I used to run a theatre program for homeless youth. The theatre director had this quote from Shakespeare in Love (and film stills from the scene) on his wall. It pretty much sums up not only theatre, but non-profit work, and the world of small business. It would seem my career choices reflect a lot of blind faith on my part.
I never really know if things will, in fact, turn out well. Plenty of things in my life have turned out really badly, entirely by chance. I don’t necessarily expect or assume that things will turn out either well or badly, but I guess I choose not to worry too much about it. As a recovering perfectionist, what I do know is that worry is useless. So is guilt. You can’t learn anything by worrying or feeling guilty, so why bother? Regret is different; you can learn from regret and do things differently the next time. But most of what we worry about never comes to pass anyway, while much worse things happen unexpectedly. Better to be able to cope in a real crisis than prepare for an imaginary one. And guilt is a terrible motivation for anything; acting out of guilt will almost certainly not turn out well.
In the end, it’s a mystery. Why spoil it?