Bill requests a post about making career decisions: "How does one make the decision to "fish and cut bait" in their career?" He notes that some days he likes his job, and other days he feels like he's entirely not cut out for the line of work.
I have a pretty simple philosophical approach to the fish-or-cut-bait question. Fish. When faced with a "action-versus-inaction" decision I'm strongly biased toward the "action" choice. (The exceptions are for sexual temptation and for incurring substantial debt: in those two cases my bias is toward inaction.)
Here's what I would ask you about your job if we were having coffee:
1) Do you feel like what you are doing is good for the world?
2) Do you feel like what you are doing suits your temperament, that the good-for-the-world part springs more or less naturally from you being yourself?
3) Do you admire the people who are further along the path than you? Would you feel pretty good turning out like them?
4) Do you have irrational envy of any of your friends, for the way their life is ordered? Can you learn anything about what you are missing in your own life from that envy?
5) When you come home and say, "I had a great day today, I felt really good," is it because of things you did and things that happened to you that you can reasonably expect most days?
Here's what I WOULDN'T ask you:
a) What would you do if it wasn't this, and why do you have any reason to expect it would be better?
I don't think you can really see opportunities until you know what you want, at that sort of gut level that drives envy or that lets you recognize a day where what you contribute flows out of who you are. I also don't think you can really see opportunities until you let go of what you're holding on to. So if the answers to the top set of questions suggest that it's time to leave, I think that's the first decision. And then the second decision is "What now," which, luckily for me, you didn't ask.