Choosing a career path when you’re uncertain

At 22, on my first day at my first real job, I became convinced that I had doomed myself to a mediocre career.

Instead of applying for a prestigious consulting job like my UVa peers, I had become paralyzed by inaction. My career decision felt both intractable and impossibly high-stakes: either my next job would put me on the fast-track to success, impact, and meaning; or I would condemn myself to a self-perpetuating string of mediocre gigs. I was like Esther from The Bell Jar, starving at the foot of the fig tree, and my indecision was rewarded with a single wretched job offer from my friend’s sympathetic father, writing loan servicing valuations for $37K/year.

That one year with RP Financial is as close as I’ve ever come to an emo phase. Finally, like a volcano of angst, I completely upended my life, and discovered and expanded my self-efficacy in the process. I was unlocked by two great ideas about navigating the ambiguity of pivotal career choices, especially when you’re uncertain. One idea, from Why Greatness Can’t Be Planned, applies to the lucky few that have an abiding curiosity they might pursue, but who aren’t sure where it leads. The other idea, from So Good They Can’t Ignore You, showed me what to do when I didn’t have any such curiosity.

I know that there’s a lot of content written about this topic, but I think that my perspective is somewhat unique as I’ve pivoted my career twice, each time to my great satisfaction, over the course of four separate sabbaticals.

Strategy #1: follow your curiosity, if you can

The main idea of Why Greatness Cannot be Planned is that it’s not effective to set goals when you’re venturing forth into unknown intellectual terrain. Instead, you should engage in novelty search. In practice, this means trusting that pursuing your curiosity for 12-18 months will lead you somewhere innovative. It’s well worth the read; here’s a summary from ChatGPT:

"Why Greatness Cannot Be Planned: The Myth of the Objective" is a book by Kenneth O. Stanley and Joel Lehman that challenges the conventional belief in setting specific objectives as the path to achieving greatness. Instead, the authors argue that greatness often arises from exploration, serendipity, and the pursuit of novelty. They introduce the concept of "novelty search," an algorithmic approach that values open-ended creativity and the discovery of new possibilities over predefined goals. The book emphasizes the limitations of rigid objectives, advocates for embracing the unknown, and provides examples from various fields to illustrate how transformative breakthroughs often occur through unexpected paths and serendipitous discoveries.

Unfortunately, at 22 I didn’t really feel any particular curiosity. My curiosity was awakened in proportion to my sense of agency and in response to my increasing exposure to meaningful experiences over the course of my 20s. Around the age of 30, after several years living in a group house, I had became powerfully curious about community living environments that were compatible with families, to the point where I spent a majority of my free time building projects for coliving houses, studying and thinking about them, and engaging with local communities. Eventually, it started to interfere with my ability to allocate creative energy to my day job. In June 2021, encouraged by this idea, I quit my fulfilling career as a machine learning engineer to pursue community full-time… whatever that meant, and wherever it led.

It sounds fun, but the day-to-day experience is actually rather uncomfortable and frustrating. You hit frequent dead ends, constantly wonder whether you’re wasting your time, and feel like an unwashed degenerate whenever a respectably employed friends asks what you’ve been up to (it’s crucial to have friends that understand what you’re doing, and these friends mainly hang out in San Francisco).

I often felt that I was wasting my time. It was only when I zoomed out and asked myself whether I felt like my ideas were improving from month to month that I could tell that I was making progress.

I quit with a vague plan to pursue independent research into community. 21 months later, I’m building a multigenerational campus that vastly exceeds my initial hopes and goals and have a coherent and tractable strategy and am financially sustainable.

If you want the more detailed story, you can check out my semi-regular project updates. Notice the gaps around November 2021 and August 2022 — those were long periods of doubts so severe that I nearly gave up. The life of complete structurelessness is an emotional rollercoaster. It’s not for everyone and requires a strong support network, ideally including people that have done similar things before. I met with a group of friends every two weeks for months, and it got me through my first and most major doubt phase.

There are a couple of common beliefs that I updated in the course of this process, that I sometimes see holding people back from fully grokking the mindset.

