorts at Google, with her own creator work already in motion. Neither of them was using the MBA to find a career. They were using it to build on top of one.

What business school actually gave us

It taught me the thing I thought I wanted was not the thing I wanted.

I got the product internship I’d been gunning for, realized I didn’t want to build products from the back end, and pivoted toward launching and storytelling instead. The silver bullet came as a result of realizing business school was not the silver bullet.

The network also took longer to mean something than I expected. In school you meet everyone, but you don’t really know who’ll stick around until after graduation. Some of the connections that I relate to the most — including with Simi and Alexis — only became real after we were out of the bubble.

One of my favorite moments in the conversation was Simi describing comparing herself to a past version of herself, walking over the same bridge in Philly beause she came out of the MBA more confident in her business and vision.

For Alexis, the MBA was more additive than reinventive. She kept scaling Too Smart For This through school, landed her Penguin Random House book, and treated the two years as a platform on top of what was already working. She talks about her time at Wharton as a chapter where she blended “cultural fluency with strategic rigor” — and that’s a pretty accurate way to describe how she navigted it. She came in with the audience and the cultural read, used Wharton for the operational and strategic muscle, and walked out with both.

Our 3 different post-grad paths

My path was the most typical of the three, at least at first.

After the product internship didn’t pan out, I took a chief of staff role on the go-to-market side at a mid-sized B2B SaaS company. On paper, the dream business school outcome — fully remote, well paid, normal hours, reporting to the CEO.

A couple months in, my very clear thought was: this cannot be it for me. The job was fine but felt stagnant.

Content was the thing I’d been thinking about but avoiding for years. Once I started doing it on LinkedIn — badly and publicly, in front of the same classmates who would actually see me — it became how I got my current marketing job at a startup.

Simi didn’t take a corporate job after graduation. She went full-time on South Asian Trailblazers and her advisory work with C-suite leaders on digital branding and strategic communications. Her business now is a media company, a community, and an advisory practice running in parallel — the podcast keeps building reach, the community deepens the platform, the advisory side monetizes the strategic expertise the platform proves.

Alexis didn’t take a corporate job either. She went full-time on her creator business and has spent the year out of school building it like an actual business, not a brand exercise. The Penguin Random House book is one piece of it. The 11K+ subscriber Substack is another. So is the personal branding coaching she now offers — cohorts, 1:1 work, office hours, a course launching at $500+ — that turns the audience into revenue without burning her out.

So when people talk about post-MBA paths as “consulting vs. tech vs. PE,” the three of us are a useful reminder that it’s also “salaried job vs. founder vs. founder-with-different-business-model.” All three were available to all three of us. We all picked differently.

Why building publicly is so “cringe” in school

Business school loves entrepreneurship in theory, but it has a very specific idea of what serious entrepreneurship looks like.

The classic business school startup is an AI company with a pitch deck, no revenue, and a few classmates nodding about TAM. Meanwhile, Simi and Alexis already had real businesses with customers and revenue — Simi’s podcast and advisory work, Alexis’s media and audience — but the perception in school could be completely different.

If you’re building a creator business, hosting events, or making money from something that looks too internet-native, the questions you get are “Why don’t you just be an influencer?” and “Is this a serious thing?” In the cringe stage, that’s hard to brush off. So I waited until after graduation to even think of building a platform.

At Wharton, I’d hear classmates talk about people who posted daily snippets from their lives. They weren’t even trying to build creator businesses. They were just posting for fun. And people would still talk behind their backs and say it was ridiculous. The thought “who does she think she is?” is everywhere.

How to start creating content from scratch

The first version of my content calendar came from posting my career story on LinkedIn and letting people book free calls with me. I did around 20 of those calls, treated them like customer research, dumped the notes into ChatGPT, and asked what I should post about.

If you don’t want to do calls, the better question is: where does your alpha come from? (Yes, I used to work in finance in case you couldn’t tell!) What can only you say in a way AI can’t copy and a stranger can’t paste into a chatbot?

If you’re summarizing the news or reporting on trends in a way anyone could say, you’re competing with everyone. The better question is what only you can say that the people you want to speak to actually want to hear.

Going to business school can be a source of alpha. So can working at a top company.

Simi has been doing this for years through South Asian Trailblazers, and her advantage is specificity. She didn’t try to be a generalist career platform. She built for a specific community, with a clear point of view about who she was elevating and why, and grew the audience and the advisory book on the back of that focus. Her alpha is the depth of her niche.

Alexis’s advantage is different. She came from inside the platforms — she launched YouTube Shorts at Google — and she now teaches the operational and strategic side of personal branding to ambitious women. Her alpha comes from having been inside the systems she’s now creating on.

The 3 questions to ask before getting an MBA

These are the 3 questions I suggest that everyone ask before they get an MBA:

1. Do you actually need the MBA to pivot into your desired industry or next role?

2. Will it tangibly increase your salary or earning potential?

3. Do you care about the network it will bring you?

Sponsored consultant who doesn’t hate the job and is fine with two years of party adult summer camp? Go.

Trying to break into banking or consulting? Still one of the clearest paths.

Trying to do social media at a B2C brand? Building content on Instagram is probably the better proof point.

Trying to break into tech or startups? Writing thoughtfully on LinkedIn can do more for you than the degree.

I’d be careful about the MBA as a vague “I need to figure my life out” move. The environment will pull you toward whatever everyone else is recruiting for that week.

Simi and Alexis answer this differently than I do, because I came in trying to pivot. They came in to compound.

The three questions above are most useful if you’re using the MBA as a career change, which is how I was using it. If you’re using it to invest in something already running — like Simi was with South Asian Trailblazers, or Alexis was with Too Smart For This — the math changes. The ROI is less about salary or pivot, and more about how the two years compound what’s already in motion: the network, the credibility, the time, the proximity to people you’d otherwise have to chase. Simi has written about her version of this calculation from the founder side; both of them are evidence that the founder version of the MBA decision is a different question than the career-pivot version.

More on this:

• Simi’s article: Was my Wharton MBA worth it?

• Watch This Before You Get an MBA (YouTube)

• Why I went to business school (and my #1 takeaway)

Who goes to business school (and who doesn’t)

People at the very top of their careers, who already have it figured out, usually don’t go to business school.

Business school has a high floor. Most people there have already achieved a lot — Ivy League, banking, consulting, tech. But people running million-dollar businesses or raising tens of millions of dollars are not going to business school.

In some startup circles, especially on the West Coast, you get more street cred for being a business school dropout than a graduate. On tech Twitter, the MBA can actively count against you because it signals you’ve always operated inside the traditional path.

That said, Simi and Alexis are both walking arguments against it — Simi running a media company, community, and advisory practice; Alexis running a creator-author-speaker business with brand partnerships, a Penguin Random House book, and a paying community. Building something during or after business school is evidence that you can do more than collect credentials during it.

The most important thing we each got out of the degree

For all of us, it was the people - genuine friendships, interesting connections that helped us grow our careers and as people, and of course, meeting my boyfriend in my case too!

Follow Alexis and Simi

Alexis Barber

• LinkedIn

• Substack: Too Collective

Simi Shah

• LinkedIn

• Substack: Sense

• Manager, Business Strategy & Analytics – Chicago Bulls (Sports, Chicago)

• Chief of Staff to the CEO – Factorial (HR Tech, Growth Stage, Barcelona)

• Chief of Staff, Marketing – Clay (AI, Late Stage)

• Strategic Partnership Manager, AI Ecosystem – GridCARE (AI/Energy, Startup)

• Applied AI Claude Evangelist, Startups – Anthropic (AI, Late Stage, SF)

• Product Specialist – Sequence (FinTech, Early Stage)

• Strategy/Product Hire – Casper Studios (AI, Startup, NYC)

• The 14-Day Nonlinear Personal Brand Sprint

• Find me on: Instagram, Linkedin, Tiktok, Youtube

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for ambitious people choosing the nonlinear path.

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A few weeks ago, I started building a system I’m calling my AI Second Brain. It’s slowly but definitively transformed how I work and given me hours back across both my 9-5 and my 5-9.

I’ve shared pieces of this on Instagram and LinkedIn but I know not everyone catches everything. I wish I’d done this intentionally three months ago, so if this is the nudge you need to do the same, I’ll be happy to have shared it in detail here!

The problem: your AI sounds like AI when it doesn’t know you

AI generates slop when it doesn’t have context. Over the past year, I’d gotten increasingly frustrated with AI because I felt like I kept having to prompt it the same things, upload the same files, and keep re-explaining that I hate the “not x, not y, but z” AI slop cadence that you see in the worst LinkedIn thought leadership posts ever.

The solution: a second brain that gives your AI context that it can keep building on

What I mean by “second brain” is a folder of markdown files (a fancy kind of text file) on my desktop that any AI agent on my computer can read, that tells it:

• who I am

• how I sound and write

• what I’m working on at my 9-5 and at my 5-9

• what rules to follow

• what skills it knows

That way, when I open a new chat with any AI agent that’s connected to it (ChatGPT Codex, Claude, Perplexity, for example), it doesn’t ask me who I am, what I sound like, or what I’m working on. It already knows.

I built this for my 5-9 after watching my team in my 9-5 do this for the past few weeks, and seeing the dramatic impact it had on making everyone’s AI outputs better.

You can start this in just 45 minutes. The point isn’t building the most sophisticated AI-pilled system out the gate in that time, but rather, having an MVP you can keep improving. The longer you wait, the more daunting it feels and the more you think you have to build before you start. (same goes for building anything new!)

The benefits of having a second brain:

1. It works with any AI you use. A second brain is a folder of markdown files. It doesn’t care which agent you point at it. If you’re mostly seeing Claude content on Instagram, it’s because there are so many Claude tutorials being made there.
   
   **Don’t get locked in, because LLMs are surpassing each other all the time. Lately, I’ve found GPT-5.5 on Codex better and cheaper in token consumption than Claude, which I’d been using up to now.

2. Drafts come back 90% ready, not 30%. When I ask for a LinkedIn post or a newsletter based on my voice notes, my AI already knows my positioning, who my audience is, that I never use empty phrases I hate like “That matters” or “quietly”. I’m editing the last 10% instead of prompt-engineering and context dumping my way to the first 90%.

3. No crossover between your lanes. Your AI stops putting personal context into work emails or work jargon into brand pitches. You can route context to specific tasks.

4. It grows and improves every week. Every new project, decision, or skill file you add makes the next output sharper. After a month, your second brain is denser than anything a fresh chat could replicate, no matter how many files you upload.

What’s in my second brain

The basic setup is simple and similar across other guides on this you’ll see. At the top level, I have 3 core files:

1. IDENTITY.md: Who I am, what I do, what I’m building, what I care about.

2. VOICE.md: How I sound, words I use, words I avoid, sentence patterns, tone, examples of my best writing.

3. RULES.md: The routing layer that tells the AI which files to read for which task.

Then I split my life into lanes, with each one being housed in one folder:

• /work for my 9-5 context

• /content for my creator business

• /personal for values, habits, lifestyle context, and anything else that shouldn’t get mixed into work outputs

• /skills for repeatable tasks

A skill is a markdown file that teaches AI how I do one task. I have skills for things like writing a LinkedIn post, drafting a newsletter, reviewing a brand deal contract, writing a carousel, and humanizing AI drafts so they stop sounding like generic slop.

Instead of prompting from scratch, I can say roughly what I want, and the agent knows which process to follow.

Real example: how I use this system

For this newsletter, for example, I gave Codex posts I wanted to repurpose as a longer guide and sent a long voice note on what I wanted to say in the post. Then it read my newsletter skill, which tells it exactly how to write like me, dozens of my past newsletter samples, which include edit logs that show what I’ve historically cut from AI drafts.

That’s a very different starting point from opening a blank chat and saying, “write this in my voice” and pasting a long prompt.

Of course, I still go through every draft, but it cuts the time I spend writing my weekly newsletter from hours to ~30 minutes.

5 steps to build your second brain

»Here’s the full guide. «

The basic steps look like this, but you don’t have to pay too much attention because the guide includes prompts you can paste into your agent to ask it to guide you on all of these steps.

1. Create the folder and the empty files. Three top-level files (IDENTITY.md, VOICE.md, RULES.md) plus the lane subfolders. Empty .md files are fine. The next step fills them.

2. Run the starter prompt. The prompt in the guide interviews you with a few questions per file and writes your first version in about 30 minutes. You’ll edit and add to it as you go.

3. Add skills as you notice them. Any task you do more than two or three times is a skill candidate. Capture how you do it once, and you’ve taught your AI to do it for you forever.

4. Wire up RULES.md so it routes correctly. Be specific. Something like: “for newsletter writing, read /content + /skills/newsletter, not /work.” This is what keeps the system feeling intentional instead of a pile of context.

5. Run a 15-minute weekly ritual. Block time every Sunday to update what changed: a new project at work, a new positioning idea for content, a task you did three times this week that should become its own skill. Without this, the brain goes stale fast. With it, it gets denser every week.

What I’ve added since the first version

Three things that have made mine better since creating my v1:

Moved the folders from my desktop to GitHub. Once your brain is doing real work, you don’t want it living on one laptop. A private repo gives you version history, a backup, and sync across machines. It also makes you less scared to make big edits, because you can always roll back. If you don’t know what this means or how to do it, ask Chat after you have your second brain and it will show you how!

Let my AI write its own skills. When I find myself prompting the same task three times in a row, I ask my AI to write the skill file for that task itself. The brain grows itself.

Weekly audits. Old context gets in the way of new context. My guide includes a prompt you can give your agent to update the brain itself on a weekly basis.

