It’s been around eight months that I’ve finished my previous job as a software engineer and have been working on my own thing(s). As you can imagine, this was a decision I took time to think through. I’ll share some elements of the thought process here, on the off chance it’s useful to someone else. I’ll focus more on the questions than my answers, because I’m a bit of a prude.
The overarching question to munch through is "what1 do I want2 to do3 in life4?". Each term is important and the phrasing is deliberate (see the superscripts; rest assured the rest of the post should read better than Greek philosophy).
1 what — we’re trying to figure out the subject and contents of our days and years in this galaxy
2 I want — inward-looking; we could have phrased the question "what should I do in life?" We’re basing our question, and subsequent reasoning, on the selfish premise that internal calling supersedes external pressures
3 to do — action-oriented and not results-oriented; we’re not asking "what do I want to be in life?" These are closely intertwined and there is no clear one-way causal relationship. If a kid tells you “I want to become a football player” there’s probably a mix of “I want to play a lot of football” and “I like the sound of being a well-known football player”. I find it more helpful to focus on the action rather than the result though, as it’s more discriminatory. It’s easier to like the sound of being Mbappé than to genuinely want to spend the majority of your waking hours playing football. To take Rockefeller’s words “I do not like money, what I like is making money”
4 in life — in the largest sense possible, although in my case I’ll be focusing on work-related things (to me, work and life are not separable)
Granted, it’s a bit of a daunting question. You might not have a single answer, and the answers probably change over time. And that’s ok. Embracing the complexity doesn’t mean we can’t make progress towards finding our set of answers at time point , to be updated every so often.
To start working through the question, I found it useful to warm up on some (slightly) easier ones as intermediate “results”.
“What do I want” -> A useful prequel is to figure out what’s important to you. What are some personal values that you hold?
“to do” -> What do you enjoy doing for its own sake? Is there an intersection with what’s important to you?
“In life” -> What would you like to be able to look back on and think, fuckin’ell, I had a pretty good run. What would failure look like (invert, always invert)? Do these images of success/failure answer to what you enjoy doing and what’s important to you?
As an example, here are some things that are important to me, in no particular order: - Independence & Freedom (intellectual, financial, personal agency) - Learning & Understanding - Contribution - Health. This intersects nicely with high level activities I enjoy the most: competing (sports, games, in whatever really), understanding and building new things (reading, thinking, writing, coding). Notice these aren’t super granular, I’m not saying “I enjoy tennis” (which I do), but I’m trying to extract what I enjoy about tennis, and that’s mostly the fact that it’s 1v1 competition with all the satisfaction that comes with it.
We’re slowly starting to converge towards something workable for life-related decision-making. To take my case, there are some obvious bad choices that would lead to ‘failure’ in a personal sense. Going to work for a large entity (company, government) for an extended amount of time is probably a bad decision if I’m seeking out intellectual and financial freedom while maximizing learning rate. I don’t think I could look back on 40 years of working at a large corporate and qualify that as a good run. The options I see as plausible: academia and/or startups. They may seem foreign to each other at first, but there are similarities. No badging in and out, no dress code and leash in the form of a tie, more intellectual freedom, more room for personal agency (less so for academia than entrepreneurship), incentive structures that maximize learning rate, plenty of competition and opportunities for real greater-than-self contribution. There are also obvious differences, the main one being the currency. Academia mainly trades on influence and reach in the form of citations and recognition, entrepreneurship on dollars. Ideally, I’d like to mix elements of both, but I’ll start with the dollars. I won’t go deeper into the reasoning of my personal choice here, but there are also exogenous factors, like the rapid deployment of AI across industries, that make the case for now being a fairly unique time to go and build a company.
Once (and only once) you’ve spent a lot of time thinking deeply about all of the above and writing down your own answers, you can shove it up your butt. I mean this semi-seriously, if you’re faced with an actual decision that is heavily influenced by the reasoning we’ve been working through (as I was - “should I quit my current job to try and build this other thing”), you can’t completely rationalize the answer. Complex decision making under uncertainty doesn’t give you the luxury of getting to the best answer with brain power alone, you also need to trust your gut. There’s some pretty good evidence to this, both anecdotal (e.g. many highly successful CEOs who are paid for their decision-making abilities, like the CEO of Accor, report heavy-handed use of gut feeling in decision making) and scientific (study on trading ability - granted it's a tiny sample size and some of the data analysis like Fig 2 is unconvincing).
Then, with mind & gut in agreement, you should go ahead and do it.