Let Go

Letting go is hard for me. Sometimes people, sometimes things, sometimes ways of thinking. I'm a person who likes to stick to a schedule. In 3 1/2 years of college, I missed one class. In my 4 years of playing LATA tennis, I've missed one day of regular play. I rarely call in sick to work. I think it stems from some irrational fear of what might happen if I don't do something, even though I know what will happen is probably nothing. It's a little control-freakish.
I'm watching "Gossip Girl" as I write, and in voice-over, Gossip Girl herself just said this:
"Sometimes the most important thing to know is when to get out, and when to give in."
I know Blair Waldorf and Chuck Bass's "Dangerous Liasons"-like war has nothing to do with where I'm at in my life, but I think my obsessive side tends to hold on and hold out too much. I don't take risks and I don't like to upset my status quo. I tend to stick around too long just because I'm afraid. Fear is rarely the best motivator.
There are things I'm thinking about letting go of, there are other things that I want to take risks on. I don't know how to figure out what I should do, but isn't the fact that I'm thinking about them so much a sign that I should be doing something about them?
Should I be like Jenny who quit her job? Should I be like Blair and go meet Chuck on the roof? Should I be like Serena and hold out on the offer? It's "Gossip Girl," so I'm sure everything will end badly. But aren't we all better off for them taking the chance?