Further reading and more perspectives on building a second brain

Needless to say, especially if you spend time on X, there are hundreds of people who have started building context for their AI months (probably even years) before me, and mine feels like the tip of the iceberg in comparison!

Here are a few resources I’ve learned from along the way.

• Ruben Hassid on AI workflows for creators and operators - his Substack has a lot of great guides and it’s where I started

• Tiago Forte who first coined “second brain”

• Andrej Karpathy on context engineering and “Software 2.0”

X has the deepest and latest versions of this conversation. Instagram and LinkedIn are downstream of it. If you’re serious about building a second brain, start following people who talk about building in AI there. These 3 are great people to start with, and you’ll be down the rabbit hole yourself in no time.

one last thing…think of AI as your team

The best way I like to think about building my AI second brain is like creating a big Notion space for a team, with all the context that new employees coming in need to know in order to succeed in their roles.

You wouldn’t expect a new editor or EA to do good work on day one without context. You’d give them a doc. You’d tell them how you sound, what you care about, what’s off limits. AI works the same way. It just doesn’t ask for the doc, so most people never write one!

If you’re frustrated with how some people on the internet are talking about AI transforming their work and businesses while you’re still prompting for hours to get the right output, take time this week to start building this. 45 minutes of setup will give you back hundreds of hours over the next year.

If you build one, reply and tell me if it’s helped and how you’re structuring yours. I love seeing how people adapt this and learning together!

» If you scrolled to the bottom, here’s the full guide again! You can copy paste this directly into your agent!«

• Pick my brain here

• Free resources

• Find me on: Instagram, Linkedin, Tiktok, Youtube

Interesting jobs from my network that caught my eye

• Strategic Consultant – Applied Intuition (AI/Auto, Late Stage, Sunnyvale)

• Portfolio Services Partner – a16z New Media (Media/VC, Late Stage, NY)

• Director, Global Markets Operations – Chief of Staff – Visa (Fintech, Public, SF)

• Strategy & Operations – TLDR (Media/Newsletter, Growth Stage)

• Founding GTM, US – Rexi (AI/Fintech, Pre-Seed, NY)

• Entrepreneur, CEO Office – Handshake (Career Tech/AI, Late Stage, SF)

• Open role – Stepful (HealthTech/EdTech, Growth Stage, NY)

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for ambitious people choosing the nonlinear path.

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A few months ago, I wanted to clean out my wardrobe and level up my style as a chronically busy person who hates shopping. I searched “stylists in NYC” on Instagram and found Chelsea Hollenbeck, the founder of Good Lines.

I was initially nervous about working with a stylist (what if we didn’t vibe, what if it was too expensive). But working with Chelsea opened my eyes to two things at once: the value of personal style, and (because I’m always thinking about nonlinear careers and businesses) how intentionally she’d built her lifestyle business after pivoting from nursing!!

What struck me almost immediately is that this isn’t just a job for Chelsea. It feels like an extension of who she is and a true passion. Every part of it feels like only she could be running it.

Even as she was the one asking me questions in our session, I had a running list of my own: how she’d built Good Lines from scratch while still working as an oncology nurse, how she grew it into the fully booked practice, how she hired and marketed. I asked her if I could interview her for my newsletter because she navigated what many of you are thinking about or doing: turning a passion into a real business. I also wanted her style advice for ambitious people, especially after you leave the corporate path.

We talked about how Chelsea went from googling “how do you make a website” after a night shift to where she is today, what taste and curation mean as core business skills (and why they matter more than ever in the AI era), how to build personal style when you’re no longer dressing for a corporate uniform, and the question every aspiring lifestyle entrepreneur should be asking themselves before they start.

Why she quit nursing and how she decided on a styling business

Hannah: What were you doing before Good Lines?

Chelsea: I’m a registered nurse, and I still have my license. I’ll always keep it. That was the very first job I had out of college, and the only job I had until I started this. I worked at a hospital in Minneapolis for seven years.

I felt very burnt out. I wasn’t finding any joy going into work. There was one day I just looked around and thought, I don’t want one person’s life here. I don’t mean that in a bad way at all. Just: this is not what I want for my life.

I’ve always been very creative. I’ve always loved fashion. My mom’s an interior designer. I grew up in Miami, around fashion. It was something I’d always done on the side for friends. As many people can relate to, my parents were very “job stability, education first.” I was actually a pretty good nurse — I did well with patients, I understood the work.

Hannah: When did you know you were going to leave?

Chelsea: One day I just looked at my husband and said: I can’t do this anymore. I had a lot of anger and resentment inside myself. Why did I choose this? Now I’m stuck forever. All I have is a nursing degree. I can’t do anything but be a nurse. I had a full-on midlife crisis at 28. I’m 32 now.

Hannah: What got you from that realization to doing something about it?

Chelsea: In October 2022, two months after we got married, I worked a night shift, came home, and just Googled, “how do you make a website?” I made this janky little website. I was like, I’m going to start doing what I do on the side for my friends and family. I’m going to make it full time. I don’t know what the hell I’m doing. And I just started.

Eventually I quit. My husband and I moved to New York City. He’s a pilot for Delta, so he can live anywhere. I said, I want to move to New York. I don’t want to live in the Midwest anymore. I’m originally from the East Coast. That was it. One of the craziest decisions we ever made. It almost broke us. There was a lot of risk.

Hannah: Were there other things you toyed with, or was it pretty clear from the start that styling was what you’d go after?

Chelsea: It was kind of fashion-related for a while. I thought about doing secondhand shopping, being a curator for vintage pieces. I have a great eye when I thrift. Maybe I’d have a vintage shop and style people through it.

I also toyed with getting my Botox license and offering styling on the side. My business name, Good Lines, was actually because that’s what I wanted to name my Botox business. We have lines on our face, and I’ve always been very body positive. I’m more of a natural person and I didn’t go down the Botox path. But I kept the name. Style is linear too, in the sense of figuring out where the lines on your body are, where your hips fall in relation to your ankles, where everything sits. That’s the formula. And our bodies are beautiful, they do great things for us. So, the name Good Lines stuck.

Side hustling for two years before going full-time

Hannah: How long did you side hustle, and what was the tipping point to go full-time?

Chelsea: I did hybrid for the first two years of the business. The tipping point was when revenue was enough for me to justify not picking up the nursing shifts. My husband and I talked about it financially, what made sense for us. I had a goal number. When I finally hit it consistently for a few months, I said: I think I can make more. The only reason I’m not is that my time is only 50% on this.

Hannah: What did the side hustle look like day to day during those two years?

Chelsea: I was fortunately in a nursing job where I could work as much or as little as I wanted, kind of per diem. After we moved to New York, I worked as an IV nurse for a private company, going to homes and apartments to give IVs to people who were hungover or sick. I’d run around the city with my little suitcase part-time while I was building my website and making content. I was living two lives.

Hannah: And how did you make the actual call to go full-time?

Chelsea: Eventually I decided to stay employed by them but didn’t pick up any shifts for a month. I just wanted to see how it went. I gained a lot of new clients in that month, and I just took the risk.

You have to see enough clarity to know it’s pointing in the right direction, but there’s always going to be an element of risk. It’s never just, “now’s the time and it’s going to work.” It’s making an educated guess, like you would for anything.

Transferable skills from nursing to running a styling business

Hannah: Did you ever feel guilt or shame about making this pivot?

Chelsea: Absolutely. There’s already a lot of unspoken hierarchy in nursing culture. ICU nurse versus med-surg nurse. Nurses who’ve worked 25 years versus five years. “I’m a tougher nurse than you because I stuck it out.” To me that’s complete BS, because every nurse plays a pivotal role in the patient experience.

I felt like I was wasting the gift my parents gave me of college. Now I have this degree I’m not using at all. And I felt: who in the world would ever want to hire me? I didn’t go to fashion school.

In the beginning I felt like a poser. I felt shame, embarrassment. I was like, who do I think I am? I belong in scrubs and back in the hospital. That’s what I chose, now I’m stuck. People judged me. They said, “you’re leaving nursing? That’s weird.” Nurses are very tight-knit — they hang out together, do everything together. I didn’t feel supported. I had to get through all of that.

Hannah: What surprised you, looking back, about how nursing prepared you for running this business?

Chelsea: My nursing career parallels what I do now in a lot of ways. Nursing taught me time management, leadership, communication, and how to match what a person needs.

I have clients who are quiet, low-key. I have to match that energy. In the hospital it was the same. Some patients you could drop F-bombs with, super casual. Others were very type A, family observing every little thing. You have to be a chameleon. I’m able to mold to my clients’ needs the same way.

People talk about their bodies. They talk about their insecurities. These are things I talked about with patients too. The communication, the time management, the ability to wear multiple hats. That’s what made me a stronger business owner.

The styling is the easiest part of the job — and the fun part. It’s running the business that’s more difficult, and that’s where my nursing skills come in.

Getting her first clients and networking her way into NYC

Hannah: How did you get your first clients?

Chelsea: My very first client was a friend of mine. Another nurse, but at a different hospital. She followed me on Instagram and was like, “I love that you’re doing this. I always admired your style. I’ll pay the 50 bucks. Let’s do it.” That was my first review.

Then someone found me on Instagram completely randomly. At the time I was living in Minneapolis. We did in-person shopping, and I got photos of her, and I started building a portfolio.

A friend referred me to someone she knew, a woman in private equity, very high profile. She referred me to a couple of other women. It started to grow.

Then we left Minneapolis, so I had to do a whole new networking push.

Hannah: How did you build a network from scratch when you moved to New York?

Chelsea: When I first moved to New York, I went to a networking event the second day we lived here. I had boxes to the ceiling. I went to that event and thought: I should just make my own networking group. So I made one. I ran a networking event every month for a full year.

It was a way to literally make friends, because I’d just moved here and didn’t know anyone. It was also a way to show my presence. I had this blank slate of New York. No one knew me, I didn’t have that nurse tie anymore. I met a lot of incredible women at those events, and I made some very lovely friends I’m still close to.

Hannah: Looking back, was there a habit from those early years that mattered more than you realized at the time?

Chelsea: Once you get the ball rolling, you have to pay attention to when things are coming at you and grab them. The window is small. Whether or not you do anything with it, you at least have to see what’s behind it.

I’ve responded to every single email I’ve ever gotten. Always. Especially in the first few years, because I did that and didn’t ignore some of them, there were a couple I was doubtful about that ended up being some of the largest catalysts of my business.

How she figured out content and built a recognizable brand on Instagram

Hannah: Your content is how I found you in the first place. How did you figure out what to post?

Chelsea: Content has always been hard for me because it takes a lot of planning. (I’m not a content queen like you.) But I started doing get-ready-with-me videos and client transformation videos. I had a part-time assistant, a student, who came and followed me around taking videos.

Now I have someone designated to help with content. I’ve thought about taking it a step further and having a full-time team do it. I think it would help the business grow. I just mentally have to prepare to schedule time for content, which I’m not super interested in. But social media is a huge way to grow your business.

I looked up the popular hashtags for my field. I tested out different types of videos. Whichever ones got more positive feedback (comments, shares), I’d follow that trend for a while.

Hannah: When did you start thinking about your page as a brand and not just an account?

Chelsea: I decided my page should look like a brand. I keep it cohesive: same color palette, similar font, all of that. It makes your business look more professional. It legitimizes what you’re doing. You want people to remember you by something. A color, a font, your face. It’s like Coca-Cola or the McDonald’s arches.

How she protects what she loves from becoming what burns her out

Hannah: It’s clear you love what you do. How do you protect the thing you love from burning you out?

Chelsea: You have to set boundaries and allot time for yourself. Whether it’s “I’m closing the computer at 6 o’clock” or “I’m not taking on this client again because they were unkind to me.” Those boundaries matter.

Hannah: What about when the thing you love is also part of the work, like shopping for you?

Chelsea: If it’s something you’re passionate about, you have to make time to do it just for you. I love to shop — I could easily find something for myself when I’m out browsing for a client. But I try not to. I’ll go Saturday morning by myself, just to see what I like. No clients, no agenda. That’s how I keep the joy in it.

And the power of saying no. Sometimes that’s the whole answer.

How to build personal style after the corporate dress code disappears

Hannah: A lot of my audience is leaving traditional corporate jobs and the dress code that comes with them. If I’m thinking about style as my own (as opposed to tied to a job), how would you suggest someone start designing that from first principles?

Chelsea: The cold hard fact is that we walk out of our homes every single day and we have to put clothes on. How you show up and how you want to represent yourself, unfortunately, is very important. I wish we could all wear a brown paper bag, but that’s not the reality.

I think it’s important to stop seeing it as “oh, that’s a fashion thingy” or “I’m not someone who cares about that.” You don’t have to. It doesn’t have to be an interest or something you keep up with. But dressing a certain way commands a presence. It helps show your personality. It builds confidence.

The clients I have who care less, when they put on outfits I help them with, they tell me, “oh my god, I felt so good in that presentation today, because my outfit was so good.” Not because they were thinking about their outfit. There was just something that made them feel like, I have this.

Especially as a woman in a position of power, or in a male-dominated field, the way you show up is really important. The first thing people do when they see you is see you. Visually. Before they hear your voice or anything else. It’s what you look like when you walk into a room.

I try to help people think about it less as “being a fashion girly” and more as: what is your presence? What message do you want to convey when you walk into a room?

Hannah: What’s a practical first step for someone who wants to start being more intentional about it?

