Can you tell more about your job? I love Tokyo, but the work environment seemed to have a lot of drawbacks (general long hours, presence over productivity restricted days off) Did that change, or are you good with it, or did you find a different niche?
I'm working at Stripe, so, definitely not the traditional "wait for your boss to leave" experience. My previous was Google, and the change was as much my mental state as the work.
Really hard to know. My personal experience is that whenever I do weird shit, however, I've ended up in a better place? That is also itself a weird thing. Anyway, great comment, I just don't even know how to begin knowing the truth of this one without a personal belief based on lived experience. How would you even design an experiment to find the truth of this one?
I don't think so. If you put some effort into your fallback plan, and choose your weird shit so that it's likely to work out, I think it can just be a good bet. And it's hard to imagine working up the energy to do it if you're really happy where you are, you know?