I've come to accept that I "start over" because I like to keep learning. I love- no I need - to fight new problems and learn new domains. From physics to teaching to sailing to jiu-jitsu to (web) programming to business (which I thought, arrogantly, was going to be rather simple) it's what my brain craves.

It's a curse in some ways. It seems to me that my ego is under far more attack than it should be at my age, as I am never the deep-knowledge expert about any topic. And I don't bluff very well.

On the other hand, I can't seem to have it any other way. It's probably a form of arrogance: "Of course I can do that, hand me that [chalk | gi | keyboard | main sheet | ...]

I imagine we are a lot alike.