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.
I hit rock bottom at RP Financial: I didn’t like my job, my city, my friends, my future. After a year of angst, I became desperate enough to completely upend my life, and discovered my own agency in the process. I was unlocked by two great ideas about navigating my career while 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 yet 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 there’s a lot of content written about this topic, but hopefully my perspective is still worth contributing. I’ve now pivoted my career twice, each time to my great satisfaction, after four sabbaticals in 11 years.
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:
<aside> <img src="/icons/robot_lightgray.svg" alt="/icons/robot_lightgray.svg" width="40px" /> "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.
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Unfortunately, at 22 I didn’t really feel any particular curiosity, so this strategy wasn’t available to me until much later. My curiosity was blocked by my low agency and only awakened in response to a growing collection of meaningful life experiences.
However, around the age of 30, after several years living in a group house, I had became powerfully curious about engineered serendipity, 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, after 5 years of side projects, it started to interfere with my desire to allocate creative energy to my day job. In June 2021, encouraged by Why Greatness Cannot Be Planned, I quit my otherwise fulfilling career as a machine learning engineer to pursue community full-time… whatever that meant, and wherever it led.
It sounds fun to follow your curiosity, but the day-to-day experience is actually rather uncomfortable and frustrating. I hit frequent dead ends and felt like an unwashed degenerate whenever a respectably employed friend asked what I’d been up to. It was crucial to have supportive friends that understood my path.
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 full-time months later, after collecting “stepping stones” and gradually realizing what works and how they fit together, I’m building something that vastly exceeds my initial hopes, 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 where 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 organically 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: don’t fixate on making money too early.
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.
None of that advice was useful to me at 22, because I, like the vast majority of people , had no obvious passions at that age.