One of the things that struck me was how he would use a tape recorder as a kid. He would record himself playing his music so he could go back and listen to it with fresh ears. If he thought he really had something, he'd take the tape to JC Penny's, put it in a stereo, push play, walk around the store a bit and kind of sneak up on his own music as if he'd never heard it before. If he didn't like it, he'd change it, or scrap it altogether.
I guess the alternate universe story would be Ben writing some songs he was satisfied with, stopping when they were "good enough," performing for a few people who thought they were okay, never signing a record deal and complaining about the fact that his work was just never really understood or that he never had a big break.
If we really want to do great, fantastic, killer work, it's not really about having a big break or finding an audience who gets us. We've got to be as honest with our ideas as Ben is with his. And we've got to be willing work to make the okay ideas much, much better.