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

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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

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• 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.

Read more

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.

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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)

Let’s see what numbers look like for you.

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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

• GTM Engineer – Casper Studios (AI, Bootstrapped, Remote)

• Faculty Lead & Learning Engineer – Outsmart (Education, Early Stage, LA/SF/UT)

• Consultant - AI and Semiconductors – SemiAnalysis (AI, Growth Stage, Remote)

• Finance and Business Operations Manager – OpenRouter (Infrastructure, Growth Stage, Remote)

• Chief of Staff – Stealth (Life Sciences, Late Stage, Remote)

• Network Engagement Specialist, Harvard Innovation Labs – Harvard University (Education, Public, Hybrid - MA)

• Strategy & Growth Leader – Stealth (Pet Health & Nutrition, Series B, Hybrid - NY)

• Chief of Staff – Strange Ventures (Deep Tech, Startup, SF)

• GTM Manager (Customer Success) – Axle (Finance, Series B, NY)

• GTM Strategy and Ops – Mercor (AI, Series A, Hybrid - SF)

• Legal Operations Lead – Medibank (Insurance, Public, VIC)

• 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)

• ❓Take my career exit quiz

• my resources

Find me on: Instagram, Linkedin, Tiktok, Youtube

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!

• Director, Operations Strategy – Create (Consumer Health & Wellness, Startup, NY)

• BizOps – Salient (Fintech, Series A, SF)

• Analyst/Associate – Equal Ventures (Venture Capital, Early Stage, NY)

• Content Engineer – Virio (Technology, Startup, SF)

• Senior Strategy & Operations Associate, Growth Strategy – Lyra Health (Mental Health, Growth Stage, Remote)

• Chief of Staff – Superpower (Healthtech, Series A, SF)

• Strategy Lead, Global Membership – Uber One (Rideshare, Public Company, Hybrid - NY/SF)

• Chief of Staff – Stealth (Startup, NYC/Remote)

• Operations – Relay (Fintech, Growth Stage)

• Founding Growth Associate – Plot (Software, Seed Stage, NY)

• Product Finance & Strategy Manager – Nextdoor (Social Network, Public Company, Hybrid - SF)

• Strategy & Operations, Enterprise Business Partner – Anthropic (AI, Late Stage, Hybrid - SF/NY)

• Chief of Staff to CEO – Ashaki (Fashion & Media, Startup, SF)

• 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

Find me on: Instagram, Linkedin, Tiktok, Youtube

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

• your 30 day side project plan

• my resources

Find me on: Instagram, Linkedin, Tiktok, Youtube

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 Was a Harvard Grad and Goldman PM. Now I’m Unemployed and in the Woods. How Did I Get Here?”

This was the title of the viral YouTube video that introduced me to Yuqi Hou. We have a lot in common — left prestigious jobs, started creating content, and building in public. I’ve been following her ever since so asking her to share more her story and how she “figured it out” felt like a long time coming.

Yuqi spent five years at Goldman, moved to London as a Senior PM at a unicorn startup, got laid off, and grew a YouTube channel to almost 10,000 subscribers while figuring out what she actually wanted. She just moved to San Francisco for a developer community role at an AI startup.

We talked about how she went from optimizing for prestige to building a career on her own terms, how she leaned into creative pursuits like content creation and novel writing, and what 20 months without a job taught her.

She shared what her dad used to tell her, “Why are you so stressed out at work? If you don’t like it, quit. You can always find another job.” It took getting laid off, a 20-month gap year, and moving across two countries before she finally believed him.

Getting into Goldman (and then wondering what’s next)

Hannah: You started at Goldman right out of Harvard. What were you looking for in that first job?

Yuqi: Prestige, status, and to be amongst my peers. A lot of people I admired in college were getting internships at Goldman. For me, it was a way to feel like I was at a peer level with them. If I wanted to come and chat with them and feel like I’m at the same level, I felt like I needed to have that internship. And it’s Goldman. You kind of wonder what it’s like really on the inside. If I had a chance to find out, I wanted to find out.

Hannah: You started as a program manager, then moved into developer advocacy and product management. How did those shifts happen?

Yuqi: I was very lucky. My first year I had an internship in UX, then I met a bunch of PMs that summer. When I came back full time in PM, my manager left, so I had this new manager who was doing something totally new. It was just me and him. He spun up a data business and needed somebody to do anything and everything, which meant I was doing product, developer advocacy, all of it. I got to try out a lot of different roles.

My advice to everyone is: if you can join a startup within a big company, that gives you a lot of flexibility to try things you might not normally get to, because you have some stability but also some room to experiment.

Hannah: When did the “prestige halo” fall away?

Yuqi: Pretty early on. Once I got there, I realized I hadn’t thought about what would happen beyond Goldman. It was like, this is the pinnacle, so I will stick and be stable. I didn’t even think there were other levels beyond where I was.

I got promoted early, got my bonus, and the question of “what’s next” just kept coming up. I tried having a life outside work, and that just made the difference between work and what I found interesting even more apparent. I wanted to bridge that gap.

Hannah: How so?

Yuqi: After work, I started writing a novel. And I realized I was basically two people. Nine-to-five Yuqi and then creative Yuqi outside of work. I just think life is easier when things flow into each other. Like right now, I go to tech events and get ideas about events I want to put on, which helps me in my day job. If I’m writing outside of work, that helps me communicate better at work. Everything compounds.

Whereas if you’re doing completely different things outside of work than you do at work, you’re not compounding anything.

The startup, London, and what broke

Hannah: What made you leave Goldman for Jellysmack?

Yuqi: Jellysmack was one of those big, unexpected moves. I found it through Indeed. I didn’t know anything about the company. I was just blind applying to a lot of places because after six years at Goldman, I’d lost a lot of confidence in my ability to do something outside of it. When you’re somewhere that long, you almost wonder, is this the best I can do?

Jellysmack was one of the first companies I applied to. The interview process was quick, I liked all the people, and the most important thing was it was creative. Their users were all YouTubers. I was thinking about how to build products for YouTubers to make more videos, make them faster. That really led to wanting to do YouTube myself.

Plus, the team was split across the US, London, and Paris. I really wanted to travel, and I thought this job would help me get to London and Paris. Which it did.

Hannah: You moved to London for this role. Was that planned from the start?

Yuqi: Not really. I threw out “I’m willing to relocate” as a Hail Mary because I was getting laid off at the time. During the layoff meeting, it was my HR and my head of product in a room, and I got the news, and I said I’m willing to relocate. Two weeks later they said, okay, let’s do it. I thought I was going to Paris. They said London. I took it because when else am I going to have the chance to live abroad?

I actually learned from this that I enjoy building a social circle from the ground up. I started from zero in a new country. One of my first videos was “How to Make Friends in London: 9 Places to Find Friends.”

The gap year (that turned into 20 months)

Hannah: When you got laid off from Jellysmack, what did you think the time off would look like?

Yuqi: I thought I would do something like 12 apps in 12 months. Ship something every month and it would tell me if this is the direction I can go. But instead I spent so much time with friends and family. I went on a month-long trip to China with my family because I decided family is super important. I wanted to reconnect with my dad’s side of the family. That was worthwhile because now I have the sense that I’ll go to China every couple of years and stay better in touch with extended family.

