I ended my career in June, and I am attempting to entirely reinvent my professional life at 36. It's interesting going through this sort of open ocean search having a little bit of savings and stability, but the stakes feel higher (emotionally) even though, rationally, I am in a better position to take on risk than when I was young and completely broke. The hardest part of it is actually deciding what do I want from…
I imagine that if I was doing what you are describing, I'd enjoy keeping busy while still having most of my day to pursue something new. And having my side job (that pays or not, who cares?) help push me forward into learning something I couldn't easily do on my own.