Chelsea: Take a look at your closet. Separate what you actually wear from what you don’t. Look at the pieces you reach for and find the correlations. Is it color, pattern, fabric? When you understand what you actually wear, you become a more educated shopper for yourself.

There’s a way to bring color into a professional setting, by the way. A lot of clients say to me, “Chelsea, I love color, but I work in a corporate job and I feel like I have to wear black.” That’s not necessarily true. There are ways to keep things professional while letting your personality show.

I also tell people: try things you might not normally try. You don’t know how you’ll feel in something until you do.

Why taste and curation matter more in the AI era (and how to develop them)

Hannah: Your entire job is taste and curation. In my world, people are talking about taste and curation as one of the most important skills in the AI era because AI can generate anything but it can’t tell you what’s good. What does taste mean to you, and is it something people can develop?

Chelsea: It’s not really something I think about consciously. Like anything, people have their niche, their talents. A good singer is just a good singer. They can improve with a coach, but they’re always going to be a good singer. Someone who can’t sing just can’t sing.

I think taste is more innate. Curation is more learnable.

Taste, when I shop for clients and style them, is truly a feeling. I visualize the person in the item — their personality, everything we discussed. That’s how I know. I’m like, you know what, I really think she should try this. He should try this.

Hannah: How would you describe curation, then, since that’s what people can develop?

Chelsea: Curation is more like having an outline of what it is you need. Like if you’re cooking a meal and you need a recipe, you have to find the ingredients. If you’re looking for a vintage item, you do your research on top vintage sellers. You look at different neighborhoods. If you want a higher-end thrift item, you go to a thrift shop in a wealthier neighborhood. Curation can be learned.

Chelsea’s #1 advice for turning a passion into a business

Hannah: What’s your number one piece of advice for someone with a passion (styling, fitness, cooking, design, whatever) thinking about turning it into a business on the side?

Chelsea: Just rip the band-aid off and do it. That is my absolute best advice. Never take no for an answer. Just do it. Don’t care what anybody says or thinks about you.

It’s going to be shit in the beginning. It’s going to be hard and weird. You won’t know what you’re doing. But the difference between the people who succeed and the people who fail is that the ones who fail give up. Don’t give up.

Connect with Chelsea on Instagram and at Good Lines!

• Pick my brain here

• Free resources

• Find me on: Instagram, Linkedin, Tiktok, Youtube

• Strategic Consultant – Applied Intuition (AI/Auto, Late Stage, Sunnyvale)

• Portfolio Services Partner – a16z New Media (Media/VC, Late Stage, NY)

• Director, Global Markets Operations – Chief of Staff – Visa (Fintech, Public, SF)

• Strategy & Operations – TLDR (Media/Newsletter, Growth Stage)

• Founding GTM, US – Rexi (AI/Fintech, Pre-Seed, NY)

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for ambitious people choosing the nonlinear path.

Subscribe now

In April 2025, I hit 100,000 Instagram followers after creating content for 6 months.

By December 31, 2025, I’d barely grown, ending the year with just under 110,000 followers.

This year, I’ve grown to 180,000 in 4 months.

That’s 70,000 followers in 4 months, after about 9 months of near-flatlining.

Engagement followed the same shape: dead for most of 2025, then back.

Brand deals followed too, including the biggest single deal of my creator career so far (multiple five figures for 1 video), alongside others with OpenAI, Anthropic, Amazon, Microsoft, and LinkedIn.

I didn’t write this to brag but to offer a candid reflection and tactical guide for anyone creating content in 2026, especially if you’ve hit a plateau, are shifting niches, or are trying to reposition yourself. Because 6 months ago, I didn’t think this was possible.

This is specifically about my experience on Instagram, but 90% of the advice applies whether you’re building a personal brand for your career, for a creative pursuit, or as founder-led content for a business you’re growing.

If you’re completely new to content creation, you might want to start with the piece I wrote last year on building my content business from zero as a 5-9 creator. I cover how to get started when you have no idea what your content should be about, who your audience is, or where to reach them. Think of this as Part 2, but it’s still legible if you haven’t read Part 1.

Why I wasn’t growing

Before I could reposition my content and grow this year, I had to examine what was going wrong, both qualitatively and quantitatively.

I had started my content journey in 2024 by sharing “career advice”: leaving investment banking, breaking into tech, tactical job-search tips, and reflections on business school.

I had momentum from going viral in late 2024, an audience I’d grown into, and a sense that I’d “found” my niche.

The problem was that the niche I’d found, and the story I told (”career pivots and leaving banking for tech and getting an MBA”), had gotten stale. I was talking about breaking into tech and finding a new job when tech was laying off thousands of people every week.

At the same time, I left a big tech company for a startup and focused more on the creator economy and my 5-9 personal brand than on building a “corporate career,” even though that was still much of the content I created.

But I’d been told (and told myself) that you have to stick to your niche, post consistently, follow the formats that work, and not confuse the algorithm.

So I posted what I thought my niche demanded. It felt mechanical, and it became a vicious hamster wheel: I wasn’t excited, so the content wasn’t great, so it didn’t do well numbers-wise, so I felt more pressure to post things that “worked,” which made me less excited.

By the end of 2025, I’d convinced myself I’d plateaued, that people weren’t interested in what I was saying anymore, and that I’d probably exhausted my creator lifespan. I thought I should happily accept that this was a side project I’d make a bit of money from and leave it at that.

To reinvent yourself, you first need to reset and reposition

The result of the vicious hamster wheel was that I was unmotivated to create. I couldn’t open the camera, never wanted to hit post, and didn’t even want to scroll because I felt so stagnant compared to other creators. But I also couldn’t get off the hamster wheel, so I kept making mediocre things.

What forced me off it was taking a 2-week vacation at the end of the year, saying “f*ck it,” and scheduling my top 10 past-performing videos as reposts.

What started as a way to avoid creating turned into a way to examine what excited me and what didn’t about the content I’d made in the past. An audit and a recalibration.

And what moved the needle was realizing I’d been focusing on a “niche” when I should have been focusing on my audience and my positioning.

A lot of people use “niche” and “positioning” interchangeably but they’re not the same. Your niche is the topic you cover. Your positioning is what makes your content different from everyone else’s when you speak to a specific audience, because of what you uniquely offer that’s distinct from what’s already out there.

I needed to reposition. And to do that, I had to go back to my audience and ignore everything else: my old content, other creators, the algorithm.

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear route.

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“Every nonlinear career path eventually leads to entrepreneurship.”

Last month I was on CAPS LOCK, Sam Feher’s podcast for ambitious people who want to live bigger, better, louder, and longer…and this is what we concluded, as two creatorpreneurs with very nonlinear careers.

Sam’s career is more nonlinear than mine. She started her career at Cosmopolitan, worked in social media for Cynthia Rowley, built her own wellness-focused personal brand, founded a creative agency and a clothing brand, and hosts her podcast.

What I loved most about this conversation is that true to nonlinear form, we covered a LOT of ground:

• Quitting too early and what I’d do differently

• Why my chill fully-remote tech job drained me just as much as banking

• How to figure out what’s next

• How a Saturday night video I made while painting my nails that got me 50k followers and kickstarted my content business

• How to build a personal brand in 2026 when everyone’s already doing it.

If you’re on a nonlinear path, figuring out what’s next, or thinking about how to stay relevant as AI changes everything at work, I hope you’ll find this useful!

I quit my dream job without a plan…twice

Sam: How did you know you were ready to leave your dream job? Did you have a rubric, a pro-con list? Or did you just reach a breaking point?

Hannah: Definitely more of a breaking point. And I’ll be honest with you: I think I quit too early. For a long time after, I thought I made the wrong decision. I wished I had stayed a little bit longer — not because I wasn’t going to leave, but so I could have made a plan.

I’ve done this twice. The two instances where I really felt like I am not in the right place were very different from each other. Coming out of banking, that was just the hours, the toxicity, the burnout. But then last year, after I graduated business school, I was working in a high-paying, very chill, fully remote tech job. And somehow that job drained me. It drained me because I felt stuck in place. I was not growing, not learning. It felt like such dissonance because it wasn’t a burnout situation. It was the opposite.

Sam: So burnout the first time, stagnation the second. The second time, it sounds like you had something in mind for what was next, and that’s what gave you the confidence to leave.

Hannah: Yeah. And I think the readiness thing is — a lot of us, especially high achievers, we don’t listen to our instincts. But at the end of the day, you know. You really do know. You can do all the pro-con lists on paper, make all the plans, but what you really need to do is take that first step of action. And sometimes the drastic decision to quit isn’t the right action. The right action might be: what’s one small experiment I can run? Who can I talk to that will give me some clues? It’s not always just, I’m going to up and go. Because that’s going to make you feel like you failed. Financially insecure. Incompetent. There’s a lot of imposter syndrome that comes with that too.

The $250k concept I filmed while painting my nails

Sam: A lot of people take away very different things from their MBA. I’m curious if there are things you learned that you use constantly now, across multiple roles.

Hannah: Something I learned in business school is literally the entire reason I have the personal brand and content business I built today. I know that sounds crazy, but one of my earliest videos — maybe a month into creating content — completely blew up my account and got me 50,000 followers. Not even kidding.

It was about this concept in negotiation called BATNA. Best Alternative to a Negotiated Agreement. And this was one of my lowest-production videos ever. It was a Saturday night and I was painting my nails.

Sam: It’s only those that blow the whole thing open.

Hannah: Always. And I was like — I paid $250k to learn this in my MBA. BATNA is basically the idea of having a plan B and not selling yourself short in any situation. If you and I are negotiating a job offer, I have a good BATNA if I have another offer on the table. I think it resonated with people because so many of us are used to chasing rather than attracting opportunities. The whole concept of having a backup is: you always need to shore up your other options. Your full-time job — you cling to it because it’s the thing that pays your bills. But as soon as you start building something on the side and you have something else, it just completely changes your mindset. It’s the same with relationships, even with having social plans on the weekend. The principle is everywhere. I paid $250k to learn it at Wharton and made a video about it on a Saturday night.

Banking → tech → MBA: a path without a plan

Sam: So you leave banking, you travel, and when you came back, did you start in another job or go straight to Wharton?

Hannah: I had a job between traveling and Wharton. After I quit investment banking, I thought — you see stuff in the movies, right? You see Eat, Pray, Love, and you’re like, I’m going to go to Argentina. I’m going to find myself. I’m going to climb the mountains and that’s going to be great. It’s just going to all be suddenly clear. I’m going to reach some sort of epiphany and figure it out. No, of course that didn’t happen.

Being in nature did help me think more clearly. When you’re always hunched over a computer and your brain cells are getting fried, putting yourself in nature gives you some clarity. But that doesn’t mean it’s going to just inception you into the right next thing.

Honestly, I went through months of just: what am I doing with my life? I quit what might have been the best-paying job I’ll ever get. I can never go back to finance — I completely burned that bridge. What am I going to do?

So on one hand, I started figuring out the business school process, because that’s just what a lot of people do. And on the other hand, I started panic mass-applying to jobs. Hundreds of jobs that had nothing to do with one another. I’ve never shared this on the internet, but I was deciding between a startup in Latin America and a social enterprise in Southeast Asia — two completely polar opposite things, completely polar opposite lifestyles. I think there was also a video game company in the US doing strategic finance, which I knew I didn’t want.

Sam: No way.

Hannah: Three completely different timelines. It truly felt like throwing darts at the wall. And I was very lucky because the dart I threw landed me in a really interesting startup position in Mexico City where I ended up working in two or three different roles just because of how fast the company grew — not because I asked to move, just because the business needed it. I got to try a lot of different things without switching jobs and having it look bad on paper.

Sam: And then when you went to business school — was it more figuring out what you want, or more achieving something you already knew you wanted?

Hannah: More the second thing. And this is something I talk about in my content a lot: when you go into investment banking, when you go to business school, it’s for prestige, at the end of the day. I think some people have their head in the right place — they know they’re doing it for a few years because it’s going to get them somewhere they actually want to go. But for me going into banking, I just thought: I’m going to do banking, figure out whatever’s next, make a bunch of money, and get out. No real plan behind it.

For business school, I did have a sense — I wanted to pivot into product management, which I’d done a little bit in my prior role but wanted to do at a bigger company. And business school is a great way to do that. I did achieve that goal. My summer internship was in product management. And through that, I realized I didn’t want to do it.

Sam: And that’s the only way you’ll ever know.

Hannah: It’s a little embarrassing to admit after all that. But yes.

I started posting about nonlinear careers because I was embarrassed by mine

Sam: I feel this guilt and shame about my nonlinear career all the time. So it was funny watching your videos — you’re out here celebrating this thing I’ve always felt so insecure about.

Hannah: I got to be honest: the reason I first started posting about having a nonlinear career is because I felt that same embarrassment, that same imposter syndrome. It was almost a way of gaslighting myself into believing — oh, you know, this is fine. And then more strategically, rebranding myself a little bit. When you have an experience that people don’t immediately get, you have to be your own PR person.

The funny thing is, in the process of gaslighting myself, I did end up truly believing it. Because I saw the results. And because the world started changing around us.

One of my favorite books on this is Range by David Epstein. He goes through history and shows all these examples of people who, because they had experience in different fields, went on to make great inventions or discoveries because they brought something in from a different domain. His idea of the spiky generalist — someone who can do a lot of things but is quite good in one or two specific areas — that’s the sweet spot. Because it is so hard to be number one at one single thing. But if you can be great across a bunch of different things and particularly good at one or two, that’s a real edge.

