I speculate that DFW's take on it would be something like: sure, we can reap some rewards by working hard and being prepared, but really the amount that those t

I speculate that DFW's take on it would be something like: sure, we can reap some rewards by working hard and being prepared, but really the amount that those things affect our lives is really small compared to huge, uncontrollable things, like which genetics you were dealt, or whether your parents were killed by a tornado when you were 5, or what country you are born in. We spend a lot of time rationalizing that our successes are somehow due to our efforts and our failures are somehow not our fault. We especially idolize high-status successes, like Picasso, and venerate such rationalizations when they come from such people. And we especially despise such rationalizations when they come from the poor, and so we hold silent contempt when we hear the homeless man on the subway explaining why it's not his fault he is so down on his luck. But [I think DFW might say] in the end it's still really just one fatalistic crapshoot. That's not a good reason to work harder, nor is it a good reason to slack off and just say "c'est la vie." It's not a reason for anything ... it's just how things are. I'm not saying this hypothetical DFW point of view is right. I'm just saying I don't think it has that much to do with rationalizations about past successes being used as motivation.