Hannah: How long did the gap end up being?

Yuqi: Twenty months. Eighteen months of that was the true gap, and two months was intense job search. I was lightly job searching at the beginning because in London you need a work visa, so that was always in the back of my head. I was very conflicted about whether I should commit to the UK or come back to the US.

Hannah: What did the gap year teach you that you couldn’t have learned while working?

Yuqi: The confidence of knowing I’m going to be okay. I spent 20 months figuring it out, and now that I have a job, I realize this thing that was very scary to me at the time, taking a career break, I wasn’t even going to allow myself to do it. The only reason I did was because I got laid off. I wouldn’t have quit on my own because I had no confidence that I could figure it out or even get a job afterwards.

My dad used to always say to me, “Why are you so stressed out at work? If you don’t like it, quit. You can always find another job.” Very chill, very grounded. I just didn’t believe it, even though I knew logically I could probably get another job. But now I feel that confidence. I get what my dad was saying.

Hannah: For people worried about the financial side of taking time off, what do you know now that you didn’t then?

Yuqi: I didn’t know that I could take even more risk. I was really worried about burning through rent money, but now I know so much more about how much I can stretch my savings. I didn’t calculate my runway before I started. I only got on top of my personal finance because I started making YouTube videos about it and had public accountability to give people updates on my real-time experiment.

YouTube and building in public

Hannah: How did you go from wanting to ship 12 apps to making that first YouTube video?

Yuqi: YouTube was something I started probably one or two months before I got laid off. I was building an AI assistant for content creators and felt like I’d get more understanding if I just did it myself. So I made my first video. Didn’t do anything. Two months later, got laid off, and I thought, I have no excuse now.

I started documenting what I was making, put it out, and realized making products successful takes ongoing effort. So you know what’s easier? Vlogging. That was the thing I could keep consistent at more than building apps.

Hannah: You had a video blow up. What was that experience like?

Yuqi: I felt so much more self-conscious after. I was trying to maintain consistency between videos, and whatever I talked about needed to come on the same topic so people understood where I was going.

Initially I was making videos about how to find your social circle, my hobbies, trying tennis, travel, surfing. I stayed away from sharing a personal story for a really long time. Then one of my early commenters asked, “Can you tell me why you started this gap year? You’ve talked about it but never shared why.” That’s when I went into my history. That was the video that blew up.

I’m so glad I started out with the random videos, though, because I had proof that I was more than prestige and names. I wasn’t just banking on brand names.

Hannah: How did creating in public change how you thought about what you wanted to do next?

Yuqi: I’d consider myself somebody who builds in public and shares in public more than a content creator. At some point I started doing content full time and realized I was making content about the process of being a content creator, whereas I want to just be doing things, like traveling or building a community, and sharing what I’m learning from that. The documentation is a byproduct. The main thing is living a life worth documenting.

Developer community and moving to San Francisco

Hannah: You recently moved to SF for a developer community role. For people who don’t know, what is that?

Yuqi: Developer community is a subset of developer relations. Dev rel is anything you do for a company that faces and supports developers of your product. A lot of people are probably more familiar with developer advocates, who write the guides and technical tutorials and give talks.

Developer community is putting together rooms where developers can talk to each other and the company, and creating a way for people to get into and use the product through their relationship with each other. I do a lot of meetups, hackathons, and moderating our Discord.

I work at an AI infrastructure company, so everyone who uses it is basically a developer.

Hannah: How did everything you were doing during your gap year lead you to this role?

Yuqi: The through line for me has been bringing people together and forming relationships. At the beginning of my gap year, I was thinking, I really want to invest in my friendships, my relationship with my family.

Towards the end, I was like, I really need a community to help me because I’m 18 months in and I feel a little lost. I need people who are similar to me. If we’re all independent builders, we can support each other and I can learn from them.

So I started hosting meetups for creators and solo founders. That community was really helpful because there were people who’d gone through the exact same thing. Plus, I just love solo founders. Every solo founder I’ve met has been a really amazing person.

I was also making tech maps of different cities, mapping interesting tech companies and startups in DC, London, and SF. Those did really well on LinkedIn. It made me feel more connected to the tech community in the cities I was in and gave me a better understanding of which companies were interesting.

If you’re job hunting, I say to everybody, make a tech map.

Walking away from product management

Hannah: PM is often touted as the ultimate tech role for a lot of people. What was it like to walk away from that?

Yuqi: I did wonder, is this the right decision? But I knew during my interviews. I did not want to continue cold-applying to product jobs. The interview process is very case study heavy now. That’s a big reason I never went down the consulting or pure finance path either. I didn’t enjoy the case study interview. I only got into product before they did case studies.

The interviews I enjoy are the ones where I just vibe better with the person I’m talking to. That’s all I can say about it.

The “9-to-5 door” and what’s next

Hannah: You once said on YouTube that going back to a 9-to-5, that door feels closed. Now you have a full-time job at a startup. How do you think about that?

Yuqi: I didn’t join a 9-to-5. I joined a 9-9-6. I’m putting in so many more hours just because I think about what I need to do for this job outside of the job. I enjoy putting on events and bringing people together. I go to a lot of tech events for fun anyway. I probably would have been showing up to community events even if I wasn’t in community myself.

And it really did feel closed at the time. If I was applying to any jobs when I made that video, I would have felt a personal block. You know when you logically know you need to do something, and you try to go through with it, and you just feel dread? I did not want to go through with those calls.

Hannah: I’ve been someone at different points who’s said a 9-to-5 is not for me. And I stand by that. I think the nuance is that neither of us has a true 9-to-5 where we clock in and clock out and don’t think about it again. It’s a flywheel with the rest of our lives.

Yuqi’s advice for people feeling stuck

Hannah: For someone feeling stuck, burnt out, not sure what to do next, what would you tell them?

Yuqi: Everybody is at their own pace. I took seven-plus years before I took this break. A lot of people feel this pressure, like I need to have it figured out sooner.

For me, it took 18 months to figure out what I wanted to do next. In fact, I didn’t really figure it out. I just felt ready to start applying to jobs, which I didn’t feel before. Then through the process of elimination, applying to many jobs and having many different interviews, I landed on developer community.

What helped me was being around people who I admired and aspired to be like, who showed me all these different paths I could take and who made it seem like, okay, I can have a salaried job, but still have a lot of freedom and be expressive and be myself.

Connect with Yuqi on YouTube, LinkedIn and Instagram!

Reads, Ideas, Tools

• WTF is a portfolio career?

• Don’t let the machines do the living

• [Podcast] Stop rambling: the 3-2-1 speaking trick that makes you sound like a CEO

Jobs & Resources

• ❓Take my career exit quiz

• cool jobs for ambitious nonlinears (updated ~weekly)

• my resources

Find me on: Instagram, Linkedin, Tiktok, Youtube

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people making big pivots.

💼 This week’s jobs in tech/startups (as always, reply to this email if you have a role you’d like to share with the community!)

