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

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There are lots of things in psychology that have stood the rest of time that are much more useful. Developmental milestones, adoption and extinction of trained habits, clinical assessments of sensory modalities at various stages of conduction.

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.

Yes, ADHD definitely seems to correlate with high openness and low conscientiousness. I've also found most self-help and productivity advice to be useless.

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.

It's never going to not be a negotiation. All you're doing is limiting your options by arguing from personality typology. What you should be doing is asking behavioral questions and digging in on the responses you get. You'll get better information about what a candidate will do and how they reason through interpersonal problems than asking them questions like "which would you prefer on your time off -- going to a party with a lot of people, or spending time inside reading a book?" Questions like that which appear on many personality inventories are so abstract as to be almost meaningless.

Also you need to understand that if you start personality testing people you will never get any truthful information from your candidates. They do this kind of testing for many retail sales roles and every sales associate you'll ever meet knows exactly how to answer every question to maximize extraversion and minimize undesirable traits. It quickly stops being a test of whether you have what it takes, unless your intent is to test whether people are deeply aware of how fake personality testing is and exactly how to game the system to get past it.

Inferring negatives from positive information sharing seems pretty adversarial to me, both in spirit and in substance.

My comment was to question why the interview should be framed as something implicity adversarial to begin with. And why it's probably better to use something like references to validate what it would be like to work with someone rather than rely on our own dubious judgement or the positively biased judgement of the candidate's.