If you don’t know what you want, then you have reached the state of desirelessness. –Alan Watts
If you can get to this state, it’s difficult to exist for any length of time in it. Because we live in a world where desire is something that is encouraged; where we are told what we should want, and to look for areas where we lack something and to fill it up. So to have no desires can throw a person raised in this world into a funk. They feel at odds with the world and can’t move in any direction without difficulty, because they get input from every quarter saying that this is no fit state to be in, and to get out of it because it’s not good for the soul. You have no aspirations? "Well, you’ll never amount to anything with that attitude;" You feel satisfied? "Well, you just haven’t tried hard enough." We’re called upon to challenge ourselves, or find others who will challenge us. And it is good to challenge yourself if your self-worth is not tied to the outcome.
The outcome should dictate your next action, whether to try again or find some other distraction, but it should not be used as a whip for your ego. Nor should it be a reward. You just did something? It is done. Are you satisfied that it is finished? Then go do something else. Don’t dwell on it, but learn and move on.
You don’t want to relive old victories just as you shouldn’t relive old losses; they draw you backwards, and you start to look for the same thing everywhere you go. It’ll keep you from trying new things, because you’ll think a bad thing will happen, or you’ll get diverted to the same things because you remember doing well in them. But every moment is different.
And what happens to a person who is afraid to fail? Well, he will never do anything, because failure is much more likely than success. Think of how many right ways there are to do something. Now think of every other way, which, by definition, has to be wrong. What are the odds that you would hit on the right answer on your first try? Slim to none, right? But what if you fail once or twice? Now you have a better idea of the ground you are trying to cover, where the edges and pitfalls are.
The more you fail the less likely you are to fail, not just because you have eliminated a certain number of paths to failure; now you can identify the trends that led there in the first place. You learn what not to do. You can avoid failure, and achieve success as a side effect.