I am in my mid 30s; reasonably successful software career, complete with failed startup.
I recently quit a job that just brought me so much stress and no joy. I like hacking on stuff but "working" has largely killed any ability to enjoy the process.
I have often thought about teaching, I've done some tech based summer programs in the past; and I think it might be a way for me to actually enjoy going to work (at least, most days). I know I'd be taking a huge paycut.
I don't have a degree; I'd love to work in an open environment; at some weird hippy school or something.
Really appreciate any tips or insights.
I'd also recommend looking at the opposite - nonprofit organizations hiring instructors for STEM courses; many of these will have the environment you described(I only suggest this because you mention that you are prepared to take a pay cut).
Lastly, I'd strengthen your profile/ resume by using online courses and certifications
I've used a variation of these tips to land teaching gigs at both private schools & nonprofits, and hope they serve you well.
Good luck!