Winning the Pulitzer is not that big a deal. I have seen hundreds of plays that have won the prize and you couldn't sit half way through it. The Pulitzer is a common prize that means very little.
I wasn't born an artist. I was really good in science as a kid. I probably shouldn't have been an artist because I'm much more interested in science. But I was raised by artists. I can't really escape it.
I say if you're going to take a chance on something, you just go full balls to the wall.