How to Build a Fulfilling Career and Not Get Replaced by AI
On when quitting a job feels to early, figuring out what's next, and how to build a personal brand in 2026
Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart, ambitious people choosing the nonlinear route.
“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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I love the non-linear career to entrepreneurship pipeline idea!
those who have non-linear and broad paths aka the “spiky generalists” are often the most useful and easy to work with, and have the most impact. However there’s a huge disconnect between this reality and what recruiters believe and take action on. There needs to be an educational shift for those who recruit so they can understand because they (generalizing) usually don’t!