And here’s what I figured out about my own path: my day job is product marketing for a technical fintech startup, which means I’m learning how to tell a story, reach an audience, and sell something. My content does the same thing. The newsletter does the same thing. The speaking does the same thing. It’s all building the marketing muscle — I want to become so good at this craft across different parts of it. On paper, it looks like my eggs are in different baskets. But it’s the same basket. These things compound.

Sam: The “jack of all trades, master of none” quote — people only ever say the first half.

Hannah: Right. The rest of the quote is that the jack of all trades is often better than the master of one. And the broader context is that the world is changing around this anyway. Fewer people are in siloed specialist roles because AI makes it easy for everyone to be both a generalist and a specialist at the same time. The more narrow and defined your role, the easier it is to automate, because it’s repeatable patterns. There are going to be more spiky generalists because the shape of work is changing.

Sam: I’m also curious about something in your content — you had this post about the risks of maximizing and optionality. You believe in nonlinear careers, but not necessarily in keeping all your options open. Why?

Hannah: I think maximizing is this idea that you’re always looking for the next best thing — the objectively best option, not what’s actually best for you. From a career perspective, it’s like: I don’t know if I should take the marketing job or the product job or apply to business school, because I can’t figure out which one is truly the best. It’s not listening to what you actually want. Whereas the nonlinear or multi-hyphenate path is more — how am I leaning into my curiosity for what’s next and building toward the next thing?

A lot of high achievers have this maximizing tendency, and at the end of the day you just have to maximize for what is good for you. Once you’ve made the decision, be happy with it and understand that you made the best decision for you, rather than trying to find the objectively best outcome.

Why every nonlinear path leads to entrepreneurship

Sam: I have a two-year threshold in every role. At two years I get restless, start looking around. And for the longest time I just beat myself up over it. I internalized it as not having discipline.

Hannah: I think what it’s really telling you is that you’re destined to be an entrepreneur. And over time, your pivots and your experiments and your iterations become smaller and smaller. Earlier on in your career it might be this massive leap — investment banking to a no-name startup in Mexico City. And now it’s like, okay, maybe I change something within my content. It can feel like a pivot in the moment, but the moves become more precise. You’re circling closer and closer to the thing you actually want to build.

I think about that with my own content journey too. I honestly doubted I would stick with it at the beginning because so many people drop off. But over time, the shifts within my content have gotten smaller and smaller. You’re not less disciplined for having the two-year itch. You’re just getting more precise about what you’re building toward.

How to be high agency

Sam: I want to know how we become that high agency person. Because for me, agency is very low on my values ranking. My authenticity gap is negative — I’m expressing too much agency. I’m sick of making all the calls. I just want someone to tell me what to do for once.

Hannah: Being high agency can be exhausting, and that might sound contradictory. But I think in order to be truly high agency, it requires knowing which parts of your life you want to dedicate that agency to. Some of that is removing decision fatigue around things that don’t truly matter. The high agency is also knowing what to prioritize. In my personal life, I honestly don’t plan a lot. I’ve got a planner at home — that’s my boyfriend.

I think the most important thing is a bias for action. You don’t sit and mull on something to the nth degree. After you have enough of a plan and enough of a strategy, you take action. But there’s a flip side — if you only ever take action without any strategy and execute poorly, that’s not high agency either. It’s more: how do you go about finding the tools and resources to get something done? The best description I’ve heard of this is the person you’d call if you were stuck in a jail cell in a random country. Who would get you out?

And I find it increasingly hard to be around low agency — you see it in the workplace where people come to you with problems instead of solutions. High agency people get things done before they’re even asked.

Sam: I think the smartest people in the room do enough research to make a decision, and then they make it the right decision — instead of secondguessing it endlessly.

Hannah: 100%. If you’re truly agonizing over a decision and both paths seem good, the one you pick will be the right path because you’re going to do everything in your power to make it the right decision.

In the context of AI, being high agency comes down to this: some people are never going to open Claude or ChatGPT until someone forces them to. Then they’ll use it like a chatbot and never take the extra step to figure out what it can actually do. That’s where the gap is going to widen — between people who learn these tools and people who just sit and wait.

Building a personal brand in 2026

Sam: How do you approach building a personal brand in 2026, with all this noise and everyone doing it?

Hannah: The first misconception is that everyone has a personal brand already. How are you perceived? What do people think about you at work, with your friends, with your family? That already exists. What we see online — the LinkedIn presence, the Instagram, the newsletter — that’s the amplification of your personal brand, not the brand itself.

And what your goal is behind building one matters a lot. If you’re pivoting into a new field and want to show how your past experience is relevant, that’s probably LinkedIn. If you just started a small jewelry business on the side and you want to drive leads to your business, Instagram — maybe TikTok — is the way to go. The tool follows the goal. Most people who say “build a personal brand” have collapsed the whole thing down to one channel without really understanding what they’re building toward.

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Alex McCann has never had a corporate job. He studied music. He ran a boutique marketing agency that didn’t work out. He digital nomaded across Latin America with friends who quit their jobs to come with him. And then he wrote a Substack post called “The Death of the Corporate Job” that got 17,000 likes, got picked up by The Times, and somehow led him to a call with the CEO of Bayer. Then he build an AI career platform.

None of that was his plan. His plan (if you can call it that) was to document what he was learning in real time and see what happened. After his Substackpost blew up, he did something I think is underrated (and exactly what I did before I first started creating content): he opened his calendar to strangers, took hundreds of calls over two months, and used every conversation to understand exactly what people were stuck on. That research became Rumbo, an AI career tool built around the idea that most people aren’t asking the wrong question, but answering it in the wrong vocabulary.

Alex and I connected through our career-related content, and I’ve been wanting to have this conversation for a while. So many of you are in corporate jobs that feel like they’re running out of road, and so many of you want to build something but have no idea where to start. Alex has thought about both of these things more carefully than most people I’ve spoken to.

Whether you’re thinking about your next career move, figuring out your next creative direction, or building your own product, I think you’ll get a lot from our conversation.

From engineering to music to founder: the long way around

Hannah: You’ve made so many pivots: engineering to music to creative director to now founder and content creator. A lot of my audience has been in the same job for years while you’ve done all of that. How did you get clarity on what the next step was every time? And how did you get the confidence to actually go do it?

Alex: It was a combination of things. I really believe in this idea from the book Tiny Experiments, just trying things out. That was something I didn’t realize was a skill, but I had always just been somebody who would give stuff a go. And that coupled with a really intense curiosity, just asking a lot of questions of myself and other people. I think that was what allowed me to pivot quickly.

I also have to acknowledge that I was young and didn’t have any responsibility, so I could take on a lot of risk. But the culmination of voracious curiosity, willingness to try things, a kind of attitude of I’m just going to try stuff and then see what happens, and circumstances that allowed that to happen. It was a combination of luck and people around me encouraging that curiosity.

Hannah: Did you ever fear that by switching from engineering to music, or music to creative, you were throwing away all the work you’d done previously?

Alex: Yes, a little. I never got so into it that there were too many sunk costs. The biggest shift was definitely the move from engineering to music, because up until that point my whole life I had really identified as an academic person who loves this type of thing. I had crafted my identity around what I thought I was going to be. And then when it all came crashing down, there was a real identity shift. That was hard.

I was pretty early on clued into the idea that qualifications were less valuable than they used to be, and the corporate ladder wasn’t what it used to be. So the sunk cost piece was less of it. But I definitely felt the weight of the identity changes that came with the pivots.

Building the content muscle before anything went viral

Hannah: You said several times that you were really lucky. And I’m sure you feel that way, and you’re a humble person. But luck only shows up when you’ve done the work to maximize your surface area of luck. Every piece of content you post is a lottery ticket. How did you first start creating content? What was your initial goal with it?

Alex: I want to give myself credit for two things. One is the beginner’s mindset. When I started my first business, I went to a lot of networking events and I was often the youngest person in the room by a lot. The mistake a lot of young people make is going into those rooms trying to show what they know. I didn’t have that. I went in with an attitude of: you’re the expert, I’m the beginner, can I just ask you questions? That gave me access to people who ended up being mentors because they were interested in helping someone who was genuinely curious rather than performing confidence.

And the second thing: opportunity is a function of density. When you’re young, one of the best things you can do is just put yourself out there in whatever form that is. Networking events, content, reaching out to hundreds of people every week.

How I got into content: that graduate job I mentioned introduced me to personal branding because I was doing some LinkedIn posts for the founder. An early mentor said to me, you’re in a really steep learning curve right now, why don’t you just share what you’re learning and see what happens? So that’s what I did. And I started to get some traction. Nothing like now, but it helped me build the muscle.

Then I stopped for a while while I was traveling and working a previous role. And when I started this new venture, it felt like second nature. I thought, okay, there are interesting things I’m learning, interesting things I’m seeing, let me just put it out there. My coach was also on Substack and said it’s a good place for a slightly different style than LinkedIn. So I did. And yeah, rest is history.

Hannah: I love that you were documenting your learnings in real time. That’s the thing people don’t say out loud: most people who build a personal brand, it’s not their full-time job. The best approach is to document what you’re already doing, so it doesn’t feel like every post is a fresh thing you have to invent from scratch.

Alex: It’s like what they say about musicians. In the early stages, their work is the best because their proximity to real life makes it relatable. And then as they get successful, that proximity disappears and people stop connecting with it as much. When people are really in the thick of something, building a product, learning from a day job, it’s stuff people can relate to. It feels more authentic. And I can imagine that when your whole job becomes content creation, it gets harder to maintain that.

The viral Substack post and the CEO of Bayer in his DMs

Hannah: Your Substack post “The Death of the Corporate Job” had 17,000 likes. I usually get 50 likes on my posts. What was the core idea, and why do you think it resonated the way it did?

Alex: It came from reading Moral Ambition, which I highly recommend. The author talks about this idea that so many highly ambitious, highly intelligent people end up in what he calls bullshit jobs, this Bermuda Triangle of meaninglessness: corporate finance, banking, corporate law. And I remember reading that and seeing the people around me in my life who were so intelligent, so ambitious, great university degrees, genuinely kind and generous people, and yet the system had incentivized this particular kind of work, and the corporate ladder was still being sold as this glamorous journey.

I just thought there was something so different between the narrative around corporate work in media, from our parents’ generation, and the people actually living it. I wanted to uncover that and be honest about it. Why is the system set up to reward something that is so clearly not what it’s perceived to be? And what does the future look like? Because part of what I was writing about is that this understanding of the corporate ladder is changing anyway. It may not even be on offer to people who are interested in that path.

Hannah: And you’ve never had a corporate job. How do you think about those two things being true at the same time?

Alex: Totally get it from the people who’ve criticized me for that. Two things are worth saying. First, I was hearing this from so many people, so many conversations all coming to the same conclusion. I was prepared to be wrong. But the response felt like proof of concept, because so many people put their hands up and said yes, this is true to my experience.

The second thing is the fish in water observation. People who are inside the corporate machine get so heads-down, engrossed in the culture and the language, there’s this whole corporate vernacular, that sometimes it takes someone from outside to point out something that’s actually pretty obvious to the people in it. I was hearing a lot of the same thing from a lot of different people, and I thought: let me just put my observations out and see what they think.

Hannah: What was the craziest thing that happened as a result?

Alex: The press coverage was wild. The Times did a roundup of articles to read in 2025 and it was one of the top ones. The Free Press feature the same weekend they were acquired blew up too. But the craziest one was the CEO of Bayer reaching out.

This person messaged me on Substack with no profile picture, no context, said their CEO wanted to chat if I was interested in interviewing him. I was pretty doe-eyed about the whole thing at that point, said sure, put it in the calendar a few weeks ahead, and forgot about it. Then the weekend before, I’m looking at my calendar and I see this interview pop up. I looked it up. Bill Anderson. CEO of a company with nearly 100,000 employees, one of the biggest pharmaceutical companies in the world. And I had just casually booked it like it was nothing.

But honestly? The craziest thing is being at events now and having people I’ve never met turn to me and say, oh yeah, I’ve read your article. That still blows my mind.

How he turned 17,000 likes into hundreds of 1:1 calls and (eventually) a product

Hannah: You didn’t just double down on Substack after the post blew up. You had a really intentional approach to figuring out what to actually do next. Walk me through that.

Alex: When the article went viral, I knew we were going to build the platform, but it was really early stages. I didn’t know exactly who it was for or what it might look like. I asked myself: since I’m not the one building it, what’s the most impactful thing I can do? And I thought: understand the problem from every possible angle.

So I put out a link to my calendar and said, if anyone wants to chat, just book some time. I’m not a career coach, I’m happy to just be a sounding board. And it went crazy. Hundreds and hundreds of people booked calls over the next couple of months.

One of the things that kept coming up was that people had started using ChatGPT to help them think through their careers, but they were still lost. ChatGPT as a conversational partner can only respond to the quality of input you give it. And if you don’t have a clear understanding of what is likely to bring you career fulfillment and meaning, the results you get back are going to be pretty limited. So that was really interesting to me: people are open to exploring this with AI, but it’s not quite there, it’s missing something. And that’s where we landed on the idea for Rumbo.

Alex’s advice: Stop seeing your career as your CV

Hannah: Last question. For someone in a corporate job who feels like it’s slowly dying, but the paycheck is real and they feel stuck, what’s your number one piece of advice?

Alex: The number one problem I see is that people think about themselves through the lens of their CV. When I ask people who come to me in that situation what they’re good at, they answer in CV language. I’m really good with Excel. I can present PowerPoints in a meeting. And my advice is to try and get yourself out of that way of thinking and look below the surface.

