(This is extracted from an email conversation with a friend who has gotten successful at something and then discovered he didn't actually like that thing.)
Regarding pigeonholing: I went through this kind of thing after breaking my leg, which brought me to a full stop and left me with nothing to do but stare (into space or at the TV). As unpleasant and disappointing as it is to figure out that you've become an expert/gotten well-known in something you DON'T ACTUALLY LIKE, at least you've figured out that much (I still like programming, it's just not enough to fill my life. I actually like it more now that I have the Business project). It's a huge step; sure, not as nice as simply discovering that you like something better and moving over to it, but a step. And if you don't take that first step you're just going to continue doing the thing you don't like. Like most people. Most people who hate their jobs. So it's a bummer that you got good at something you don't like, but it's a good thing you figured that out.
Next step: figure out what really inspires you. (Did you ever read "What Should I Do With My Life?" by Po Bronson? Now could be a great time). In my case, I can now look back and see that it's the very thing I've fought with and against since I was a little kid -- the idea that working sucks. And my solution, to avoid working at a company because they all suck, sort of worked and also didn't work so well because I get a lot more out of working with people.
The interesting thing is that even though I went at this project with the attitude that I was going to be one of those crazy bearded homeless guys that everyone avoids, standing on the street corner holding a sign, I keep spontaneously getting positive feedback about this project -- for example, people want me to present about it even though I don't usually mention that as a possibility (because I didn't feel it was ready). And I've been able to make some impacts here in town with some of the small businesses (something I never expected to happen). So it feels like, to use hippiespeak, "the universe is giving me positive feedback." When you figure out what your thing is, you'll probably start getting feedback like that, too.
Another litmus test I've been noticing: When I start thinking about what I'd be willing to do to support this project, it's much bigger and broader than when I think about, say, programming consulting ("well, if it makes a lot of money in a short time, OK. Or if it's Python with fun people on a fun project, OK") where I tend to narrow the possibilities. When I think about the Reinventing Business project, I seem willing to do a lot more things -- for example, I'd be willing to do a tour of workshop days (say: Presentation, followed by open spaces, followed by some kind of lightning talks) because even though travel can be hard, I know I get energized from doing things like this for that project. And a lot of that comes from feeling like I have a chance of making a much bigger contribution to the world by discovering an organizational structure where people love their jobs. It's great that I can help people learn to program, but this seems much more important and also supremely challenging. It's my own personal Everest to climb. That's what you need to find, something that seems crazy at first, but that you just can't get out of your mind until it starts to be something that you have to do anyway.
