I think it goes back to my high school days. In computer class the first assignment was to write a program to print the first 100 Fibonacci numbers. Instead I wrote a program that would steal passwords of students. My teacher gave me an A.
I really don't think life is about the I-could-have-beens. Life is only about the I-tried-to-do. I don't mind the failure but I can't imagine that I'd forgive myself if I didn't try.