Playing the Game in the Real World

In school, i find it so strangely punitive that you should only be allowed one chance to try to demonstrate your skill or ability. It's so different om the real world, where we're always telling people, if at first you don't succeed, try and try again. Part of it is that we haven't designed society as well as we've designed some games. Could we make simple changes like that that better tap into our natural ability to enjoy challenge?