Matt Shumer, an AI founder, posted an essay on X this week called “Something Big Is Happening” that now has more than 80 million views. I posted a video about it and a lot of you saw it, but short-form video doesn’t leave much room for nuance, and this topic needs it. So I want to dive deeper here.

Despite being a big vibe coder and AI dabbler in my own life, I don’t write about AI in this newsletter. It’s not my expertise and I already spend way too much time thinking about it in my 9-5. But I’m making an exception because I think a lot of you are in industries like finance and professional services where nobody is having this conversation. Frankly, even at most tech companies and startups, people aren’t having it either.

After reading the article, the counterpoints, and sitting with it for a few days, the takeaway I keep coming back to is this one:

Everyone is going to have a nonlinear career soon, not by choice, but because the linear path is going away.

“The honest version sounds like I’ve lost my mind”

Shumer said he wrote this article for his parents, not for tech Twitter. He said he keeps getting asked “what’s the deal with AI” and keeps giving the polite version, because “the honest version sounds like I’ve lost my mind.”

The honest version: he says he is “no longer needed for the actual technical work of my job.” He describes what he wants built in plain English, walks away for four hours, and comes back to the finished thing with nothing to correct.

He’s writing to people who tried ChatGPT a year ago and thought it wasn’t impressive. He says the free version is over a year behind what paying users have access to. And what he’s talking about isn’t the chatbot you ask simple questions. He’s talking about AI agents that control your browser, open multiple apps, and do your work for you.

He lays out this timeline:

“In 2022, AI couldn’t do basic arithmetic reliably. It would confidently tell you that 7 × 8 = 54.

By 2023, it could pass the bar exam.

By 2024, it could write working software and explain graduate-level science.

By late 2025, some of the best engineers in the world said they had handed over most of their coding work to AI.

On February 5th, 2026, new models arrived that made everything before them feel like a different era.”

He says this is happening in tech first but lists out every industry it’s coming for: law, finance, consulting, customer service, writing. Anything you do on a computer, and not in ten years — in one to five. He cites Dario Amodei, the CEO of Anthropic, predicting 50% of entry-level white-collar jobs gone within that window. And he says people in the industry think Amodei is being conservative.

The pushback

This shouldn’t be a one-sided conversation, and there were some responses this week that I think are worth reading.

John Coogan wrote a piece on TBPN called “AI Is Not Covid”, rejecting Shumer’s comparison of the AI revolution to Covid, and I think his core point is fair. Covid could infect anyone at any time, which is why it made sense to warn everyone. AI disruption won’t work like that. It won’t hit everyone at the same time or in the same way. A surgeon’s patients still want her holding the knife. A teacher isn’t getting replaced by a robot next school year.

Where I agree: the urgency is different depending on how close your work is to a screen. If you’re a junior analyst building models in Excel all day, your timeline is very different than a surgeon’s. If you’re in an operations role that’s mostly email and spreadsheets, you should be paying more attention than someone whose job requires them to physically be in a room with people.

Where I’d push back: I think Coogan underestimates how many people’s jobs are closer to a screen than they think. And the fact that disruption isn’t evenly distributed doesn’t mean you should wait to see if it hits you. By the time it’s obvious, the window to prepare has closed.

Then there’s Will Manidis, who wrote a piece called “Tool Shaped Objects” that I think is the most interesting counterpoint. His argument is that a lot of AI right now functions as what he calls a “tool-shaped object” — something that looks like a tool, feels like a tool, produces the sensation of work, but doesn’t actually produce work. He compares it to FarmVille: you click, the number goes up, you feel productive, but nothing was built. He says people are setting up elaborate AI workflows whose primary output is the existence of the workflow itself. The setup is the product.

I’ve seen that. But I think it actually strengthens the case for paying attention. If some people are going to waste time playing AI FarmVille while other people are using these tools to do real work in a fraction of the time, that gap is going to widen.

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Five things I’d start doing

Despite the pushback, Shumer gives concrete advice in the article and I agree with most of it. Here’s what I’d tell you, combining his suggestions with my own.

Start using AI for real. If you’re on the free version of ChatGPT, you’re falling behind. It’s like how only your mom and grandma use Facebook now. Get Claude, download Claude Code, and learn how to use Claude Skills, which is how you give AI specific instructions to do real work for you. Use the latest model, not the default. Don’t ask it questions you can google — feed it a contract, a spreadsheet, an actual doc from your job. Go vibe code something with Lovable.

As Shumer writes: “if [something] even kind of works today, you can be almost certain that in six months it’ll do it near perfectly.” Spend one hour a day doing this — not as a search engine, but in your actual workflows. He says if you do this for six months, “you will understand what’s coming better than 99% of the people around you.”

Invest in relationships. The most valuable people in 2-3 years will be the ones who can connect pieces across teams and stakeholders, not the ones who can build the best spreadsheet. Trust built over years, connecting dots across people, reading a room — AI can’t do any of that. Roles like sales, chief of staff, customer success, parts of product management and marketing are still going to matter, even if they have different titles.

Get your finances in order. As Shumer puts it: “if you believe, even partially, that the next few years could bring real disruption to your industry, then basic financial resilience matters more than it did a year ago.” Build up savings, be careful about new debt that assumes your current income is a given, and give yourself options.

Start building something for yourself. I’m not saying quit your job tomorrow. But you have a window right now where you still have income and stability, and a year from now that might look different. Start a side project, build a small audience, create something.

Build a personal brand. If entry-level roles in finance, consulting, and law are disappearing, then “analyst at X firm” stops being an identity. Your job title is not going to carry you. Being known for something will.

Every career will be nonlinear

A lot of you follow me because you have nonlinear careers, or you want one. You’re in finance but thinking about tech. You’re in consulting but want to build something. You’ve changed jobs multiple times and people keep asking what you actually do.

This AI wave is going to make that the norm, regardless of how big you think the impact will be. The stable, linear career path most people spend their whole lives optimizing for is in the line of fire. Everyone will have a nonlinear career, even if they didn’t choose one, because the linear path stops existing.

But if you've been reading this newsletter for a while, you already know how to

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operate in that world. The five things above are the same things that have always separated people who navigate change well from people who get caught off guard: use the tools, invest in people, stay financially flexible, build something of your own, and make sure you're known for more than your job title.

And above all of them is the one skill that always compounds: learning how to learn fast. The people who will be fine aren't the ones with the best current job or the most stable industry, but the ones who can pick up new tools, adapt to a new normal, and figure things out in real time.

Reads, Ideas, Tools

• “Something big is happening” by Matt Shumer

• “AI Is Not Covid” by John Coogan

• “Tool Shaped Objects” by Will M.

Jobs & Resources

• cool jobs for ambitious nonlinears (updated ~weekly)

• my resources

Find me on: Instagram, Linkedin, Tiktok, Youtube

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for ambitious people with unconventional paths. Follow me for ~weekly posts on pivots, portfolio careers, and personal brands.

💼 This week’s jobs in tech/startups (as always, reply to this email if you have a role you’d like to share with the community!)

I sound like a broken record every time I say this, but my favorite part of building a personal brand over the past year has been meeting people through content. I’m constantly grateful for the smart, thoughtful community that’s found me and resonated with what I share.

