I quit my last "job" in 1976. I still continued making pretty good money playing music in bars. I never considered it to be work. It was a hobby for which I was paid. I earned money for traveling, meeting people, partying and a lifestyle of sex&drugs&rock&roll. Above all, it was fun.
Cheers, Jimbo! I've played about 450 (4-hour) gigs in the last 6 years, in addition to the 40-50 hours a week slave labor. I dearly love it, but I'm hauling a rebuilt 1962 Leslie cab (internally miced, line out to the PA), assorted keyboards (occasionally a real Hammond) and I live a 30 minute drive from any town.
It's still fun, but I quit for time to help with aging parents, that are 15 years older than you. I haven't played for 2 months, and that's an itch that hurts. There's some jams around, I am looking for one.
I can run with "slow 6/8, I/IV/V in G, let's go". The easy stuff.
I always found it hard to play with more than one guitarist. They tend to go off on long jammy tangents without telling me. I guess my ear wasn't good enough to pick up the chord changes quick enough.