What is the skill behind your ability to use Excel? Maybe it’s analytical skills or being a really organized person.

What is the skill behind being good at presentations? That’s communication, making sense of complex ideas, storytelling.

When you start thinking about the foundational skill beneath the things you’re doing day to day, it allows you to think much more broadly about where you could apply those things. Things end up being a lot more transferable than you might expect.

Subscribe to Alex’s Substack and follow his journey building Rumbo!

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TLDR: Having too many ideas is a filter problem, not a focus problem. By the end of this, you'll have a 4-step process for clearing the list and a Claude prompt you can use every time you hit this wall again .

At the start of this year, I dedicated my Q1 to a specific direction for my creator business. I spent months on it, hired externally, lost time and money, and eventually made the call to walk away. The moment I made the decision, I knew it was the right one.

And then I had the problem I seem to have every few years on a large scale, and every few months on a smaller scale:

…What now?

I had a running list of things I wanted to build: A course repackage. YouTube. Workshops. A community. A storytelling side practice. In-person events. Brand consulting. Eight directions after culling down the list… all of them real, all of them with a case for doing them. The possibilities felt endless, which was energizing and paralyzing in equal measure.

I was briefly frustrated, but I wasn’t panicking. I’d been here before when the stakes felt much higher. The blank slate feeling after leaving a job you’d worked toward for years. Knowing you want a new direction but having no idea what.

I’ve cycled through that more times than I can count from a career perspective. This was the same thing playing out on a smaller scale, inside my business.

So instead of just sitting with the spiral, I decided to systematize how I approach it.

If you’re building something outside your 9-5, or thinking about it, you probably know this feeling. You have more ideas than you know what to do with, and thinking about all of them at once makes it impossible to start any of them.

This framework is built specifically for figuring out what to build outside your job, but it adapts pretty easily to career pivots, life decisions, whatever version of “too many directions” you’re currently in.

1. Too many ideas is a good problem to have

If you feel like you have too many ideas, directions or pathways and can’t choose, that’s a good thing.

I mean that, not just in a “silver lining” way.

The alternative is much worse: brain fog, stagnation, malaise, zero pull in any direction. When the ideas keep coming, it means you’re genuinely multi-passionate and excited about each thing. That’s worth realizing before you try to solve it.

Some of the hardest conversations I have are with people who have the opposite problem — no list, no pull, nothing that feels like theirs. Just “I don’t know” or “I’m not sure”.

So a full list of things you want to do or build is a gift, even when it feels like a curse.

If you don’t have ideas you’re excited about, Step 1 and 2 of this process might help you too.

2. Being multi-passionate and being a maximizer aren’t the same thing

I wrote a piece earlier this year about the cost of keeping your options open — the maximizer tendency, common among people who came up in banking, consulting, and tech, to collect optionality instead of committing. That’s a real problem, and a very different one from having too many genuine interests.

A maximizer avoids committing because they’re afraid of choosing wrong. A multi-passionate person has multiple things that genuinely feel authentic and wants to build all of them. Committing harder and getting clarity on what you want solves the first. What solves the second is finding the thread that connects what you already have…and a way to sequence it.

3. Your ideas are related

In the moment, all your ideas feel distinct. But zoom out and the things you want to build are usually more related than they appear — they come from you, and you want them for a reason.

The thread is almost always there. It’s just hard to see from the inside.

When I left investment banking to work at a food delivery startup in Mexico City, those looked completely unrelated. The common thread was wanting to tackle something new and challenging where I’d actually feel the impact.

When I moved from a 1,000-person remote tech job to a 50-person startup last year, same thing — both let me work on go-to-market and learn what marketing looks like at different scales.

Even now, my day job (product marketing for a technical fintech startup) and building content for high-achieving people navigating nonlinear careers feel like completely different things on paper. But both come down to telling the story of a brand. One is a company’s. One is a person’s.

When I applied the same lens to my eight business directions, they stopped feeling like competing options. Several were just different expressions of the same thing, at different scales, or for slightly different audiences. The question quickly shifted from “which one?” to “which version” — and then “which one first?”

But in order to see how your ideas connect, you need a manifesto. Here’s my process for writing one and assessing your ideas against it.

The Process

You have to do Step 1 yourself. I wrote a Claude prompt to help you with 2-4!

Step 1: Get out of your head first.

When I feel stuck, my instinct is to keep pushing — keep analyzing, start something, anything. Wrong move (almost) every time.

What I’m actually looking for usually only surfacing when I step away: on a walk, in a sauna, at a random movie, at a dinner where work doesn’t come up. What I keep thinking about without trying or thinking about it from a new perspective. That tends to be more reliable signal than what I think I should be working on.

The more analog and orthogonal to your normal day, the better. A walk in an unexpected neighborhood. A bike ride. Time away from your phone. The goal is to let the right things rise without forcing them.

This is the hardest step because it looks like doing nothing. And it can be the hardest thing to do when you’re hell bent on “solving the problem” and this feels like…not doing that.

Step 2: Write your manifesto.

Once your head is clearer, write an anchoring statement for the next year or even just the next few months. This answers questions like: Who do you want to be? What do you want to learn and grow in? What kind of people do you want to build for? What kind of problems do you want to solve (and don’t want to solve)?

A page or a paragraph. The point is to have something to run your ideas against, so you’re not evaluating the list in a vacuum.

Step 3: Brain dump everything that’s on your brain.

Every direction, every half-formed idea, everything you’ve been talking yourself into or out of. Write them down, say them out loud, tell Claude. Don’t filter yet. Get everything on the table first.

Step 4: Assess and sequence.

Run each idea against your manifesto and your real constraints: time, energy, income needs, what you can actually test in the next 30 to 60 days. Surface the “shoulds” — the ideas that feel like you’re supposed to want them rather than ones you actually do — and cut them. What’s left gets prioritized into a goals document you can start acting on.

The Claude exercise

This past weekend, I ran through this four-phase process to assess my list of eight business directions and turned it into a Claude prompt that you can run for yourself.

HOW TO USE THIS: Copy everything below the line and paste it into a new Claude conversation. Claude will interview you through 5 phases and produce a Manifesto and a Goals Doc. Set aside 20–30 minutes. Answer honestly, not aspirationally. Ideally after you’ve done Step 1 (which Claude can’t do for you!)

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear path.

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230 of you signed up for the vibe coding event I co-hosted with my friend Yuqi from GMI Cloud at the Beacons office in NYC on Thursday!! (stay tuned for future events I’ll share here if you missed this one)

Now…sharing Sophia’s story with you!

Sophia Mullins spent nearly a decade in banking, PE, hedge funds, and VC. In the middle of it, she was diagnosed with Hashimoto’s thyroiditis at 25 after two years of specialists couldn’t figure out what was wrong. She overhauled her lifestyle, sent it into remission, and kept working in finance while building her wellness brand. She didn’t leave until she was ready to leave.

Sophia now runs Wall Street Wellness, a wellness consultancy that provides workshops, coaching, and advisory for companies and individuals in high-performance industries. She's building what she wished existed when she was the person on a lean PE team trying to figure out how to eat well, manage stress, and not burn out while working around the clock. She’s the person you call when you’ve tried the supplements, optimized your sleep score, and still running on fumes.

Sophia and I met through Instagram as fellow finance dropouts. So many of you have asked me how to take care of yourself when your job is high-pressure and nonstop, and honestly, I’ve been terrible at answering that question because I’m bad at it myself. Sophia has much better answers!

Whether you’re in a high-pressure job trying to figure out how to actually take care of yourself, or you’re thinking about building something on the side and wondering when the right time is to go all in, I think you’ll get a lot from this one.

Reverse engineering Wall Street from rural Ohio

Hannah: You grew up in rural Ohio, valedictorian, first-gen college student. When did Wall Street even become a concept for you?

Sophia: I honestly think I kind of reverse engineered it because it was not a concept in rural Ohio. If I told most of my older family members that I worked in banking, they would think I was putting the little plastic thing in the tube and sending it into a drive-through as a bank teller. It just was not an industry that really existed to them.

When I got to Ohio State, I connected with some upperclassmen who were heavily involved in investment banking and sales and trading. They came back from their internships super excited. And I had always known, I think from eight years old, I had a poster of New York City in my childhood bedroom. Rural was not really my vibe.

When I met those upperclassmen and saw how intellectually stimulated they were, the rigor and grit and obviously the prestige that came with Wall street, that was attractive to me. But also with my background, being a first-gen college student, not really having that safety net of going to a big city that’s obviously quite expensive, Wall Street was also a pretty surefire way to pay the bills and support myself as someone going there solo. I got really lucky connecting with the right people when I got to Ohio State to spark that initial interest.

How she built a wellness brand inside finance (without it becoming her whole identity)

Hannah: You started Wall Street Wellness as an Instagram page while you were transitioning from banking to PE. Were you already feeling the tension between work and health at that point?

Sophia: Pre-COVID, it was a little less common to talk about your well-being as a means to peak performance. I wasn’t really getting that side of myself expressed in my day-to-day working environment, so I took to the internet to connect with people. I knew other people had to also feel this way. I wanted to find that community, share what it was like to meal prep and go to Equinox while balancing 80-plus hour work weeks.

Hannah: Was wellness something your team knew about you? How did people respond?

Sophia: Earlier in my career, it was definitely not something I was front-footed about. If you got to spend time with me and we were talking about our personal lives, you’d pick up that I was doing a lot of wellness-based things with my limited free time. But as I got more senior, at my first PE firm and then hedge funds and VC, it became a bigger part of my personal brand. People started noticing behaviors. After you’re somewhere for six months or a year and someone sees you meal prepping or bringing your food in glass Tupperware, maybe they want to emulate those behaviors too.

A big thing I emphasize with my community is that you have to earn your chips first. You can’t show up to your first day of investment banking and say, hey, I’m the wellness person. But when you really show up, meet your responsibilities, exceed what’s expected of you, then you can be that positive example of: I’m here, I’m crushing it, I’m a top performer, and I’m taking care of myself. By the time I was VP and beyond, people would jokingly call me the Chief Wellness Officer. It was always perceived as a positive because they knew I was leading with my work ethic first.

The health crisis that changed how she thought about performance

Hannah: Tell me about the health symptoms. When did you first notice something was off?

Sophia: I started feeling off about a year into my banking experience. All of the lymph nodes in my neck were swollen to the size of marbles all the time. Really inconsistent energy levels, weight fluctuations, some weeks my skin would be super dry and then completely fine. Weird patterns across a lot of different ways you can monitor your health.

What’s so interesting about autoimmune conditions, especially how they manifest in women, is it’s really easy to point to them as just the symptoms of working in a high-stress environment. I was able to kind of shirk that off for a while. But then my lymph nodes had been swollen for six months at a time. At 24 to 25, this probably isn’t normal.

I started working with traditional medical practitioners at one of the highly rated medical systems in New York City. I had a lymphoma scare, where I had full body PET scan, all the tests, all the panels. About two years in, two doctors came into my examination room and said: “You’re just a medical mystery”. That was so unsettling.

Hannah: How did you manage those appointments while working full time?

Sophia: It was not easy. I was very open with my team. When you tell someone you need to go get a full body PET scan with radioactive sugar to rule out lymphoma, no one is going to stop you.

I was close with my VP at the time and pretty open with her because she’d had similar health struggles. She was like, do what you need to do. And going back to earning your chips, if I needed to be gone for two hours, I was really committed to: if I need to make a sacrifice for personal, it’s never going to affect what my team can expect from me.

The waitlists were also so long that it could take three months to get into the next specialist. It wasn’t like I was off the desk five times a month. It was more like once every three months, going on this trail of breadcrumbs to figure out what was wrong.

Hannah: What finally gave you answers?

Sophia: I was connected with a functional practitioner who looks at the body systemically, how all of our organ systems and functional systems are interconnected, because so much of the decisions we make in our lifestyle don’t just affect one part of us. All of our organs are connected in a symphony rather than being individual systems separate from one another, which is kind of how Western medicine looks at things.

Within one intake, a really extensive blood panel, and about three weeks total, she said: you very clearly have Hashimoto’s thyroiditis. Because you’re 25 and this hasn’t been manifesting for long, it would be very hard to catch by traditional measures. But because we look at tighter biomarker ranges, we can detect it earlier.

We did an extensive lifestyle overhaul. An intense cleanse and gut healing protocol, eating an anti-inflammatory diet and also got serious about stress management. Then a few months later, we retook all of my biomarkers that pointed to autoimmunity and my Hashimotos’ had gone into remission.

Why she stayed in finance after the diagnosis (and doesn’t regret a single year)

Hannah: After the diagnosis and the lifestyle shift, you didn’t leave finance. You went deeper with PE, hedge funds, VC. Why stay?

Sophia: These careers can be super fulfilling and intellectually stimulating if you actually feel well enough to enjoy the fruits of your labor. I knew I could stay in finance and probably retire at 50 with a very healthy bank account but always have that proverbial angel and devil on my shoulder asking, did you take that bet on yourself? Or I could leave, walk away from a lot of stability, and never have to question the what if. As I sat with that, the what if just got heavier and heavier.

Hannah: You’ve said you’re pro-corporate, which is kind of unusual coming from someone who eventually left. What do you mean by that?

Sophia: Respectfully, I don’t think the world needs another generalized millennial health coach. I think we need health professionals with unique backgrounds who can deeply relate to the people they’re serving. I get asked a lot: do you regret your time in finance? Absolutely not. It’s what enabled me to serve this group of people (high-achievers) so deeply, to be so niche that it actually moves the needle for them.