That’s why I’m excited to share this conversation with Andrew, who started his career in investment banking, moved into private equity, and transitioned into an operating role at a startup in London. He originally found me through content and has shared his story with me over the past year. (Small world - Andrew is also a Columbia grad who moved abroad to work in banking!)

In this conversation, we talked about how Andrew made sense of each move, what banking and PE taught him, why he started questioning the distance between his work and its impact, and what it actually looked like to try to pivot out of finance.

We also get into the less glamorous parts of the process: applying to dozens of roles, doing case studies while working full time, being seen as “too finance-y,” and learning to trust intuition over perfect analysis.

If you’re thinking carefully about your environment, motivation, and what kind of work you want to be closer to in the long run, I think you’ll find this one useful.

Early career and optionality

Hannah: How would you describe your career so far?

Andrew: I usually think about it in terms of values, because those have driven every move.

In college, I didn’t have a clear idea of what I wanted to do. I studied comparative literature and political science at Columbia, and I was interested in a lot of things, but nothing stood out as an obvious career path.

That background trained me to think critically, synthesize ideas, and connect things that are not obviously related. But when it came time to choose a job, I was worried about boxing myself in too early.

Finance felt like a place where I could build transferable skills and keep my options open. I also wanted something technical. I considered consulting, but learning how to understand businesses through financial statements and numbers felt valuable.

Banking and private equity

Hannah: What was banking like for you?

Andrew: The culture was very execution-driven. You are rewarded for saying yes, putting your head down, and doing things the established way. There is not much incentive to think creatively.

What stood out to me was how removed the work felt from actual decision-making. Even senior people were mostly pushing paper around. At the same time, I was constantly interacting with investors and felt like they were the ones actually shaping outcomes. That’s what pushed me toward private equity.

Hannah: Did private equity feel different?

Andrew: In some ways, but the core issue stayed the same.

I ended up in a niche credit investing role at Carlyle, focused on NAV lending. The work was intellectually demanding, but I still felt very far removed from the underlying businesses. We spent a lot of time writing long memos, building detailed models, and adjusting assumptions, and I kept asking myself what the real impact was.

Culturally, I also struggled with being in financial services more broadly. There is a lot of anxiety driven by fear of losing money. People tolerate difficult environments because of that fear, and over time it becomes draining.

That combination made me start questioning whether this was the right long-term environment for me.

Deciding to explore something different

Hannah: When did you start seriously exploring roles outside of finance?

Andrew: Earlier in 2025. I started pretty casually in the spring, just taking conversations and looking around, and then I really ramped things up in May and June.

Hannah: What did that process actually look like?

Andrew: Much harder than I expected. I applied to 99 jobs before signing an offer.

I completed around ten case studies, usually spending six to eight hours on each. That was honestly the most draining part of the process.

A lot of companies were very risk-averse, especially when it came to candidates switching industries. Even when I felt qualified, I could tell there was hesitation.

Hannah: Hesitation in what sense?

Andrew: Even my current company mostly hires former MBB consultants. Coming from finance, I was very aware that I wasn’t the obvious candidate. There was definitely a perception gap around whether my background would translate.

Hannah: How did you think about risk while making the switch?

Andrew: Financially, startups are obviously riskier. I tried to mitigate that by being selective about where I spent time.

I focused on companies founded by people with deep industry experience who had identified a clear gap in the market. I also cared that my current company isn’t VC-backed. It’s funded by revenue and angel investors, which made the business model feel more sustainable to me.

At the same time, staying where I was felt risky in a different way. I knew I needed to leave, even if the next step wasn’t perfectly defined.

Finding the role and positioning himself

Hannah: How did you actually find your current role?

Andrew: I took a very methodical approach on LinkedIn.

I searched for people in London with Ivy League backgrounds working in tech, not finance or consulting. A lot of people still fell into the latter categories, which made filtering easier.

When I found a company that looked interesting, I reached out to someone who was a Columbia alum. That initial conversation led to interviews.

The entire process took about four months and included multiple rounds and case studies.

Hannah: What did you learn about yourself during that process?

Andrew: Initially, I targeted strategic finance roles because they felt like the safest fit. But through the case studies, I realized I do not enjoy owning models or spending all day in Excel.

That pushed me toward broader roles like business operations or chief of staff.

The way I positioned myself was by emphasizing learning speed. I studied literature and political science, then learned finance from scratch. That story helped people feel more comfortable with the transition.

Life at a startup, careers and intuition

Hannah: How have the first few weeks been?

Andrew: The culture has been the biggest difference.

There is a strong emphasis on transparency and openness. My managers are approachable and involved, which I really value after my previous experiences.

The workload is real, but I am not working weekends, and I feel comfortable pushing back if needed.

The company is at a growth inflection point. A lot of my work is focused on revenue operations, defining our ideal customer profile, and building outbound strategy. That will be a big focus going forward.

Hannah: Looking back, what stands out about how you’ve made career decisions?

Andrew: Overthinking has never solved my problems.

Every meaningful transition I’ve made was driven by intuition. Either I was being pushed away from something that no longer felt right or pulled toward something that felt more aligned.

Trying to perfectly analyze the next step kept me stuck longer than necessary. Taking action and adjusting afterward has been far more effective.

Hannah: Looking back now, is there anything you miss about private equity or finance more broadly?

Andrew: I respect the attitude in finance of “we will get this done no matter what it takes.” My senior colleagues pushed me to my limits under this mantra, but also unlocked a sense of belief in myself despite adverse circumstances. My recent career switch is a good example of how natural it felt to push myself through rounds of interviews and case studies — I had lived experience of perseverance paying off despite some short-term pain.

Hannah: For someone in private equity or finance who’s considering a move into startup ops, what do you think they should be clear on before making that leap?

Andrew: Be honest with your intentions. Why do you want to leave your current job, and why might you thrive better in a new job? Many people in banking and PE have never had to truly question their occupational purpose, since for many IB → PE is a safe, default “path” out of college. The sooner you’re honest with yourself, the sooner you’ll find a path that truly fits you.

Also, use your company diligence skills to your advantage. As a startup employee, you’re effectively an equity investor in the business, so don’t be afraid to bring a DD list to management and grill them a bit. Good CEOs will appreciate your critical thinking, and solid answers reflect a good place to park your capital.

Trust that you’ve done enough thinking. Take action, then reflect. The answers will come quicker this way.

Connect with Andrew on LinkedIn!

Reads, Ideas, Tools

• Shopify President: While Everyone Chases AI, Sell These Products

• Inside the invitation only stock market for the wealthy

• WisprFlow: Voice dictation that helps me write/respond 10x faster

Jobs & Resources

• cool jobs for ambitious nonlinears (updated ~weekly)

• my resources

• a mini AI tool I made to help you write cold emails

Find me on: Instagram, Linkedin, Tiktok, Youtube

💼 This week’s jobs in tech/startups (as always, reply to this email if you have a role you’d like to share with the community!)

There’s a term I came across last year that finally put words to something I’ve been thinking about for years.

The Bermuda Triangle of Talent.

