Eventually, I did. Not always, not all the time, but some of the time for some of the things -- maybe even much of the time! -- and that was good enough. Most of the time. :)
And maybe it's a little scary that despite having been a filk guest of honor at a number of filkcons (and God bless the folks who asked me), and being a member of the Filk Hall of Fame, and a filk dealer and filk producer, I occasionally get a bit rankled because I feel like I am just not cool enough. Now part of this is because I'm a thoroughly lousy self-promoter, I suspect, but -- on the other hand -- maybe I'm just as happy not doing that kind of self-promotion. The good things that happen to me tend to happen not because I asked for them to happen, but because people genuinely wanted me involved. And that feels pretty darn good.
There are things that I'm not much good at musically. I never really learned how to sing harmony, having been told by the folks in junior high school choir that I couldn't sing. I took this to heart and didn't sing, except that I'd wander around my high school chemistry lab singing quietly to myself and then I wouldn't believe anyone who told me "You have a nice singing voice" because I'd had too many people in my life up to that point who set me up to look like a fool.
I got over that. :) And I'm learning to sing harmony. Slowly and painfully, but I'm learning how to do it. Heck, it's just like singing the melody, except that it's not. (Actually, it's more like inventing a melody that adds to the main melody rather than detracting, at least as far as I've been able to work out.)
I'm not particularly useful in a band or Instaband situation though. I can play acceptable rhythm guitar or fingerstyle, but I still can't reliably sing backup, nor play a lead guitar line, nor bass (although I can cheat a bit with Frankenbass), and keep me away from the drums. :) And I am so happy that I've been blessed with friends like min0taur, Sally, markiv1111, Dorotha, catalana, Andy, and quadrivium who will work with me on album projects so that I actually have a virtual band behind me instead of just me and my guitar. And that is a majorly cool thing.
And I recognize that I probably could learn how to do some of these other things, but, you know, there's just a finite amount of time in life and there are other things that I've decided to do instead. So that'll just need to be ok.
In the meantime, I have a good job which I (usually) enjoy. And I have a good group of friends.
And in my copious spare time, I work on conventions, I produce albums, I have an improv comedy troupe, I'm half of a small-press book publisher, and I write songs. And I can make you laugh (usually in combination with daisy_knotwise), and I can make you cry, and sometimes I can just make you go "aw".
And in a month or so, I'll have someone new to start teaching the songs to.
And that's all pretty cool.