The difference between “green juice wellness” and actually feeling good

Hannah: There’s a version of wellness that high achievers get caught up in, the green juice, the red light mask, the powders. You push back on that pretty directly.

Sophia: I am guilty of this, so I can say it. A lot of high achievers, top performers, type A recovering perfectionists, can get caught up in performative wellness. Those things are all well and good, but if your fundamentals, like your movement, your nutrition, your mental health, your baseline resiliency and mental safety are out of whack, then you’re just putting band-aids on a much larger problem. It can feel like you’re checking your wellness box. But it’s a much deeper conversation than what supplements you can add or what new workout class to try.

I always tell people: it doesn’t matter if you’re drinking a green juice or eating a slice of pizza. If you’re in chronic fight or flight, neither is going to help. You really have to get to the root of mental safety and feeling good in your internal and external environments.

Hannah: So what do you tell someone who’s in a high-pressure environment with limited time and wants to do more than just the green juice?

Sophia: Find your one to three practices that are actually exciting to you for your mental and emotional health, and figure out the easiest next right decision you can make to open up that practice. It probably doesn’t look like doing breath work for an hour every day. Maybe it looks like blocking five minutes between Zooms to open an app and do it.

Small, consistent changes will actually move the needle versus going in super hot and setting up something unsustainable. The same goes for running, if you’re telling yourself you’re going to run a marathon and you start shooting for long runs on a Monday afternoon, you’re setting yourself up for failure. There’s a level of practicality and realism that actually sets people up for success.

Why she waited until she could build from abundance

Hannah: You left your PE role in July 2024 to do Wall Street Wellness full-time. What finally tipped it?

Sophia: This would not have worked if I’d left when I was 25. First and foremost, I wouldn’t have had the professional credibility that I carry with my corporate and individual clients. But also from a practical financial angle, I worked on Wall Street, had really stable, high-paying jobs, and lived below my means. I was kind of buying my flexibility. I call it building from a place of abundance. If I needed to replace my salary day one of Wall Street Wellness, I don’t think it would be as intentional or as thoughtful as it is now, because good things take time. I bought myself the flexibility to build this in the best way I could.

Hannah: You’ve described having a calling as a blessing and a curse. What do you mean?

Sophia: I was never the person who wanted to be an entrepreneur or start their own company. If anything, I was like, “Well, this doesn’t exist, so I guess I need to create it.” I want to bring this into the world, so I guess I’ll have to start a business. A lot of people want to start a business and then back into what that business will be. I was very much vice versa.

It has led to a lot of incredible opportunities because it’s just really obvious to who we interact with that this is so service-based and driven from a place of care and excitement. That’s not something you see very often. It’s become almost like a superpower for us.

Hannah: What’s been harder than you expected about going from VP in private equity to running your own thing?

Sophia: I came from finance thinking, oh, I’m so dynamic, I know what it’s like to wear 10 different hats per day. I didn’t know shit. It is so dynamic. Maybe you’re doing different types of tasks in a narrow corporate role, but here it’s like: I’m the CTO for an hour, then I need to go be the CAO, then the COO, then the CEO, then the chief salesperson.

I honestly just call entrepreneurship personal development boot camp. It requires you to not just figure out what you’re good at, which is sometimes easier, but get really honest about where your weak spots are. And either get better at those things, or outsource them, or hire someone with skill sets complementary to your own. If I hired another Sophia, we’d be duplicative. It’s been incredibly stimulating. I’ve grown professionally, obviously, but personally, it’s unmatched. I’ve really uncovered who I am.

Sophia’s 3 non-negotiables for daily wellness

Hannah: You now have the strictest boss you’ve ever had, yourself. What are your actual non-negotiables for your own wellness?

Sophia: I try to make it practical and realistic. If I came out of the gate every day with a 20-step morning routine, I would fail by 7:30am. So I narrow it down to what actually makes a difference for me.

Number one is eating an anti-inflammatory diet. Really mindful around gluten and dairy, trying to get 30 to 40 different plants on my plate every week, eating organic, high quality plant and animal proteins. I can notice a 30% difference in how I show up mentally and physically on a day after I’ve eaten really clean versus a day where I was more laissez-faire. That’s non-negotiable number one.

Number two is I walk outside every day. Rain, sleet, snow, shine, and I was in New York City for a long time before Miami. It is truly the biggest anchor for my mental health. Getting outside, getting fresh air, resetting my perspective that the world is so much bigger than my nuclear experience.

And number three is meditation. I personally am very easy to get wired and wound up, shoulders up to here, jaw cramping with tension. I am primed for that state. A lot of this work I’ve had to learn so deeply myself because that high-cortisol, high-tension state is like my nervous system’s comfort zone. But it’s not the comfort zone for any of my other bodily systems, so we had to figure that out.

Connect with Sophia on Instagram, Substack, and LinkedIn!

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart ambitious people forging nonlinear paths.

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I was at a wedding this weekend where several friends and acquaintances told me they had watched my recent Instagram videos about being “low status, high income.”

One even said it was giving her a lot to think about as she considered her next job.

This was a Wharton wedding. MBAs, consultants, bankers, people in tech - all high achieving, all who have spent their careers optimizing for prestige and equating status with wealth. When you’re that credentialed, status is hard to renounce. It’s your currency to be seen as peers with your social set, and until now it’s been your precursor to wealth.

So when even this crowd starts listening, I know the status game isn’t working.

The status-income matrix

The status-income matrix is a cross-section of how much society respects you versus how much you earn.

The x-axis is income, the y-axis is status. Two of the quadrants make sense. The other two don’t.

The two that make sense, because most of us have been trained to equate status with income:

• Low status, low income (fast food workers, cashiers, a lot of blue collar jobs)

• High status, high income (doctors, lawyers, bankers, engineers)

The two that don’t:

• High status, low income: nonprofit work, artists, journalists, teachers

• Low status, high income: solopreneurs, small business acquirers, people in crypto, content creators

These counterintuitive quadrants didn’t appear by accident. To understand how they got created and why the gap between status and income is growing, we have to first start with why we equate the two at all.

Seeking status as a proxy for wealth is human instinct

Naval Ravikant’s tweet storm “How to Get Rich” explains the historical reason humans value status:

“On an evolutionary basis, if you go back thousands of years, status is a much better predictor of survival than wealth is. You couldn’t have wealth before the farming age because you couldn’t store things. Hunter-gatherers carried everything on their backs. So, hunter-gatherers lived in entirely status based societies. Farmers started going to wealth-based societies. And the modern industrial economies are much more heavily wealth-based societies.”

So we’re wired for status first, wealth second. Once wealth started to matter, status became the signal we used to predict it. The Ivy degree, the brand-name employer, the right LinkedIn title. If you have those things, the assumption is the money follows. Sometimes it does, but sometimes you’re a journalist lunching on expense accounts with celebrities and wondering if you can make rent.

Institutions created high status, low income work

David Brooks published a piece in 1996 called The Tragedy of SID, or “status-income disequilibrium” - about what happens when the status signal and the wealth reality come apart. It’s the best explanation I’ve read for what created this quadrant.

His “sufferers” of SID include journalists, editors, news producers, and museum curators who are like “aristocrats” at work, lunching on expense accounts with the famous, but “like peasants” at home wondering if they can afford the bills. An army general might command 100,000 men but drive a Honda Accord.

Brooks traces this to “the proximity to wealth combined with the inability to match it,” but some of these fields also disequilibrate status and income by design. Teachers and nurses pay a “passion tax”. The tradition of starving artists receiving patronage from the wealthy stretches back centuries. UN internships are highly coveted but unpaid, available mainly to people who can already afford to be there.

The high status, low income job is a product of institutions that gave people status but kept the wealth for themselves.

Then the internet flipped that dynamic.

The rise of low status, high income work

A NY Mag piece that went around last month was a great example. They published the salaries of 60 New Yorkers, and some of the highest earners were jobs that barely existed, or weren’t that well paid, before the internet: ghostwriters, Substack writers, content creators. Ghostwriters and substackers out-earned bestselling authors. Exterminators out-earned nonprofit directors.

The internet has been the biggest innovation since Brooks wrote his article thirty years ago. Through the internet, more people no longer need institutions to vouch for their credibility or pay for traditional distribution of their work. Status becomes less necessary for building wealth.

And the people stuck in high status, low income jobs have a new out: the attention economy. Political aides can write tell-all memoirs. Laid-off journalists can launch Substacks. Often for much higher incomes than their prior high status institutions paid them.

The endpoint of this shift is when the originally low status jobs start getting perceived as high status.

That’s already happening. 68% of Gen Alpha want to be content creators. I had dozens of angry commenters on my videos saying I was ridiculous for calling content creation “low status”.

AI is accelerating all of this further, and we’re in the first innings.

You used to have to be a FAANG engineer to be a high status, high income software builder, but that’s breaking down with vibe coding. Physical jobs like plumbing and electrical work are starting to feel scarce in a way they haven’t in decades.

Status is, at its core, a proxy for scarcity, and the internet and AI are reshuffling what’s scarce.

The predicament of high status, high income

A lot of high achievers spent their careers in the top two quadrants. We’re conditioned to value the the degree, the fancy title, the feeling of importance. The unspoken assumption is that status and wealth are two sides of the same coin. By pursuing status, we in turn get wealth.

So the highest achieving people pursue the high status quadrants, which means more competition, more burnout, and a lot of people who stay stuck not because they’re happy or well compensated, but because the pull of status keeps them there.

As elite, large companies from Morgan Stanley to BCG to KPMG keep downsizing, this dynamic only intensifies as the same number of people compete for fewer and fewer jobs.

Why low status, high income jobs are the hidden opportunity

For the formerly high status, accepting low status is the underrated path to high income. A few reasons why:

First, less competition. A lot of low status roles have fewer qualified people going after them, which means more room to grow and less of a ceiling on what you can earn.

Second, your background commands a premium because it’s rare in that world. For example, an HVAC small business looking for someone to run finance and operations isn’t usually getting credentialed former bankers applying. When you do show up, you get paid for that scarcity. Your rigor, your pace, your analytical instincts add more value to industries where the bar is lower than what you’re used to.

Third, the income upside is often nonlinear in a way high status jobs aren’t. You might take a pay cut and a status cut at first. But you end up in industries with more room to grow than you’d have fighting for your share of a shrinking pool at the top because the opportunity is early and feels “beneath” the high status.

How to play the wealth game (not the status game)

If you’re ready to move to the low status, high income quadrant of work, wrote a post last year on 11 career paths where high achievers have an unfair advantage, many of which I now realize map to this quadrant. Not all of them are traditional “jobs” - much of the low status, high income world requires some degree of entrepreneurship.

A few principles for succeeding here:

1. Build and monetize a specific skill. This path is less about the title and more about what you’re uniquely good at. Naval writes about this a lot. The goal is a skill so specific that no one can really compete with you on it.

2. Create multiple income streams. High status job seekers tend to optimize for a prestigious base salary. But the average millionaire has multiple income streams. By diversifying how you earn, you stop tying your financial ceiling to a single job title.

3. Invest for the long run. Morgan Housel’s The Psychology of Money makes the case that some of the wealthiest people are not flashy spenders or high-status signallers. They make disciplined, boring investments that compound. The status game encourages spending. The wealth game rewards patience.

4. Look beyond the base salary. A lot of high-status job seekers only evaluate base pay. Commissions, bonuses, and opportunities to monetize your own expertise often don’t exist in elite jobs that require your full loyalty. Low status, high income paths tend to have more of these.

5. Use status as a tool, not a destination. It’s easier than ever to build a personal brand and manufacture credibility. That can give you proximity to opportunity and eventually to wealth, as long as you don’t confuse the signal for the goal.

As Naval Ravikant put it: “play the wealth game, not the status game”.

Status and wealth aren’t equal. This is just the beginning of the disequilibrium.

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart ambitious people forging nonlinear paths.

Short note this week! I want to share something I’ve been working on for you and why I built it.

Every week, someone in banking, consulting, or some other high-paying, prestigious-on-paper job asks me a version of the same question: “How do you actually leave?”

And I always want to say: you just quit. That’s how.

But I remember being so deep in it in banking that I couldn't picture what that would even look like. The “how” is much more complicated than it sounds.

I would make up my mind to leave after working 20 hours straight.

Then I would see my paycheck come in. A week would pass.

I would decide to quit after being berated for a missing footnote at 10pm. Then I would hesitate again because I couldn’t imagine making less money.

I would wait until the next paycheck and tell myself it would get easier. Or that I could just apply for an MBA and leave then. So on and so forth.

The whole time, I was trying to consume my way into clarity.

I thought that if I just found the right framework or heard the right story, I’d finally know what to do and have the courage to do it. That the money wouldn’t matter if I just had enough “clarity”.

I would feel briefly motivated after consuming the content, then go right back to work. Until the next month, the next bonus, the next performance review.

The thing I wish someone had told me then:

I was never going to get to solving the clarity problem until I proved to myself that leaving made financial sense.

I had a math problem to solve to first.

If you’re looking to leave a prestigious-on-paper, high-paying job that makes you feel like you have the proverbial golden handcuffs on, you have the same math problem to solve.

There are 3 numbers most people in your position never calculate:

Your true hourly rate. Not what’s on your offer letter — what you actually earn per hour. Real comp divided by real hours, with nights and weekends. Time you spend worrying and panicking about work. Mine in banking ended up being only $50 an hour.

Your replacement number. The income you’d actually need to maintain your life if you left. Not your salary — your real expenses once you strip out everything you spend because of the job. The apartment near the office, the dinners, the wardrobe. Most people find that it’s 40-60% of what they’re making now because so much of the status tax disappears with the job.

