Ask HN: Any tips on getting into teaching at private schools?

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.