One could argue that being over confident and facing the consequences is probably more preferable to being under-confident and never taking the risks. I probably lean more that way and there is something to be said for having the cajones to just go all in on something without over analyzing and second guessing yourself. Sure when it doesn't work out the hindsight kicks you in the butt, but for the most part it's a lot easier to ask forgiveness than ask permission. From yourself I mean.