Your stagnation cost. What staying is already costing you — in skills you’re not building, positioning that gets harder to explain every year, experience in the thing you keep saying you’ll start when the timing is better. If you’ve already made up your mind to leave, every month you stay is a month you’re not compounding in the right direction.

None of these numbers are on your paycheck or offer letter. No one builds a spreadsheet for them.

But my “high-paying job” was costing me $120K a year.

My true hourly rate in banking was a fraction of what I made in my next job. After quitting, I saved and invested much more even though I made less. I started learning and growing in a field, where 5 years later, my unique skillset allowed me to build a secure 9-5 and 5-9.

Your numbers might be higher or lower than mine.

Come do the math with 800+ people next week.

I’m hosting a free live training on Tuesday, March 24 @ 7pm EST.

The Real Math Behind Your Golden Handcuffs (And What to Do About It)

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart ambitious people forging nonlinear paths.

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This week’s newsletter is a guest post from my friends Alex and Gerta, co-founders of YourNegotiations.com.

A year ago, Alex and I met after he commented on my Instagram post that went viral about learning the concept of BATNA in my Wharton negotiations class. Turns out, he also went to Wharton a few years before me, also worked as a product marketer in tech, and now runs YourNegotiations.com with Gerta, helping high-earning people in tech and startups (as well as founders) negotiate salaries and deals.

Alex and Gerta are both nonlinear career people. Alex was in the military before Wharton, and DJs on the side (he’s opened for the Chainsmokers!). Gerta has worked across startups and founded her own companies. And they run the whole thing together as a husband-wife team, which honestly feels closer to how work was done for most of human history, before the corporate era split everything into "work life" and "home life."

I learn a lot every week from their negotiations newsletter, so I asked them to write something specifically for you. A lot of you assume that changing careers means taking a pay cut or losing leverage. It doesn’t. Their advice breaks down how to think about negotiation when you’re in transition, and how not to sell yourself short.

Why career changers undervalue themselves

We’re in a peculiar job market. Yes it’s competitive, but it can be surprisingly unpredictable. For instance, several of our clients have received initial job offers at a lower title or level than at their last job, at comparable companies, but we’ve been able to help them negotiate compensation packages that are even higher than what they were making before. Old assumptions like “changing careers automatically means taking a step back financially” are no longer true.

We see these assumptions often held especially by people moving from finance, consulting, or big tech into new fields they’re genuinely excited about. But because they don’t check every box in the job description, they start the process already feeling like they should be flexible, grateful, or cautious about pushing too hard when negotiating their offers.

This mindset tends to show up early in the job search, sometimes without them even realizing it. And once they start interviewing, it impacts how negotiations unfold later.

The good news is that a career pivot doesn’t erase your leverage. But you do need to be thoughtful about how you carry yourself through the process.

Lay the groundwork early

A common misconception is that you start negotiating when the company extends an offer. However, you start shaping your future compensation far before that, sometimes as early as the online application itself when you’re asked for your preferred compensation (we wrote in this past newsletter about how to answer the salary question on the job application).

Here are a few things we strongly recommend that career changers keep in mind throughout the job search.

Be careful with early compensation questions

Sharing your preferred salary number will never help you, except in very rare edge cases.

Imagine that negotiations are like a game of cards, and the cards in your hand are your leverage. Your preferred salary number is a powerful card, and it’s hard to win the game by revealing it. The company has their own cards too, such as the “true max budget for this role” card, and they will never proactively reveal their cards either.

Note that in many US states, companies are mandated by law to share their salary range on job postings. These salary ranges are not truthful, as most companies follow the letter of the law but not the spirit of the law.

So if you share your number first, it will either:

• fall below the top of their budget. And they may agree to it, but you’ve now left money on the table, because the company knows that you’d be open to accepting less than what they’ve budgeted for.

• fall above the top of their budget. This introduces risk that they think you’re entitled, can’t afford you, or feel that you’re too far apart that you won’t be happy in the role even if you did accept. You’re a higher flight risk if you’re unhappy in the role, and companies want to hire people who will be there for the long term.

Some more reasons why sharing a number first is risky:

• Limits your bargaining power: If you share your number upfront, you may be limiting your bargaining power later in the negotiation process. Once you’ve disclosed your desired salary, the company may be less willing to negotiate higher than that figure.

• Lack of information: You may not have all the information you need to make an informed decision about your desired compensation until later in the interview process. By sharing a number upfront, you risk locking yourself into an end result based on incomplete information.

• Perception of being inflexible: If you share a number upfront, especially if it ends up being far above their budget, you may be perceived as inflexible or difficult to work with. This might not be the case, but perception can be just as important as reality in the hiring and negotiation process.

• Different compensation structures: Different companies may have different compensation structures, including stock options versus shares, vesting periods and cliffs, stock buyback windows, various bonus types, commission-based pay, and more. Sharing a number doesn’t necessarily capture these complexities, so you may be missing opportunities later to arrive at creative solutions that will make the offer worth accepting.

On that note, sharing a range is very similar to sharing a number, because when you share a range, you’re implying the bottom of your range is an acceptable amount to you. So we recommend not sharing a range either.

If you’re asked for a number or range early on, tactfully deflect sharing it and instead say something like: “Thank you for asking! I’m currently focused on exploring that this is a mutually good fit. I’m confident we can align on compensation.”

There are many ways you can phrase deflections, and much of it depends on your unique circumstances, whether you’re in between jobs or currently working, the company culture, the demeanor of the recruiter, if you were referred, whether you have an existing relationship with the hiring manager or someone from the team, and more. You can book a free call with us to get specific tips for your situation.

Avoid oversharing in general

What makes someone a great employee in most jobs nowadays but also makes them bad at negotiations? Oversharing.

It’s virtually guaranteed that you’ll get pushback from the company whenever you refrain from sharing something.

That includes your current or past compensation, the details of other offers you’ve received, or other opportunities you’re considering. Note: it’s illegal in many US states for employers to ask for your salary history.

Being transparent can feel collaborative, but it often gives away information that’s hard to take back. We’ve written before here about how overcommunication is a common trait shared by high performers but bad negotiators, and what to do instead.

Negotiating well signals that you’d make a strong hire

Being overly transparent comes at another cost. You may think you’re being trusting and collaborative, but it can also signal that you cave under pressure, you may be too people pleasing, you may not know how and when to be strategic, and you may not have the skills needed to handle challenging conversations, all of which are important traits companies look for when hiring.

Imagine that you accepted the first offer a company made you without negotiating. It could get the hiring manager thinking, “This candidate just said yes to the first offer. Is this how they’re going to handle their work with cross-functional teams across the company, business partners, external vendors, investors?”

Many years ago, Gerta negotiated her job offer against a tough and driven hiring manager. Once Gerta started the job, that manager put her in charge of the team’s most important and highest-priority projects, telling Gerta, “I remember how you negotiated your offer, so I trust you to lead this work.”

Negotiating your offer well doesn’t happen in a vacuum during the job search. It also reflects how your manager and team will perceive you in the job, as someone with competence and strong business acumen.

Always show excitement for the role

You can never show too much enthusiasm. We’ve sometimes been asked, “If I show too much enthusiasm, doesn’t that make me seem desperate for the job and thus lose leverage?” or “I have multiple offers, isn’t it better to play hard to get and pit the companies against each other when negotiating?”

No. Companies want to hire people who will be excited to work there. That means you’ll be motivated in the job, onramp quickly, and be a pleasant co-worker to work alongside. If you’re playing it cool, a company may interpret that as you not being fully committed, that you’re using them as leverage for another opportunity that excites you more, or that you won’t be a good culture fit.

Showing enthusiasm is even more important in today’s tough job market. Competition for roles is especially tough, and many jobs are getting hundreds, if not thousands, of applicants. By the time a company has whittled down to a final list of candidates for a particular role, every candidate on that list more than meets the qualifications or technical skills required for the job. So what’s the differentiator that has them choose someone over others? At that point, it often comes down to whether they think they’ll like working with you.

On mindset: you have more leverage than you may think

Unfortunately, the norms around the recruiting and negotiation process naturally favor employers because job applicants assume that the companies hold all the cards. This can feel truer if you’re switching career tracks and feel brand new to the industry.

But remember, you as a competitive candidate have leverage too with your experience, qualifications, and optionality (i.e. you should always apply to multiple roles when job searching; never just one at a time).

Negotiating may feel risky, but reframing the process for yourself can have you show up in all your conversations from a more empowered state of mind. You’re not asking a company for favors, but you’re exploring together to find a win-win deal for all parties involved.

For more about how to get into the negotiation mindset, we covered this in-depth in this past newsletter.

More resources

Changing careers can feel like you’re starting over, but don’t let this move convince you that you don’t have leverage.

For more tips and resources if you’re job searching:

• Transition Doc - If you’re leaving your job soon, download our free template to organize and handoff your work to your backfills (your coworkers will thank you!)

• Book a free call for tailored job search and negotiation advice for your situation

• Subscribe to our weekly negotiation newsletter

• Download our free worksheet to keep handy during your job interviews

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• Bits in, bits out

• I’ll say it one more f*cking time: Be so delusional reality has no choice but to bend to your vision

• How to start a one-person business in 2026 (things changed)

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart ambitious people forging nonlinear paths.

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Julia Lynch Eckstein is the kind of person who, if you told her you were thinking about leaving consulting to do something that doesn’t map cleanly to a job title, would pull out her phone and connect you with three people before you finished your thought.

Julia and I met through following each other’s content on Instagram, and she was one of the first people who introduced me to the idea of a portfolio career.

She spent years in strategy consulting while building a career and personal branding strategy practice and a content platform with 160K+ followers. She left her consulting job in August 2024 to go all-in on her portfolio career.

Funny enough, we’re both (unofficially and officially) part of the Wharton community. Julia’s husband graduated with his MBA from Wharton a year ahead of me. Julia (who was very much part of Wharton student community during her two years in Philly) and I immediately bonded over how the cut-and-dry “MBA —> high-earning career success” path no longer exists. We both strongly believe that MBA programs need to catch up to the market—and not only teach students how to get a job, but build a portfolio career.

We got into how her career transition materialized, why she doesn’t call herself a coach, her concept of “relationship currency,” and what high achievers get wrong when they’re stuck.

If you’re thinking about building something on the side, curious about a portfolio career, looking to pivot, or just want to get better at networking — I think you’ll get a lot out of our conversation.

Following the herd (and realizing it wasn’t working)

Hannah: You went to NYU and then Kellogg, and then into strategy consulting. What were you initially looking for when you jumped into that path?

Julia: I was following the herd, honestly. I graduated from NYU and worked abroad in Asia for a year. I come from a family of lawyers. I’m actually the only non-lawyer in my family. The expected path was that Julia’s going to work abroad for a year and then go to law school.

I took the LSAT, scored well, but I just thought the content was so boring. I’ve always been really entrepreneurial, so I decided to go to business school and become a management consultant. You get so much business experience as a consultant, and it’s a great way to learn about businesses.

I ended up doing a Master of Management program at Kellogg. For any undergrad who’s not sure what they want to do and has a liberal arts degree, I highly recommend a program like this. The Kellogg program is now only open to current Northwestern students, but there are similar programs at Duke Fuqua and Michigan Ross. My undergrad was media, culture, and communication, so I needed some of that foundational business acumen. Coming out of the program, people either took the consulting path or the investment banking path. I figured slide decks were more aligned to my skillset than sitting in front of Excel all day. I never took calculus. Math was not my thing.

But from the beginning, consulting wasn’t aligned with my skill set. I felt like a paper pusher. I always felt like my strengths were really in brand strategy, people, communication. I was always the person people went to for career advice. Even when I was living in Asia, I was doing a little bit of that work with people who were much more senior to me.

What the pandemic changed

Hannah: When did you first start thinking about doing something beyond your day job?

Julia: During the pandemic, I was living in my parents’ basement like everyone. I was 27, single, coming home from work, watching Bravo, going on horrible dates. I just thought, I don’t think this is what your 20s should be like. I think I have more to give, and I don’t think consulting is for me.

So I started sharing on social media. Things I liked. I’m a big reader, I love listening to podcasts. I didn’t show my face at first, and I was just speaking to things I enjoyed. I had maybe 200 followers.

Then Covid hit and I said, this is an opportunity to give back. I was only working about 20 hours a week in consulting, so I had the bandwidth. I put it out to my 200 followers: if you’ve been laid off due to Covid, I will help you. I’ll do your resume. I’ll connect you to recruiters I know.

That turned into recruiting 65 volunteers. We were on national news. And then people started coming to me saying, “You’re really good at this. I’ve worked with executive coaches and career coaches before, but I want to pay you.”

It really turned from an act of service into a business, which is not the typical trajectory.

Balancing the day job with the thing you’re actually excited about

Hannah: There was quite a gap between when you started doing this on the side and when you went full time. How did you balance that?

Julia: Because I had a full-time job, there were natural limits on my time. But knowing there was something greater ahead of me, and feeling like day to day at my day job I was just kind of not over-performing, I got really excited about what I was doing for individuals and what I was sharing on social media.

I also felt that in consulting, I was no longer learning. And I think that’s the point where a lot of people feel like something needs to change. My advice would be: don’t let that feeling of “I’m not learning” persist for a long time, because your career is only so long and things accelerate very quickly. It’s easy to get trapped in patterns where you’re just clocking in and clocking out.