Simon van Teutem, an Oxford grad who turned down offers from McKinsey and Morgan Stanley, coined it after studying why the smartest people at elite schools keep funneling into banking, consulting, and law.

His research explains how these firms cracked the psychological code of insecure overachievers, drawing them in with money, status, and optionality. By the time they realize they’re deeply unfulfilled, they have “golden handcuffs” on and can’t leave.

As a former investment banker who fell into the prestige trap, I admire Simon for bringing this to light with research.

His proposed solution involves better institutional design—places like Y-Combinator or Teach for America that redirect ambitious people toward more meaningful work.

But as someone who quit banking, applied to YC and considered impact-oriented work…and still felt stuck for a long time before exploring several startup roles and the creator economy, I think institutional design is only part of the story.

YC has become its own prestige trap - many high-achieving young people building the millionth “AI-powered B2B SaaS meeting note app” for the money and status, not because they want to solve real problems. And a lot of TFA people I know ended up in banking afterwards. Institutions never change as fast as we need them to.

What’s actually shaking things isn’t a new institution. It’s that the old ones are falling apart.

McKinsey is thinking of cutting 10% of staff. Goldman and Morgan Stanley have conducted multiple rounds of layoffs since 2023. Big Law lays off more associates every year. Tech laid off 100,000+ people in 2025 alone.

The golden handcuffs are coming off whether people want them to or not.

I’ve seen this in my own path and in others around me. We’re pivoting, starting businesses, buying small companies, joining the creator economy, building side hustles until they can go full-time…

Not because any institution told us to, but because we’re figuring out what actually matters on our own terms.

This is my story of getting sucked into the Bermuda Triangle of Talent, quitting, hitting rock bottom, and eventually finding my way out through startups and the creator economy.

This is what I wish someone had told me when I was deep in it.

How I got sucked in

In college, I was never a finance major. I landed an internship in Sales & Trading at Morgan Stanley knowing close to nothing about banks and converted it into a post-grad offer. After a few months working full-time, I realized S&T wasn’t right for me. I was more interested in digging into one company’s operating model than tracking how 100 stocks traded on a short-term basis.

So I read enough Wall Street Oasis articles to convince myself that Investment Banking would be the best place to learn. I also convinced myself I would gladly trade a consistent 60-hour week in S&T for 90-hour weeks in IBD because the work would be more interesting.

Classic Bermuda Triangle logic: optimize for exit opportunities, prestige, and “learning” without asking whether I’d actually like the work.

I hustled. Applied to every opening. Studied accounting ratios like crazy. Got rejected again and again for lack of experience. Eventually made it into a sector coverage team through an internal transfer.

The gratification of finally landing my long-coveted IBD job lasted about two months. The thrill of getting staffed on my first deal. The fast-paced environment where I was learning new things about the sector every day from smart people. The new title on LinkedIn. Building my first model. Not thinking twice about being at the office on a Saturday. Wearing 90-hour weeks as a badge of pride.

I knew it was coming—but when the non-stop Friday night staffings, page-long 3am comments, and 100th version of an already perfect slide deck came, they came and they didn’t stop.

I stopped learning. I stopped performing at a high level. Instead, I was constantly fearful of the work to come. I quickly realized that 90% of the work I did on any given deck or model ended up being unnecessary, usually because of poor communication and planning from management or clients.

I became miserable, anxious, and unhealthy. Every waking moment spent with my friends and family became an endless complaint about the injustices I suffered and the pointless comments I stayed up all night to turn. I dreaded weekends. I was constantly anxious to receive messages and phone calls on nights out. The negativity poisoned and paralyzed my attitude and my relationships.

I needed to quit.

Rock bottom, then somewhere new

I felt lighter the day I quit. The day after, I felt like a complete failure.

What had I just done? I threw away everything I’d been working towards for years. I’d never make that much money again. What would I say to my classmates making associate at PE firms while I was unemployed?

If so many people went through this for longer and handled it well, why was I so weak? Wasn’t this exactly what I had signed up for?

I tried to escape by changing my environment. I left to backpack in South America with my boyfriend at the time. Of course, you can’t escape yourself. My relationship fell apart, and I found myself jobless, single, and directionless in a hostel in Patagonia wondering if I’d made the biggest mistake of my life.

I spent months at what felt like rock bottom, eventually moving back in with my parents. I read books like Design Your Life, The Pivot Year, and The Mountain is You. All great books, but they didn’t give me the clarity I craved.

Eventually I started applying to jobs. I didn’t care about the title or industry. I just wanted to work somewhere that had nothing to do with finance and sounded interesting.

I interviewed with a tech company hiring for a Product & Operations role launching a food delivery platform in Mexico City. I didn’t care about Product or Operations or food delivery. But Mexico City sounded fun.

A few months in, I was shocked to find that I actually liked my job. I went from working on $50M deals I didn’t care about to $10 food deliveries that I felt obsessively responsible for. I talked to our customers and drivers every week. When things broke, I saw it within seconds. When things worked, I saw that too.

I was still working a lot sometimes, but it didn’t feel the same. There weren’t pointless last-minute fire drills. No 100 versions of a PowerPoint deck that was already perfect. We were trying to do things quickly and well enough to get them into market.

We helped thousands of drivers and small restaurant owners make a living. The business grew fast. I got promoted after a year and led a strategy team for new launches across Latin America. (Not bad for thinking I’d be bad at every job after banking!)

After five years abroad between Hong Kong and Mexico City, I went back to the US for business school. I got an MBA, interned as a Big Tech PM (found it wasn’t for me), and eventually landed in product marketing at a startup. I started building content on the side and turned it into a six-figure business that I’m excited to keep building every day.

It’s been a nonlinear path. I took a pay cut to work at my first startup, but I’ve since tripled my income doing work I actually love.

The escape isn’t linear

Leaving the Bermuda Triangle isn’t a single decision. It’s an ongoing process, and here are a few things I’ve learned:

Don’t do it for the prestige (…but it’s hard not to). Prestige was why I did banking, got an MBA, and tried Big Tech PM. When I stopped optimizing for prestige—taking the Mexico City job, joining a no-name startup, building content—things got better. That said, I can’t say I’ve fully escaped. Maybe I’ve just replaced banking prestige with follower counts, honors like LinkedIn Top Voice, or “top VC-backed startups” on my resume. The pull is always there, but now I’m more aware and know how to fight it.

It’s okay to quit. It's okay to not buy into the suffering culture that leads to burnout—the idea that you need to undergo 2 years of grueling hours to "earn" a good exit opportunity…of doing more of the same work that drains you. The institutions won't change as fast as we need them to, but we can. People don't talk about why they quit these prestigious institutions or what went wrong because they want to preserve a certain image. I'm telling you mine. Share yours. Find people who will tell you theirs.

You can’t think your way to clarity or courage. I read all the career books. I journaled. I optimized my fitness routine and diet on paper. None of it gave me real answers. What worked was trying things—taking the Mexico City job on a whim, building content on the side, writing the first page, doing the first workout, surrounding myself with the right people, saying yes to opportunities that sounded like an insane detour.

