I've struggled with this a couple of times. In each situation it came down to a single question (or series of questions, actually). 1) Will I be more fulfilled

I've struggled with this a couple of times. In each situation it came down to a single question (or series of questions, actually). 1) Will I be more fulfilled if I try it, even if I fail? 2) Will I learn from it and grow as a person? If I can answer yes to both of those questions, then I do it. I ask myself these questions to almost everything I do. And yes, sometimes that means not doing what I _want_ to do, if I don't have the time, energy, or the means to do it. For example, I really want to go to Sweden this year, but I have to save for a few other things that are more important to me and my life (business, learning scuba diving, etc).