I've never worked in a company
Avoiding employment was not an explicit choice I made: it's just how things ended up as I followed my passions.
(Okay, I taught piano lessons in various music schools for a couple of years, and maybe did some odd jobs here and there, but not as a career.)
While studying music in university I started working on an iPhone app for learning songs from recordings, to help myself get into Jazz music but also as a tool for other musicians and music students to improve their playing. This was a collaboration with Wil with various names that eventually became AudioScrub. Not so successful at launch, but after a year or so of more development and people starting to use it and share with friends, it became a meaningful amount—not a lot, but enough to pay my bills, stay independant, travel a little. I surprised myself by learning iPhone programming on the sixth try. It was gratifying to finally make a 'real app' after a while of feeling 'restricted to web apps', and I felt good hearing the emotion in how so many people describe that it's helpful it is to them.
And just after finishing my studies, I started a live music listings project called note the sound to help promote local music concerts by smaller, often unknown artists: I worked with local venues like restaurants, bars, and art spaces, charging a fee per event and created a technology stack that helped with data entry, showing event details, automatically publishing to social media, and generating printable calendars; for some time I even experimented with my own system (inspired by Amazon Mechanical Turk) to pay people to help with micro tasks like finding artist information.
From 2009 to 2021, my income was 40% from iOS apps and 60% from note the sound, regularly working alone. COVID-19 wiped out live music for a while, and when it came back I didn't want to continue with the same structure—customers repeatedly asked me if I would restart as they were happy with the service, which I guess was a good sign; I hope to someday try again but with a different structure where I don't need to be so involved. The iOS apps became less and less motivating because of the amount of work as a one-person operation, so I ultimately stopped. Although I didn't yet replace any of those incomes with something stable, and it might sometimes feel like a uphill battle to do so, I would say 12 years is not a bad run and I'm proud of what I've done.
I've been experimenting with a Fund button integrated into my web apps (which for me are now 'real apps'), gathering support on Open Collective, and using Ghost to power memberships for Strolling. I've often said that my goal was "to get a thousand people to pay me ten bucks a year" as a metaphor for living from passive income—in practice most people want to give me more than that, so the numbers probably will be a bit different; this might sound like a meager sum for many people, but 1) I believe that to achieve this implies that there's probably more than a thousand people and 2) I would be willing to sacrifice some comfort to maintain my freedom to spend my time on what excites me.
Obviously it can be fulfilling to be employed, have a salary, feel secure, work with a team of great people, and I respect the various reasons people pursue that path, but I'm clearly wired for something else and will try to exhaust other options before I go there.