>What’s even worse is when they do things like this post where there are little jokes about how it’s a financial burden to change careers or take a break rather than acknowledging how they have no risk of running out of money.

I mean, I didn't read it like this. It is absolutely a horrible financial decision to quit a top position at google to go back to school and then try to be a comic (one of the hardest jobs to get paid anything for). I didn't take "bad financial decision" as "fatal decision that will land him on the streets".

>I’m not sure what I’m supposed to take away from it other than “must be nice.”

It's just a dude with a blog who clearly has engaged readers making a big update to his life (that may indirectly affect some readers who are involved in AOSP). I didn't take it as some pity party.

But my personal take is that it's okay to not spend your life minmaxing finances. and it's okay (if it's in your power) to "restart" your career, or make a lateral move. If you want to have a more cynical take: At some point money is made to be used and he has so much money that more money is less important than a true passion. If you ever make that much, consider it ass well.