I focus on restaurants. I currently play almost every night of the week and twice on Sundays, with private parties, weddings, receptions and odd gigs in between. Long ago I purposely moved to an area with a high percentage of restaraunts and upscale lounges to establish my market, and I've worked other jobs on the side until I built my clientel to the full-time levels it is at now.

I found that the way to generate income is to work the room, not just play it. I use my breaks to meet/greet people, pass out song lists and take requests (in other words, I really don't take breaks). Between tips and CD sales I can generate an additional 25-50% over what my client pays me. Not only that but once you makes freinds with people, even in the short term, they will follow you from place to place which is known as a "following" - which gets you rehired.

You have to plan for going solo financially by reducing your debts/bills to low levels and building savings for lean times and unexpected gig cancellations. Having a supportive and employed spouse doesn't hurt either.

You've got to really want to do it with all your heart. It shows, and you'll get support from the audience if you can convince them that you are a full-time muso because you should be.