How Much Is Enough?

Whenever the debate to end something comes up, whether it be a career or a relationship, there's always the question of what if. Some people are very skilled at just letting things go, but, there's people like me who just can't NOT explore all the outcomes. Why is that? Why do we hold on to things so desperately even though we may know they aren't healthy? I think everyone would rather have it not work out and be heartbroken than having the 'what if' constantly hanging over their heads. This is such a struggle for most people. It's so sad that everyone is so prone to misery and will constantly seek it out, even if they don't know they're doing it! I guess that's the sad truth of life though. It's easier sometimes to be comfortably miserable than to risk trying for happiness.