The freedom to take unconventional career paths comes with a dangerous cognitive trap: our brain's remarkable ability to construct post-hoc narratives that justify any path we've taken. Just as PE managers might avoid marking down investments during tough times, we tell ourselves stories about how each random career move was actually building toward something meaningful.
But uncertainty itself doesn't produce upside. While unconventional paths can accelerate skill acquisition and enable opportunistic bets that institutional constraints would make impossible, one could easily wander through random risky paths and end up with subpar returns.
In this piece, I break down:
How illiquid careers actually create value
The three key processes that determine success on unconventional paths
Practical frameworks for evaluating whether you're making real progress
How to balance short-term uncertainty with long-term validation
It's true that personality tests per se might have little value in the business world. But the fact that traits cluster together in non random ways is not irrelevant to making predictions about people. Big five literature is one of the few things in psychology that have mostly stood the test of time.
Can relate to the ADHD bit and ditto on environments that are best for personal productivity. I started at a big bank, moved to a VC fund, then an early stage startup and now work as an independent consultant for a non profit now. With each move, as autonomy increased and incentives were more aligned, I found myself producing a lot more. A large part of it is that I was able to also find work that was interesting but I think the bigger factor was autonomy, alignment of incentives and whether I was judged on metrics that correspond to my strengths. It's not even like i have an inifnitely high risk appetite but for personality reasons, I've resigned myself to the fact that if i want to succeed, I have to pursue almost complete autonomy and thus expose myself to broader variance.
My hot take is that at some level, ADHD is indistinguishable from low conscientiousness - forgetting appointments, meetings, calls etc. More precisely, ADHD seems negatively correlated with the orderliness facet of conscientiousness but orthogonal to industriousness. If you're high on industriousness and low on orderliness, you sort of have no choice but to be your own boss.
Seems like you either misinterpreted or I didn't communicate as well as I should have. I'm not arguing for making interviews "adversarial" in spirit (or even in substance). I'm saying that interviews are implicitly adversarial games, inw hich the recruiter is trying to (ideally) maximize the chance of obtaining relevant signals and the interviewee isn't always aligned with that goal. Often, interviewees want jobs even if they're not a "great fit". Which is why I'm arguing for in fact a less adversarial conversation, in which you infer negatives from other positive information interviewees will excitedly share.
How illiquid careers actually create value The three key processes that determine success on unconventional paths Practical frameworks for evaluating whether you're making real progress How to balance short-term uncertainty with long-term validation
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