On career discovery

0. How this came about

Before I recognized coaching/therapy is what I wanna do professionally, I still was somehow drawn to that kinda activity and did a decent amount of pro bono career coaching for a few years while still working as a quant. It was an outgrowth of my active presence on r/quant (apparently very few legit quants have the personality to be active in giving advice/opinion on such forums.. which in retrospect makes perfect sense) and folks reaching out to me, as well as of a desire to “give back” and “save others from my mistakes” as a lot of the people I talked to were either considering PhD or, most commonly, on the crossroads about what to do next towards the end of their PhD. Between that and various friends graduating or changing jobs or whatever and looking for advice, as well as writing advice, I spent hundreds of hours on this.

Then came my own career discovery journey during which I thought about and discussed the issue with various people at length. I also read a few of the top books on the topic: “Designing your life” (DYL) is the absolute best and a must-read for everybody.

1. Basic approach

This is gonna be skewed towards gifted as that’s the demographic I’m most familiar with: implication of being gifted for career discovery is higher importance of fit and higher willingness to abandon okay things in favor of searching for great things - as the value of a gifted individual really finding themselves and blossoming is huge.

This is also gonna be biased towards high intentionality and away from serendipity and making the best out of cool opportunities that pop up, as that’s the life I lived. There’s certainly a strong case to be made for making the best use of available opportunities, and even for making career moves aimed at increasing optionality more so than anything tangible. Idiosyncratic opportunities oft would be both a great fit (given they don’t pop up randomly but come to the prepared) and higher value than lining up to some crowded line to enter some standard path.

There’s research showing humans are terrible at predicting how a new experience (or a job) would make them feel. See this Dr K video on how intellect’s trying to pretend that instead it does know can create problems: intellect always comes up with some plausible answers when answered “how would being a programmer feel like”, and then one might feel they actually do know what it would feel like given all those plausible sounding answers. But they really don’t, especially for something as complex as working a job. This is important to internalize.

What the above means, as emphasized in DYL, is that one needs to adopt a design approach, with testing and prototyping as cornerstones of the process. Before one runs the experiments though, one needs to have their measurement tools in a working condition. That means self-knowledge, self-awareness, having mental health issues as resolved as feasible.

Alexithymia, limited access to one’s emotions, is particularly problematic (and common, estimated 5-10% general population, higher in males, I bet higher in techies and terminally online) as it often results in a lost or limited access to one’s real emotionally valent wants and hopes and dreams, and even forgetting how those feel like and substituting purely rational ideas for those dreams without even realizing what one is doing.

Beyond mental health, a very common source of career choice mistakes is being driven by somebody else’s expectations: parental, societal. These are tricky as they have some real feelings behind them (“Dad is proud of your starting your residency”, “Ppl think the startup I’m working for is so cool”), even more so if regularly reinforced. Combine that with many careers self-reinforcing lock-in dynamics - external validation from raises, promotions, but also joy of mastery and growth and new challenges - and one can ride some not quite satisfactory train all the way to the mid-life crisis (though Dr K mentions those epiphanies now happen earlier, with less societal pressure to stick to unsatisfying jobs).

How to avoid this pitfall? Awareness goes a long way: knowing that this is what my parents implicitly promoted, and that is what society implicitly promotes (be it via money or status or some unique prestige like with academia or arts), and trying to see how big a role that plays in your motivation. Having a period of freedom and play and exploration (this can be early college pre-commitment, or working some chill job which one doesn’t want to stay in for good, or a literal break), coming from a place of safety and okayness and curiosity about whatever passion one discovers rather than only certain answers viewed as acceptable, could also help. Self-discovery trips like hiking the pacific crest trail alone are also great for allowing one to be with themselves for a long uninterrupted time and do all the processing that waits to be done.

Related to watching out for external expectations is having awareness of shoulds vs wants. That’s usually a part of one’s emotional awareness curriculum. This issue is oft more binding for career matters than anything else, as we tend to have more intense judgments about what is proper and acceptable to do for vocation, as well as, in the States, have the job be a bigger part of our identity, than almost anything else. “Do I want money or do I think I should want money?”, “Do I want billionaire-level success or think I should be striving for that kinda success?”, “Do I want to make an impact or think I should make an impact but actually would rather do something I find enjoyable?”..

2. Techy careers

Tech workers are hot, which is great for those for whom it’s a good fit, and potentially dangerous for those for whom it’s not. Dangerous as external factors militating towards this career are oft very appealing short-term but not that important for career-satisfaction long-term. External factors being: convenience (no credentialism, very low barriers to entry, huge liquid market in most cities as well as fully remote), perks (money, prestige via either fancy company names or “changing the world” at a startup halo). There certainly are societal pressures to go into tech (“innovation!”, “change the world!”), and in certain subcommunities they reach a fever pitch (“you gotta work an ai as that’s the only important thing in the world”). Many of those things are ofc objectively good, the point is simply that the preponderance of those external factors makes the risk of picking that career for wrong reasons that much higher.

There are a few types of people for whom I’ve seen tech be the right career choice. One is “tru builders”, folks that hacked games or wrote their own when they were 12, would spend a weekend setting up a network relay server on a raspberry pi for fun, that kind stuff. Note I focused on “unnecessary”/passion/hobby signs there - it can be hard for the untrained to distinguish signs of passion from what a conscientious/ambitious person should’ing themselves into such a career would do. I was that (I was a quant, but also looking at/prepping for tech roles, it’s broadly similar for the purposes of this post), and in retrospect it’s clear I never did any of that techie stuff just for fun and my own pleasure, but at the time it wasn’t so obvious as I was reading books and papers to advance my career or solving leetcodes just fine - as there seemed to be enough of an external reason (get good, advance career, fancier job) to do so.

Another is folks for whom real passions can’t be made into practical careers, or for whom a single unmonetizable passion is important enough that they’d go for the dissatisfaction of having a day job that is not a vocation. This is a tricky subject and a complicated design space to explore as ofc with many passions one can find a career that is closely enough aligned if imperfect. Canonical example here is music, given how impossible a career there is and how hard the experience of performing might be to replicate with more plausible jobs.

I haven’t worked with those ppl closely enough to know yet, but it’s plausible for some people external motivations are satisfying enough - though it’s rare for the communities I’ve been around, as ultimately “nerds” are those who chose/were compelled to choose their own unconventional truth over social success and fitting in. I can imagine for more conventional people some mix of winning and status and validation and social success and ambition might be enough to make this a sustainable choice, provided they reasonably like techy stuff.