Aim to Fail

This sounds really smart, but I don't know if it is. Let's say you want to be a great basketball player. If you're short and fat, you won't be one, no matter how much you practice. Michael Jordan was an incredible natural athlete. It's true that he's more than that: there are lots of incredible natural athletes who end up working at gas stations, and maybe some of them would have made the NBA if they had been as willing to fail as MJ. But if you're not naturally athletic (or extremely tall), you will never be a great basketball player. Period.

The second problem is that the fear of failure is, in the right context, fantastic motivation. You will never do anything well if you don't care about it, and if you genuinely care about something, you will come to hate failing at it. I've never met a good chess player who took losses well.

My suspicion is that it's important to do a lot of practice where failure is cheap and a lot of practice where failure hurts. But I'm not a very successful person, so I have no idea.