The Bermuda Triangle experience is a double-edged sword. It isn't all bad. Banking made me much better at quickly analyzing information, structuring communication, and getting up to speed on any company or sector. And let's be honest—the prestige still opens doors, even on unconventional paths. In content creation, saying you did banking gets attention. There's a reason every article about Simon’s research mentions McKinsey and Oxford. But swimming in the Triangle also made me prestige-obsessed, less empathetic, more rigid, and deeply impatient. This takes years to undo.

People are everything. In banking, I rarely felt like my teammates were in the trenches with me or cared about my development. At my startup jobs, I built relationships with people across the world I still lean on today. When you’re on a path to doing something different, you need to be around others who share your journey. Startups and content helped me do that. If you’re only spending time with people from your past life stuck in the Triangle, you’ll feel bad about yourself and get dragged back into comparison traps.

The Triangle gives you clues if you pay attention. It can be overwhelming to figure out what you actually want all at once. What helped me was noticing the small binaries. I liked talking to companies about their business model, but hated formatting slides at 3am. I liked building an operating model from scratch, but hated the 100th round of comments on it. Eventually those small observations became a larger conclusion: I like analysis, but only with a clear link to action. This led me to become an operator in tech and a creator on the side—not an analyst. You might find the opposite to be true.

Work-life balance isn't the fix (at least for me). Between my startup job and building content, I probably work more hours now than I did in banking. But it doesn't feel the same. In banking, it was the irregularity and lack of agency that killed me—the sudden Friday notice of a deck due Sunday night, the uncertainty of whether I'd get summoned over a holiday weekend. That created a constant anxiety. Now, I wake up every day and know I've chosen how to spend that day. I have flexibility, support from teammates, and ownership over what I'm building.

If you're the type of person trying to escape the Triangle, you're probably not going to be satisfied with a chill 9-5. Maybe a chill 9-5 that gives you space to build something on the side—but not one where you're just coasting.

I’m no longer in the Triangle. Or at least, I’m swimming toward the edge.

And I've been thinking a lot lately about what would have helped me when I was deep in it. The career books didn't do it. The self-help stuff didn't do it. What actually helped was finding people who were on a similar path, trying things that didn't fit neatly into a traditional trajectory, and learning from others who had figured out pieces of this before me. Not just the career stuff, but the life stuff too: the mindset, the personal development, the whole picture.

I’m working on something for people who are ambitious, thinking about what’s next, and maybe feeling a little stuck. If that sounds like you, I’d love to learn more about where you’re at.

I’d be grateful if you’d take 5 minutes to fill out this survey. Your answers are shaping what I build next, and two people who complete it will win a $150 Amazon gift card.

>>> [TAKE THE SURVEY] <<<

Jobs & Resources

• cool jobs for ambitious nonlinears (updated ~weekly)

• my resources

• a mini AI tool I made to help you write cold emails

Find me on: Instagram, Linkedin, Tiktok, Youtube

💼 This week’s jobs in tech/startups (as always, reply to this email if you have a role you’d like to share with the community!)

📣 I’m building something new, and I need your help 📣

I’m working on something new for people who are ambitious, thinking about what’s next, and maybe feeling a little stuck.

If that sounds like you, I’d love to learn more about where you’re at right now.

I’d be grateful if you take 5min to fill out this survey. Your answers are shaping what I build next, and two people who complete it will win a $150 Amazon gift card as a thank you for your time!

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One thing I’ve come to appreciate more as I get older is learning from people who are a few chapters ahead of me, especially when their paths look different from what I imagine for myself.

These conversations tend to challenge my assumptions in the best way, because if there’s one message I want you to take away from my content, it’s that there’s no one right way to build am ambitious, successful career.

Ed Essey is a Senior Director at Microsoft who built a 20-year career at the company and grew an Instagram audience of 100K+ in just the last few months, creating content for high performers in corporate.

There’s something grounding about hearing from someone who has seen multiple cycles, made tradeoffs over time, and built conviction slowly instead of chasing every new opportunity.

We talked about how Ed built cross-functional influence early in his career, why he started advocating for better work instead of waiting to leave, and the moment he realized his internal credibility wouldn’t translate outside Microsoft. We also discuss how he grew his Instagram to 100K+ followers and the framework he uses to help high performers who feel stuck.

(here’s a candid too!)

Starting a Career During the Dot-Com Crash and 9/11

Hannah: To start, how would you describe your early career?

Ed: I graduated from college in 2001, which was an absolutely wild time. The dot-com bubble had just burst. A week before finals, my job offer was rescinded. I already had an apartment in Mountain View and had moved out there early.

Then a second offer was rescinded. A third one, I showed up for one day, got called into jury duty for three days, and when I came back, the office was gone. Literally butcher paper on the windows. The company had shut down without telling anyone.

Hannah: That’s a pretty chaotic way to start a career.

Ed: It really was. At one point I was doing the classic “five MIT guys in a basement” thing while interviewing. I flew out to interview at Microsoft, and that same day our startup was supposed to put out a press release to attract VC funding. That day was September 11th.

I flew into Boston. Family was panicking. VCs stopped answering calls. Everything froze.

Around the same time, my girlfriend’s father wanted me to work for him at Enron. Enron had just collapsed too.

So I ended up taking a job at Microsoft, even though I didn’t see myself as a Microsoft person at all. I saw myself as a startup guy.

Why Ed Stayed at Microsoft

Hannah: And yet you stayed.

Ed: Yeah. What’s funny is Microsoft kept putting me on “startup” teams internally.

I worked on early versions of products like InfoPath and Office Server. Later I moved into DevDiv working on parallel computing. Almost everything I worked on was net new.

Every year, I was still interviewing externally. I always thought I’d leave.

Hannah: What kept changing your mind?

Ed: Every time I’d get an offer elsewhere, I’d go to my manager and say, “I want to work on different problems.” And my manager would say, “I agree. Let’s shape your role around that.”

Over time, I realized something important. I didn’t actually need outside leverage to advocate for better work. I just needed to articulate what I wanted to learn and why it mattered to the business.

So my role kept changing. It kept getting better.

Hannah: That kind of support from a manager feels pretty rare. How did you build that kind of relationship?

Ed: I was explicit about what I wanted to learn and how it tied back to real business outcomes. I didn’t frame it as dissatisfaction. I framed it as growth.

Managers respond when you’re thoughtful about impact and not just personal advancement. Over time, that builds trust.

Hannah: When you say you advocated for better work, what did that actually look like?

Ed: It meant having ongoing conversations about scope and direction, not waiting until I was burned out. I’d say, “Here’s what I’m seeing, here’s what I think I could contribute, and here’s why it matters right now.”

It wasn’t about asking for permission to leave but rather proposing a better use of my time.

Leaning into to Public Speaking and Teaching

Hannah: Was there a moment where things really shifted for you?

Ed: Yes. At one point I said, “I want to get really good at design thinking.”

I talked to the central design thinking group, and they said, “Actually, we think you’re already one of the best people at this. Would you teach it?”

Hannah: You’ve said you were terrified of public speaking. What made you say yes anyway?

Ed: I knew it was the thing I needed to do, even though it scared me. I didn’t feel ready, but I felt called to it. So I said yes.

