Slow Death of an Unhappy Man

Sometimes I feel as if I'm stuck between Steps 4 and 8 of the 12-step program. By that I mean I'm making an inventory of my life while wanting to apologize to those I have wronged as I plod toward the finish line. That list includes me for all the damage I've done in the past few years. "Hey, man. Sorry for ruining your life and stuff." "It's cool. I get it: You're lost. No harm and all that."
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I'm getting over the fact that I should not have quit the best job I've ever had. I'm getting over the fact that, in 2006, I was growing into the person I've always wanted to become but let him wither into a confused and frightened child. I'm getting over (or trying to, anyway) the fact that leaving my job cost me much more than I ever expected: time, money, friendships, identity, self-worth, growth and some other, even more important stuff I have no way of quantifying. Worse yet, I've hurt others along the way.
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Right now I'm reading "Dark Nights of the Soul" by Thomas Moore. (Coincidentally I'm also reading "The Woman Lit by Fireflies" from Jim Harrison, "The Jungle" from Upton Sinclair and a find-your-way kind of self-help book from Martha Beck.) A "dark night," the way Moore sees it, is any life-altering event that thrusts one into the throes of despair and introspection but ultimately shapes him or her into a stronger and wholly different person. I'm all for this brand of change, because the guy I see in the mirror every morning isn't someone I want to know anymore.
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Turns out that Moore has some experience in this area. He has lived a very colorful life. He's a monk. He's a musician. He's a philosopher. He's a prolific writer. And he's also very human, so he has had to confront his share of life changes. He has had failed relationships. He has lost things. But he has hope for the future. Such hope begins with living through these dark nights, or painful journeys, and finding a different person standing on the other side.
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He writes in "Dark Nights" about the importance of sorting out the detritus of one's life and starting over, which is the point where I now find myself. It's terrifying yet exciting because it deals with matters of death and rebirth. He also writes about living a life based on love and desire rather than one based on rationality and control. That's where I've been: I've tried to control my life from one second to the next, too often in the wrong circumstances. At times I've been complacent and let life take me where it wishes, while at other times I've kept too firm a grip on the steering wheel. I'm not sure what this force is, this repressive little imp, but it's made me an unhappy person who's afraid to take chances. I've lost so much of myself already. I don't want to waste any more time, but Moore tells me I can't rush the process.
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There's a famous quote about the need to take control of one's own destiny lest someone else control it for him. It's a fine saying, and it applies to many situations ... but not all. So where does one draw the line? When does one exercise control by letting the brain lead, and when does one loosen the strings and let the heart do what it wants? Me, I've been a horrible judge.