I DJ for a living (also a producer and do a little graphic design for extra money) and have been since I was 17......very well known in my city. Probably dj 3-4 times a week.
I've absolutely love it but for me it's become like that love you have for a trophy wife. Beautiful, wildly passionate but I'm just not getting all the benefits I could get from something less flashy.
I'm at a crossroads in life in that I have a degree but I'm simply not making enough money Djing and at 28 I value money more than my passion for music where at 21 it was completely the opposite. It may not seem like it if you're on the other side where you work a boring job just for the the bills and wish you can do something you love but years and years of not being paid a lot will slowly strip your passion away. Last week I opened for Kid Capri on turntables (brought my equipment, set up, sound checked) and got 10 percent of what he received. I notice that many of my college friends just have higher quality of lives than myself and many of the people I know within entertainment (even those that I know who tour religiously)
The analogy one of my lawyer friends gave me is that your average dj is like a public defender. lol. Dave Chapelle said on inside the actors studio that he would be okay with making a Teachers salary as a comedian and I was talking to a friend who's a comedian and we both agreed that all the things you have to deal with (and the uncertainty) in entertainment I'd rather just be a teacher on a teacher's salary than an entertainer on one.....basically if I'm going to keep doing this, I need to be well off financially in a position like tv, radio, sponsorships otherwise it's not really worth it & you run the risk of being 40-50 years old grinding for a hundreds of dollars every time you can and being the old man in the club....I'm good.
It also hurts that technology has eliminated the barriers to entry.......basic supply/demand.....has brought everyone's prices down (even some of the top dis in philly will do parties for a few hundred dollars which is gas money or a pair of sneakers today) and things like mixtape where I used to make grip of money off now are given out for free on the net (in the 90s and early 2000s you could EAT if you made a dope mixtape....you saw Juice, DJ GQ charged dude $15 for a party mix of a cassette, now imagine what a nikka like DJ Drama was making off mix tapes.).
I've actually thought about going back to school recently. I'm still figuring it all out.