The Late-20-Something's Professional Dilemma

On the pressure to figure out your "thing".

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A brief note: thank you to everyone who replied, commented, texted, or DM’d me last week regarding my new job and move to SF. The internet is an awesome place, and a big move is much less daunting knowing you have friends ready to help you adjust to a new geography and career.

I think, especially once you hit your late 20s, there’s a lot of pressure to “figure your career out,” and I think it’s something that a lot of folks around my age struggle with, so I wanted to share some thoughts I’d had over the last 6 months or so.

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When you’re in your 20s, 30 sounds like such a daunting age.

One reason for that, I think, is that when you’re in your 20s, people evaluate you on your potential. Going to the right school, landing the right starter job(s), having some novel life experiences, and working on a cool side project or two all enhance that potential. No one faults the ambitious-but-uncertain 24-year-old for not knowing what they want to do with their life, as long as they have potential.

That potential attracts opportunities, and in your 20s, so long as you have potential, you can experiment with different “junior-level” roles until you find the thing that clicks. Frankly, if you have the opportunity to do so, I think it’s valuable to test out a few different career arcs in your 20s. The additional exposure gives you more data points to determine what you do and don’t want to do, a lot of alpha can be created by pulling from experiences in unrelated disciplines, and, let’s face it, when you’re 50 years old, no one is going to care if you found your “thing” at 25 or 28. What matters is what you did in your “thing” once you found it.

But as you approach 30, people quit caring about your potential (or, at least, it certainly feels that way), and they want to see what you’ve done with it. “Potential” is a call option with an expiration date: if you don’t cash it in, it expires worthless. While, of course, no one expects you to reach your professional peak by age 30, you would ideally 1) have a firm idea of what you want to do with your career and 2) be well on your way to making that idea a reality. As we get older, our career optionality decreases because we age out of “junior-level” roles. Eventually, if you don’t find your “thing,” you are forced to settle into the last “thing” you did, even if it’s against your own wishes.

Maybe you think I’m exaggerating, but this is what my early career has felt like, and from talking to others around my age, I know I’m not alone.

If you’ve been reading my blog for while, you probably know I went to business school at Columbia. What you might not know is that I was accepted to CBS as a college senior through Columbia’s deferred enrollment program. Basically, I would have to work 2-5 years, then I’d go to business school, then I’d go be a banker or consultant or whatever. Locking in a future MBA from a good school at 22 was fantastic because it de-risked the next five years of my life. In May 2019, 22-year-old me knew that he had until ~May 2024 to figure out his “thing,” and he could try all sorts of things along the way.

So I tried all sorts of things.

For the last five years or so, I’ve oscillated between two personalities: the finance guy and the writer, the quantitative and the creative, and I tried my best to combine these two sides whenever possible.

My first job after college was in corporate finance, I had loose plans to go into banking after business school, and I was obsessed with the stock market. At the same time, I found myself publishing deep dives on various SPACs behind an anonymous Reddit account, I regularly covered different stocks on Seeking Alpha, and I launched two Substacks, one for personal finance and one covering my travels abroad, after quitting my job in August 2021.

From November 2021 to January 2024, I served as the editor and do-a-little-bit-of-everything business operations guy for a popular daily finance newsletter, a role that kept me close to the markets without actually working in them. In business school, I worked on various marketing/content/editorial strategy projects with a couple of venture firms, thinking that I could force my two interests, markets and writing, to come together in a unique role.

During my second year of business school, however, I had two realizations:

1. This combination of content/marketing/writing/whatever and finance likely wasn’t going to be a clean fit for a job role, and it made more sense to pick one or the other for my post-school job.

2. It was important to participate in the primary function (or, at least be as close as possible to the primary function) of my employer. This meant either investing, or supporting investing efforts, within an investing group, or truly working in “media” if I wanted to do media.

I needed to make a choice: media or markets. Media seemed to be the obvious answer: my newsletter had grown quickly, I had spent two years serving as the editor for a large newsletter where I played a significant role in our ad operations and managed a team of four, and I was trying to land a book deal. So I leapt at the opportunity to help Robinhood build a media subsidiary. It made perfect sense: I’d have a high degree of autonomy on what I wanted to write about, and I’d get to help build a new media outlet from scratch.

I was pumped.

Seven months later, I felt a pit in my stomach as I realized that I did not, in fact, want to work in media. I loved writing, but I didn’t particularly love media or journalism. When you have to write several columns a week for your job, writing in your free time ceases to be a “fun” activity for you to unpack your thoughts. It feels like an extension of your job. It also becomes painstakingly difficult to write a book after work when you’ve already spent all day writing other stuff.

There’s some cliché that says not to turn your passion into your day job because it turns something that you previously loved into “work,” and I regret to inform you that, in my experience, the cliché rang true. I wanted to make a change.

Normally, when a white-collar 27-year-old living in New York realizes that they want to make a career change, they apply to business school, weave a compelling narrative for why an admissions committee should accept their application, recruit with different companies in different industries, and reinvent themself over a two year period.

It was incredibly ironic, then, that I managed to double down on media after school, only to realize, in less than a year, that media was decidedly not what I wanted to do long-term.

So what do you do when, no longer protected by the wonderful safety net known as “business school,” you realize that the thing you thought you wanted to do isn’t actually what you wanted to do?

Well, before anything else, you panic. Then, piling on that panic, you tell yourself, “You seriously fucked up, didn’t you? You’re the one guy who decided that they want to make a sharp career change immediately *after* their business school window closed.”

The pressure you feel to find your “thing” when you’re having second thoughts about your career in your late 20s is suffocating. It’s this ever-present, Sisyphean stressor threatening to crush you, as you think to yourself that the trajectory of the rest of your life is entirely dependent on your next job move. It’s all in your head, of course, but that doesn’t make the pressure any less real.

There is a silver lining, however.

Pressure, especially self-induced pressure, to figure out your next thing is a powerful forcing mechanism. I hadn’t felt that much career pressure from 2019 to 2023, because 1) I was enjoying myself and 2) I felt like I still had time to figure it out. But over the last six months, that pressure felt existential. It felt like I was running out of time to “figure it out,” and if I didn’t “figure it out,” I would have wasted the “potential” that I’d built up in my 20s.

If you poll a group of strangers on their biggest fears, I imagine that you would hear a collection of answers like, “dying,” “public speaking,” “flying,” and “family illness.” But I think, for most people, the real answer to this question lies deep in their subconscious, and it only surfaces it when risks becoming a reality: the fear of not capitalizing on one’s potential.

Fortunately, you can, in my experience, “figure it out.” By your late 20s, even if you haven’t found your “thing,” you likely have enough life experience to 1) know, at least broadly, what you want to do, 2) know what you don’t want to do (which is arguably more important that the previous point) and 3) know how (or, at least, can figure out how) to achieve point 1).

You don’t have to (and probably won’t!) get all of the details perfect. And that’s okay! You have an entire career to do that. You just need to capitalize on one opportunity that points you in the right direction. When you’re certain that the thing you’re doing isn’t what you want to do long-term, and an opportunity emerges that aligns with your longer-term goals, you go all-in and figure out the details later.

This is, in a nutshell, what was going through my head in the fall, and it’s also why I’m about to pick up and move across the country.

From talking with friends and peers around my age, I’ve noticed that this pressure to find your “thing” when you’re second-guessing your career at this stage is a universal phenomenon. The stress is real, as you feel like the rest of your life is dependent on figuring out your next move. So if that’s you, I have two things to say:

1. You’re not crazy.

2. With a little urgency and agency, you can figure it out.

- Jack

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