Interesting that you brought up the pain of failure. I find I can handle the pain better when there's some success mixed in with the failure. But - this is weird - when I think about my life, I mostly remember the embarrassing moments, the times I've hurt and disappointed people. The times I've been wrong. I know I done good things too. Why can't I remember them.?
I think failure is hardest to handle for those who had a lot of success early on. I was smart, got good grades, behaved. Then, after college, suddenly no one was interested. And I see a lot of young people going through the same thing - they hit that point - usually somewhere around twenty - when suddenly life is smacking them down instead of supporting them. I think of all the child stars that end up on drugs and in all kinds of trouble. Some do okay, but a lot of them don't.