A year and a half ago my best SoWal friend tried to hook me up with a job that would have been rully rully cool, but I let my insecurity get the best of me and ran. Within two months I regretted it.
The good news is that after feeling like a complete wuss, I've taken a lot more challenging (to the point of scary!) jobs since then. The first one was last summer, teaching at a fine arts camp. Completely over my head, but the director of the camp thought I could do it and I figured that was good enough for me. (That same guy liked me so much that he later got me a job playing for a local theatre group. I was the musical director of my first big-deal show in the spring, which opened the door for other shows.)
I liked the camp job so much that I decided to get my master's in music ed. A month or so ago, I was approached about yet another job that was way over my head, teaching both drama and band at a private school here in town. I really wanted to work at this school, but didn't so much want to fail at it. So I called my best SoWal friend, who told me that I could do it and that I should do it.
I was unofficially offered the job today. (At church--I will supposedly get the official call tomorrow.) I'm still skeered of all the things that I don't know about this job, but I'm excited, too, because I know I can figure it out.
Thanks, Best SoWal Friend. As soon as my summers are open, I'm coming after that original job I shied away from...
p.s. This also means that come January, I don't have to dig any more holes for a while!
Congrats! How exciting to be offered such a position. 
