Career Advice: Stuck in Rut?

A buddy of mine from my college days called up. We haven’t chatted in years. As we were catching up, he told me (obscuring details) that he’s living in a really nice area doing some work that he does enjoy, but he’s kind of in a rut. He wasn’t sure what to do, because that area doesn’t have a great job market, so he’d have to cut back significantly in order to get by with something else. I’ve been there. Here’s part of what I said:

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