A friend of mine is a wonderful musician who never “made it”, but continues to play bars and restaurants and small venues weekly, as he has for 30+ years. He’s done some session work as well.

Another friend said he feels bad for him because he never lucked into greater fame, but he’s too good to give it up.

As long as he’s happy performing, I don’t see this as a bad thing. I can go see him perform regularly, he seems happy, he has a dedicated local following.