Lifehacker published an interesting piece on How to avoid a life of regret:
According to psychologist Tom Gilovich, lead author on “The Ideal Road Not Taken,” published in the journal Emotion, our regrets that bother us the most involve failing to live up to our “ideal selves.” Basically, we’re not as bothered by the mistakes we’ve made or the things we ought to have done as we are bothered by never becoming the person we truly wanted to be. Gilovich explains:
“When we evaluate our lives, we think about whether we’re heading toward our ideal selves, becoming the person we’d like to be. Those are the regrets that are going to stick with you, because they are what you look at through the windshield of life. The ‘ought’ regrets are potholes on the road. Those were problems, but now they’re behind you.”
The author delineates the actual self, ideal self, and the ought self in what's called the self-discrepancy theory:
The actual self is what a person believes themselves to be now, based on current attributes and abilities. The ideal self is comprised of the attributes and abilities they’d like to possess one day—in essence, their goals, hopes, and aspirations. The ought self is who someone believes they should have been according to their obligations and responsibilities. In terms of regrets, the failure of the ought self is more “I could have done that better,” and the failure of the ideal self is more “I never became that person I wanted to become.”
So, chase your ideal self – not what you think you are, not what your peers want you to be, but what you aspire to be. You're going to have to make the leap if you want to avoid the worst kind of regret: not trying at all.