I spent a year teaching design thinking to engineers, eight hours a day, about 200 days and I trained over 22,000 engineers. That experience completely rewired my confidence.

Hannah: Did you realize at the time how much that year would change things?

Ed: Not at all. I thought I was just developing a skill. Looking back, it changed how I saw myself and what I believed I could do.

How Cross-Team Collaboration Became Ed’s Source of Leverage

Hannah: You talk a lot about cross-group collaboration. Was that something you intentionally built towards in your career?

Ed: It was intentional very early.

People act like working across teams is reserved for senior leaders. But I joined one team late in its lifecycle and immediately saw how much integration opportunity there was with other groups.

Because I was new, building a relationship with someone on another team took the same effort as building one on my own team. So I just started doing it everywhere.

Over time, I built a huge network of trust across the organization.

Hannah: Did that change how leadership saw your role?

Ed: There was a moment that really stuck with me. Microsoft used to rent out the Mariners stadium for internal all-hands.

Bill Gates got on stage and talked about how important it was for one product, InfoPath, to connect with the rest of business. And I realized he was describing my job. That’s when it clicked that what I was doing was strategically meaningful.

How to Build Influence Beyond Hierarchy

Hannah: You coach a lot of people now. What do you see holding them back?

Ed: People get very hung up on hierarchy.

There’s a psychological behavior called leveling. People are constantly assessing whether they’re above, below, or equal to someone else, and then behaving accordingly. I never did that. I treated everyone as a person trying to solve a problem.

Hannah: You mentioned that you have a metaphor you use for this.

Ed: Yeah, the puppy analogy.

If a stranger rang your doorbell and handed you a puppy, you’d be confused. Even if you like dogs, it’s weird. A puppy isn’t free. It changes your life.

That’s how a lot of people try to add value at work. They show up with solutions before understanding context.

Hannah: What does that look like in practice?

Ed: It means understanding the other person’s circle first. Their goals, constraints, incentives.

Once they see you as part of their circle, trust forms naturally. Otherwise, you’re just handing people puppies they didn’t ask for.

Why Ed Built His Personal Brand

Hannah: You already had strong internal credibility. What made you realize that wasn’t enough?

Ed: About ten years ago, I started thinking, what happens if I get laid off?

My business card opened doors, but not because of me. Because of Microsoft.

If I lost the title, my name wouldn’t carry me anywhere.

So I started building a brand around my thinking. Writing, blogging, posting on LinkedIn, speaking, and eventually getting invited into innovation communities around the world.

Ironically, that helped Microsoft too, because I could bring outside experts into internal conversations.

Later, I got cancer at 37. That was the real forcing function.

It made me deeply aware of how short life is. I realized my calling was helping people understand their worth and use their gifts to make meaningful change.

Creating Content and Learning the “Language of Instagram”

Hannah: You eventually moved to Instagram. How did that happen?

Ed: I wasn’t even an Instagram user. I had maybe 220 followers, mostly friends and family.

At first, I talked about innovation and intrapreneurship, which was my area of expertise. It didn’t work.

I had to learn the “native language” of the platform.

I found that what resonated was the term high performer, especially people navigating politics, burnout, or toxic environments.

Once I reframed my message, things clicked. In six months, the account grew to over 100,000 followers.

The content that resonated most was about toxic bosses, not because people wanted to complain, but because they wanted more agency.

The Framework For High Performers Who Feel Stuck

Hannah: You create content for high performers. Who do you consider a high performer and how do you help them?

Ed: First, I don’t define “high performer” for people. If you believe you are one, you are.

What I see consistently is that high performers struggle with boundaries because they don’t know what they’re protecting.

So I teach a framework I call the Four Cs that every high performer should get clarity on:

• Core — who or what you won’t let down

• Calling — the impact you want to make

• Care — how you care for your body, mind, and environment

• Community — who nourishes you and whom you nourish

If you don’t know these, boundaries erode. Decisions become reactive. Burnout follows.

Everything else — navigating toxic bosses, career growth, leadership — builds on that foundation.

What’s next for Ed

Hannah: As you look ahead, what’s exciting you most right now?

Ed: I’m really focused on my book, The Inside Job, which comes out February 12.

It’s about everything we’ve talked about here. How people build leverage, influence, and meaning from inside the systems they’re already in, without waiting for permission or blowing everything up.

Writing it forced me to put language to patterns I’ve seen over decades. It feels like a natural next chapter.

Connect with Ed:

• Instagram

• LinkedIn

Ed’s book, The Inside Job, will be available for purchase on Feb 12. Learn more about it and sign up at https://edessey.com/book for early and behind the scenes access.

I hope this conversation was helpful if you’re wondering whether reinvention always requires leaving your environment, or if you’re starting to build your personal brand.

If you have a story you think should be shared, my inbox is always open!

Reads, Ideas, Tools

• How to spot a breakout startup

• Jack and Jill: I tried this tool that lets you get on a call with Jack, the AI recruiter, who helps you get hired at top startups. Most “AI recruiter” tools feel scammy or generic, but this one somehow understood the nuances of Product Marketing in B2B vs B2C, so I’m bullish - give it a try if you’re looking for clarity (and leads) for your next step

• A new approach to living a good life comes from a most unlikely place

• Podcast: if you have multiple interests, do not waste the next 2-3 years

Jobs & Resources

• cool jobs for ambitious nonlinears (updated ~weekly)

• my resources

• a mini AI tool I made to help you write cold emails

Find me on: Instagram, Linkedin, Tiktok, Youtube

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for ambitious people with unconventional paths.

Subscribe now

Follow me for ~weekly posts on pivots, portfolio careers, and personal brands.

5 questions to ask before you start a newsletter

Out of all my content channels, this newsletter has been the least strategic yet most rewarding.

I got back from the holidays earlier this month and opened Instagram to see three different people announcing new newsletters. Then I checked LinkedIn and saw two more. Everyone is starting a newsletter in 2026.

It makes perfect sense. People are tired of short-form content. Consumers are tired of quick dopamine hits that keep them in an endless scroll. Creators are tired of fighting algorithms - they look to long-form for higher quality engagement with audiences they own.

The newsletter makes for an attractive side project or creative outlet. The startup cost is one of the lowest. You don’t need to film or edit, and writing on Substack feels less cringey than broadcasting to your network via reels or LinkedIn posts.

I started this newsletter a little over a year ago. I have over 9,000 subscribers now. And yes, I recognize the irony of writing a newsletter about writing a newsletter, but I wanted to share my experience for anyone starting or thinking about starting one.

I’m not going to tell you about my great, well-researched newsletter growth master plan. I never had one. I started a newsletter a few months into creating content on Instagram because I panicked about the algorithm controlling who saw my content, changed my approach multiple times, and spent months feeling overwhelmed by the idea of writing it before having everything figured out.

If you’re thinking about starting a newsletter - whether you’re exploring an idea or side project outside of work or adding a channel for your personal brand - here’s what I wish someone had told me before I started.