I’m not a parent, and I know you’re not either. I personally feel like these precious years before you have kids, you should be going to bed exhausted. I’m in this data collection year, speaking to people who run businesses or are really successful women in my network who do have kids. And you have natural limits on your time once that happens. So if you’re reading this and you don’t have kids, this should be your time to be exploring, doing, thinking before you have those limits.

Hannah: I really like that perspective. It’s stepping out from your day-to-day and looking at it with a different lens.

Building the portfolio career (and not picking one lane)

Hannah: You started posting on social media initially to feed your curiosity and share things you were learning. Then during Covid it evolved to career coaching. Now you also do personal brand strategy. Did all of those things develop naturally?

Julia: All the things I do dovetail really naturally together. Each pillar of my portfolio career informs the others and makes me better at each one.

Instagram and social media, yes, it’s a way for me to reach people I might not ever interact with one to one. But it’s also allowed me to build a network and friendships with people who I’m naturally aligned with and intellectually curious about. I was really looking for that when I started posting, because all of my friends were in relationships and my social life changed overnight. I almost created my own friendship circle from Instagram.

I have people I’ve met through Instagram that I’ve never met in person, who I consider dear friends, who we’ve helped each other immensely with our businesses. So if someone is looking to start a content presence, I’d say it’s not only for the views. It’s for the depth of relationships you’re going to get out of it. Relationship currency is core to everything I do, and it’s something people don’t talk about enough as a creator.

Your network is your job insurance

Hannah: I love that term, relationship currency. How do you define that?

Julia: I really believe your network is your job insurance. We have medical insurance, right? If I got hit by a car tomorrow, I’d have the fallback that my hospital bills would be covered. But a lot of people don’t think about their network the same way. It’s just, “Oh, this is something I have to do if I’m laid off or want to change careers.”

It should always be an undercurrent to what you’re doing. Layoffs are uncertain. AI is changing the way we work. Thinking of relationship currency, I really think of it as: if my business went away tomorrow, God forbid, would I have relationships and people who trust my expertise, where I could start from zero? Whether you’re an entrepreneur or in corporate, that same mindset should apply.

Letting go of prestige

Hannah: You went from management consultant to career coach, personal branding, content creation. Consulting is something a lot of people really aspire to. How did you step out of that prestigious position?

Julia: It was something I really struggled with. Even meeting some of my husband’s Wharton classmates, many of them didn’t know I had this business. Because those spaces are very much about your McKinsey, your Bain, your BCG. Those are the measures.

But ultimately I had to get over it and realize I was bored. I was never going to be a top 1% management consultant. Your career should be about optimizing for your God-given natural abilities. Mine are not sitting in front of decks, moving something 1 millimeter to the right, sitting in front of Excel.

A lot of people are wedded to “this is the path that should make me a lot of money.” But if you take a step back and think about what skills you have, you might not have that title, but you’re going to have more financial stability, more money, everything. A lot of career stuff is about perception. “I don’t want to move to this startup because I’ve had five amazing brands on my resume.” Well, ultimately, you’re the architect of that. If you want to live a specific life, you kind of have to let go of what people think of you.

I’ve talked to partners in consulting and managing directors in investment banking who wish they took risks earlier. That small AI startup, a completely different industry, entrepreneurship through acquisition. But they didn’t because they were wedded to that perception.

Not your typical career coach

Hannah: What drew you to career coaching specifically? I think something interesting about your branding is that you’re a very different type of coach - most people in consulting and finance don’t have the best perception of career coaches. How did you think about that when you started?

Julia: I don’t even like calling myself a coach because it’s kind of schlocky. It’s the same kind of label as “recruiter.” What I find in the career coaching space is that a lot of coaches operate more like therapists. My mom is a therapist, and of course there is a time and place for that. But there’s a missing piece: who are the individuals who can understand your skill set, map out your life goals, figure out where you operate in the top 1%, and help you activate your own network and social capital?

I call myself a career and personal brand strategist, because when you’re thinking about the next stage of your career, your personal brand is embedded in that.

My approach to clients is networking and storytelling. I won’t take on a client if I’m not comfortable introducing them to someone in my network and saying, “Hannah, this individual is going to add value to you. This person would be a value add for the role your startup is hiring for.” That’s very different from coaches who work with people in isolation.

A lot of my clients have gotten jobs through connections I’ve made for them. I don’t sell myself as a recruiter. But I say that when you exit our relationship, you’re not only going to have a stronger approach to networking and storytelling, you’re going to have core relationships you can bring into this next chapter. No one else really takes that approach.

What people get wrong about networking

Hannah: For a lot of people, when they hear networking, they think it’s gross and transactional. What do you think they’re getting wrong?

Julia: Networking is not always going to be an even value exchange. You might be a student trying to network with someone three levels senior. What’s a piece of value you can bring? Look at their LinkedIn. Maybe they’re into sports. Maybe they’re a restaurant fan. Recommend a restaurant you went to. Say, “I just graduated from college. Are you doing any research around Gen Z?” There are creative ways to position yourself as someone of value versus just thinking, “I’m not on the same plane as this person, so I’m intimidated.”

The other thing is follow-up and follow-through. I’ve talked to many senior leaders who have this “great little black book” but only reach out when they need something. They’re not making those relationships personal. They’re not following up and adding value at every turn.

If you can give something without the expectation of receiving, that’s when things come back to you. That’s how your career really grows.

On the 2026 job market and being “risk on”

Hannah: You work with a lot of high-achieving people. What would you say is the most important thing people need to understand about the job market right now?

Julia: Number one: be visible. I’m not saying become a content creator. But post on LinkedIn once a month. Go to a networking event. Meet individuals. Get some fresh blood in your life. Foster relationships externally as well as internally.

Also, the levers of wealth building are changing. The traditional consulting and investment banking paths, those are still paths to wealth, but have those salaries kept up with inflation? Absolutely not. So think about where people are earning a lot and whether you’re okay taking a risk.

In your career, with great risk comes great reward. If someone is 27, doesn’t have kids, and wants to make a big career shift, that’s the time to take a bet on a startup where they can really supercharge their skill set. That’s the time to move to a different city or do a boot camp in a new industry with growth potential.

Think of your career like an investment portfolio. At our age, we’re risk on. When we’re 60, we’re going to have the most boring portfolio of all time. If you think of yourself as a product and align your career the same way, you’re going to achieve success.

If you’re stuck and not sure what’s next

Hannah: For someone who’s a high achiever, willing to be risk on, but feeling stuck and not even sure what that next step would be, what would be your advice?

Julia: Do an accounting of your expenses. What does it take you to live? What is your lowest operating cost?

Then think about who in your life is thriving. Approach them and be vulnerable about your career ambitions and how they got to where they are. Applying for jobs is one thing, but collecting data from people who already trust you and know your skill set is ultimately going to open doors. Network with your close circle first, then expand to people outside of that who are willing to take a bet on your social currency and have a conversation with you.

Subscribe to Career Confessionals

If you’re curious about high-paying, non-conventional careers, Julia recently launched a Substack series called Career Confessionals. It spotlights professionals under 45 earning $250K+ in niche careers…and gives you a roadmap to replicate that same path for yourself. It is one of the few Substacks I pay for (and it’s worth every penny of the $5/month). I LOVED the first one about a meth addict turned millionaire 👀

Connect with Julia on Instagram, TikTok and LinkedIn!

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• How to build a profitable personal brand in 30 days

• The Brand Age (Paul Graham)

• Labor market impacts of AI (Anthropic)

• Forum: B2B startup accelerator for idea-stage founders

• ❓Take my career exit quiz

• cool jobs for ambitious nonlinears (updated ~weekly)

• my resources

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Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart ambitious people with unconventional paths.

📣📣 TAKE MY CAREER EXIT QUIZ 📣📣

If you've been reading this newsletter for a while (or even if you just found me), there's a good chance you're thinking about making a career move. After talking to hundreds of you about your career transitions, I started noticing the same 4 patterns. I turned it into a 2-minute quiz that tells you your exit type and what to actually do next.

What's your exit type? →

I posted a video this week that resonated with a lot of people - articles for people figuring out what’s next in their career, so I wanted to make sure you didn’t miss them.

I think these resonated because they’re the kind of smart career advice that feels like a rare find for those of us who are ambitious but want to succeed on our own terms, so “normal” career advice doesn’t usually fit the bill. Some of these articles feel tech and startup coded because of who they come from (the founders of YC and a16z), but I think the ideas are bigger than that and applicable to anyone with a nonlinear, portfolio career.

These are 5 articles that shaped how I think about my career post banking and tech - here’s a quick overview of each, who each one is for, and what I took away.

I’m curious: have you read any of these? Which ones resonated most? I’m always looking for stuff like this, so if you have articles or books that helped you figure out your own path, send them my way.

1. “How to Do What You Love” by Paul Graham

Paul Graham is the founder of Y Combinator, and this essay is one of the most-read things he’s ever written. It’s about why smart people end up in careers they don’t actually enjoy, and what to do about it.

The part that changed my thinking was what he says about prestige. When I was in banking, I couldn’t articulate why I’d chosen it beyond “it was the hardest thing to get into.” Graham puts words to that:

“Prestige is the opinion of the rest of the world. Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.”

That line is what made me realize I chose my career for the wrong reason. I didn’t love banking. I loved that other people were impressed by it.

Who this is for: If you picked your job because it was competitive to get, or because it looks good on Linkedin (formerly guilty of both…), read this.

2. “Hell Yeah or No” by Derek Sivers

This one is short and it’s a framework more than an essay. The idea: if you’re not saying “hell yeah!” to an opportunity, say no.

This is useful because sometimes we have an easier time knowing what we don’t want than what we do. And if you’re someone who says yes to everything because you’re afraid of missing out on the right thing, this reframes the problem.

Who this is for: The person with 14 tabs open, three job applications half-finished, and a Google Doc of unfinished side project ideas. If you’re spread thin and can’t figure out what to focus on, start here.

3. “How to Pick a Career (That Actually Fits You)” by Tim Urban

This is a long one (it’s Wait But Why, so expect stick figures and 10,000 words), but it’s the most thorough thing I’ve read on why career decisions feel so paralyzing.

Tim Urban has this concept called the Yearning Octopus. The idea is that you have all these different parts of yourself that want different things at the same time. Your ego wants prestige. Your lifestyle tentacle wants comfort. Your social tentacle wants your family’s approval. Your practical tentacle wants financial security. And they’re all pulling in different directions.

The key insight is that you have to untangle which yearnings are actually yours and which ones belong to someone else - your parents, your peers, society. Most people never do that. They just follow whichever tentacle is loudest.

Who this is for: If you feel pulled in ten directions and can’t make a decision, this will help you understand why. It’s especially good for people early in a career transition who feel paralyzed.

4. “Make Your Work Your Calling” by Arthur C. Brooks

This feels like the most pragmatic one on the list, and it’s for a different stage than the others. The articles above are about figuring out what you want. This one is about what to do when you already know your current job isn’t it, but you can’t leave yet.

Brooks’ argument is that you don’t need to wait for your calling to find you. You can turn whatever work you’re doing into your calling by focusing on what’s intrinsically interesting about it and finding ways to serve the people around you.

I know that sounds a little idealistic, but I actually think it’s a good bridge for people who feel stuck. You don’t have to love your job to get something real out of it while you figure out your next move.

Who this is for: If you’re not ready to quit but need to stop dreading Monday mornings while you plan your exit.

5. “Pmarca Guide to Career Planning” by Marc Andreessen

I saved my favorite for last. Marc Andreessen is the co-founder of a16z and one of the most influential people in tech.

His core advice: don’t plan your career.

“Do not plan your career. Instead of planning your career, focus on developing skills and pursuing opportunities. I believe you should look at your career as a portfolio of jobs/roles/opportunities.”

This resonates with me because it’s basically how my career has worked, even though I didn’t plan it that way. I went from banking to tech to startups to business school to content creation, and none of that was on a five-year plan. Each move made sense at the time because I was following skills and opportunities, not a predetermined path.

This is just the first part of Marc’s career advice - the other parts delve into more tactical advice like how to pick degrees and job functions. Great read all around.

Who this is for: Anyone who’s driven and talented but feels behind because their career doesn’t look like a clean ladder.

Reads, Ideas, Tools

• 2028 Global Intelligence Crisis - the infamous viral “stock market fanfiction” this week

• Unoptimized - love these mini essays from Quartermile!

Jobs

• Associate, GTM Finance & Operations – Ramp (Fintech, Late Stage, Hybrid - NY)

• Operations Associate – Initialized (Venture Capital, Seed Stage, Hybrid - SF)

• Growth Manager – Pond (Crypto, Startup, SF)

• Chief of Staff – Walker Hamill (Venture Capital, Boutique, UK)

• Manager or Sr. Manager of Strategic Finance – GridCARE (Infrastructure & Energy, Series B+, Hybrid - CA)

• AI Builders – Wealthsimple (Fintech, Growth Stage, Remote)

• Operations Manager (Finance) – Revolut (Fintech, Late Stage, Remote)

• Senior Manager, Strategic Operations – 1Password (SaaS, Late Stage, Remote)

• Chief of Staff – Route 66 Ventures (Healthtech, Early Stage, Remote)

• Engagement Associate - Partner Engagements – Aleph (Fintech, Early Stage, Remote)

• Partner Strategy & Operations – OpenAI (AI, Frontier Tech, Hybrid - SF)

• Senior Associate, Innovation & New Bets - Strategy & Operations – DoorDash (SaaS, Public Company, Remote)

Resources

• ❓Take my career exit quiz

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• my resources

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