One is the idea that I needed a credible path to impact before I could get started. In reality, ideas unfold over months and years, and it’s totally OK for them to seem dumb or pointless in the beginning. Don’t worry about it and have faith that your curiosity will eventually lead you to interesting places. The patron saint of this mindset is Richard Feynman, whose Nobel originally came out of a fascination with spinning plates. In practice I found that the scope of my ambition naturally and gradually expanded as I accumulated little wins.

The other is the idea that you need to have a business plan. Keeping in mind that all advice is context-dependent and that I’m not particularly motivated by money, but: I always trusted that if I created real value for people, that down the road I would find a way to monetize. Keeping in mind that all advice is context dependent and fully disclaiming any disasters that ensue from following this advice that may be idiosyncratic to my situation: this strategy totally worked for me. I mean, sure, I may have run through all my savings and perhaps maxed out a credit card. But I also won a cool grant and am now on the path to indefinite financial sustainability doing work that feels incredibly meaningful and exciting, and that will probably result in more long-term wealth than my other career paths anyway.

My takeaway from this possibly idiosyncratic experience is that following the gradient of aliveness unlocks vast stores of energy and creativity that you simply can’t sustainably access from a place of self-coercion.

Strategy #2: if you can’t, maximize usefulness

None of that advice was useful to me at 22, because I, like most schmucks, had no obvious passions.

In fact, I found advice like the above to be actively unhelpful. It made my angst worse. I felt only jealousy at the lucky few that had discovered their passion early in life.

This is why I’m so thankful for So Good They Can’t Ignore You, which persuaded me that passion can follow mastery. Take it away, ChatGPT:

"So Good They Can't Ignore You: Why Skills Trump Passion in the Quest for Work You Love" is a book by Cal Newport that challenges the conventional advice to "follow your passion" when choosing a career. Instead, Newport argues that building valuable skills, or "career capital," is the key to finding fulfilling work. He suggests that passion often emerges as a result of becoming highly skilled and gaining autonomy, mastery, and impact in one's work. The book emphasizes the importance of adopting a "craftsman mindset," which focuses on continuous improvement and delivering high-quality work, and encourages readers to seek opportunities that align with their values and allow them to make meaningful contributions.

Thanks to this idea, I decided to quit my job in finance and become a programmer, reasoning that the high skill ceiling would advantage somebody with enough desperate energy to systematically study for many years, like me.

I would quit my job in finance, spend the $10K I had saved up on living expenses for 3-9 months of full-time studying, and read textbooks in mom’s basement until I got a job. I went to Meetups and asked entrepreneurs to give feedback on my strategy and even secured a backup job offer from Edward Jones. I finally pitched my slightly concerned but ultimately supportive family by PowerPoint — basement secured.

Looking back, I’m pleased to report that So Good They Can’t Ignore You completely aligns with my lived experience pursuing mastery. I got my first taste of competence within a few months and felt a glimmer of passion for programming. This kicked off an extremely blessed virtuous cycle of self-improvement, which I came to deeply associate with improving my life circumstances, which only stoked my hunger for more learning. My value as an engineer allowed me to pursue candidate passions that gradually emerged between 2015 and 2020, including education, preparing the job marketplace for automation from AI, and finally AI research directly.

If you’re interested in all the curriculums I Hoovered up, here’s a breakdown. If you wanted to speedrun that path, though, I’d recommend you go to the Bloom Institute of Technology, get a job, get settled at that job for 6-12 months, and then work your way through the Bradfield computer science curriculum. Within a few years you’ll have plenty of useful skills.

Trust the process

One of my consistent beefs with the Internet is that so many of us participate in self-mythmaking. We’re all conspiring to make ourselves seem more impressive. The overall effect is to disempower readers, who conclude that they’re just not made of the same stuff. I promise you: it’s all bullshit and nearly everyone you pedestalize as brilliant is just a normal person. I’ve lived with a lot of outwardly impressive people, and honestly a lot of my self-belief simply comes from observing them struggle just as much as the rest of us normal people. Each of my two pivots came only after a year of angsting about it, like a kid standing at the edge of a high dive.

Pursuing an original or impactful career requires a ton of energy and creativity. You can coerce that energy out of yourself for as long as 10 years, but eventually you’ll burn out. The only sustainable path is to follow the gradient of aliveness, if it’s accessible. If it’s not, make yourself unambiguously useful. In both cases you have to trust that the process will bring you somewhere interesting, even if you can’t see it clearly in advance.