1. Why start a newsletter?

The owned audience argument (and the tradeoff)

If you’re still reading, you’ve decided that a newsletter might be a good way to broadcast your thoughts to the internet. You’re weighing it against other channels - short-form video, LinkedIn, whatever else you’re already doing or thinking about doing.

A newsletter lets people get to know you, how you think, whether they trust you. Eventually they might buy from you or stick around long enough that you can monetize the attention through partnerships, land speaking opportunities, or even get a new job out of it.

The big selling point is that a newsletter is an owned audience - no algorithm controlling who sees your work. But here’s the tradeoff: growth is much slower than social media because there’s no algorithm to push out your work. You’re asking people for their email instead of a follow. That’s a higher bar. (Yes, Substack has some built-in discovery - more on this below!)

As a marketer, the convention I’ve heard is to have one long-form and one short-form content channel you’re good at so you can balance the pros/cons of each.

The best deciding factor

Do you like to write?

I love to write. Looking back, it probably would have made more sense for me to start here instead of with Instagram. If you don’t love to write, a newsletter can feel like drudgery. If you prefer creating in another format more, start there instead. That said, writing a newsletter can also be a great way to improve your writing.

Two models for thinking about ROI

As an ex-finance girly, no I can’t forget about the ROI! There are two ways to look at a newsletter - a binary but useful heuristic.

1. Your newsletter can be your product - paid Substacks where the newsletter itself is what people pay for.

2. Your newsletter can be marketing for your product. Your product might be you - your personal brand, just your ideas if you start it for fun. Or it might be how you sell courses, coaching, other services.

For me, it’s the second one. I use my newsletter to build a specific audience and occasionally sell sponsorships.

I don’t substantially monetize my newsletter itself and that’s intentional. I have 2 paid posts that I only gate because we value what we pay for more. I’d only do this with high-value guides. (Maybe I should with this one, but it feels weird to gate a newsletter post about starting a newsletter!)

I use it as a deeper form of engagement with my audience because I don’t have time for consistent creation on YouTube. And I’ve found it’s a valuable additional channel for sponsorships.

2. How do I start?

Platform: what I tried and what stuck

I’ve tried three platforms. Compare more platforms.

Beacons (don’t) I started here because that’s what I used to collect emails in my Instagram link in bio. Beacons isn’t built for email. The editing experience is poor, you need a lot of formatting and templating. Skip this.

Kit (depends on your use case) I moved here after hearing the founder speak at an event. I’d heard good things and it was cheaper than Beehiiv at the time. But the pricing scaled as you grew in ways that made more sense for brands selling programs or digital courses because they need drip campaigns, growth loops, all that infrastructure. Wrong use case.

Substack (where I landed) The editor is simple. I like that there’s discovery built into the platform. I’ve heard creators who prioritize their paid newsletter offering say it’s not the best because of platform fees, but I like it here for now.

Figure out who you’re writing for

Same advice goes for starting any personal brand: know your why, your audience, and your positioning. Your newsletter is just an avenue for your brand. It’s less about picking a niche - more about an angle or specific audience you write for. I wrote one of my few paid posts about this.

Getting your first subscribers

This is personal. You need to test.

More than half of my subscribers came from Instagram because I was collecting emails through lead magnets before I even started the newsletter. Substack has some discovery built in - you can grow through Notes. I also grow via Linkedin by restructuring every newsletter as LinkedIn posts and link back to Substack for the full read. Your first subscribers could be friends and family. Your most sustainable growth may be through shares and referrals.

Good exercise: Think about whether someone in your target audience would share each post as you write it.

Newsletter growth guide from Beehiiv

3. How do I sustain it?

The time commitment (and the invisible work)

1-2 hours per week, give or take, but probably more because I’m thinking about it all the time. Every week I know what I’m going to write about before I sit down. I think about what questions my audience might ask and start answering them in my head before I open the doc.

Making it sustainable

You have to enjoy it or make it enjoyable. If you’re challenging yourself to do this, create a ritual. Saturday morning. Coffee and breakfast. Deep thinking time.

This is my weekly anchor to think about my audience - who they are, how they think, how I connect with them, what I want to say.

How I never run out of content

Create content flywheels. You might remember my welcome email where I ask what you’re interested in and what goals you have. I get topics right there. (If anything, my problem is too many ideas.)

Use LLMs (strategically). I created a Claude writing style of my voice. I dictate drafts using voice, get Claude to structure it, and review/rewrite the whole thing. I’m fastidious about how I sound on long-form and I’ll take a few typos over AI slop. If you ever see me use the word “quietly” when it makes no sense in the context, I’ve been hacked.

I repurpose like crazy. Whenever I go on a podcast, speak at an event, or have a conversation with someone interesting - boom, that’s a newsletter.

4. How do I grow it?

Where my subscribers come from

Here’s my growth over the last 90 days. Imports are from lead magnets, Instagram is through my bio and stories.

The cold start problem (and how I avoided it)

I didn’t have a cold start. I used free lead magnets I distributed on short-form to get a few thousand newsletters. You can also start on Substack and grow via Notes.

You need to give yourself an initial boost, but the best long-term growth hack is writing good content. Think of your newsletter as your product and short-form as your marketing.

How this became my content flywheel

My newsletter content has been chaotic and inconsistent until recently.

I wrote a few posts last March and April. I had no idea who I was writing for or what consistency meant. I tried to match my lead magnet topics. That was fine but I struggled to find ideas that I cared about. It also felt like one more thing to create.

Then I switched to a weekly jobs list that my assistant helped curate. I still include this in every post. It drove growth but not engagement or trust. A jobs list is a utility - people aren’t learning anything about you.

In November, I decided it had to change. Brandon Smithwick writes about content and mentioned his version of a content flywheel in his newsletter - a long-form piece that feeds everything else.

That’s what my newsletter became. It’s the central thing I do every week. Even if I don’t do anything else, I write this. It gets repurposed into at least one Instagram carousel, one video, a few LinkedIn posts. It’s also a thought exercise. I get deeper on my thinking around one topic and research it thoroughly.

My subscriber growth after I stopped being lazy with my newsletter in November:

5. Is it working?

How to measure success

Go back to which operating model you’re using (newsletter as marketing or newsletter as product).

Set three metrics: one acquisition (subscriber growth), one engagement (replies or shares), one outcome (related to your goal - could be booked meetings, link clicks, or sponsors).

My newsletter is working (I think)

I have an email list ready for when I launch something. The trust, engagement and ownership often feel more meaningful than my 100K audience elsewhere, even if it doesn’t bring in as many direct dollars yet.

It gives me clarity of thought and an anchor for consistent messaging across channels every week. It helps me stay focused on building for an audience, not an algorithm, and it makes me a better writer in my 5-9 and my 9-5!

Reads, Ideas, Tools

• 10 new interesting startup and side-project ideas: good products for your newsletter to market!

• a16z: How to hire a Chief of Staff

• Breaking into strategy: good post on people who want to work in strategy, especially if as fractional advisors/consultants.

Jobs & Resources

• cool jobs for ambitious nonlinears (updated ~weekly)

• my resources

• a mini AI tool I made to help you write cold emails

Find me on: Instagram, Linkedin, Tiktok, Youtube