Hi Jeff,
I’m all for jumping into the deep end of the pool. I’ve done it myself a few times. Self-employment is rough. It’s hard work and there are administrative tasks and new skills to learn — bookkeeping, sales and more. If you can work your 20-30 hour job, you still have time in the week to develop your business. I’d suggest you slug it out at the grocery store, and put in the extra time to chase your dream.
When you do Tavern work, approach it the same as you would a real job. Punch the clock, don’t mess around with trivial tasks. Everything you do in that time should somehow advance your business development.
There’s also the option of finding a job you like better. Polish up your resume and pass it around. Having a resume — even going through the exercise of self-evaluation when writing it — helps the self-employment cause.
Think about what could possibly be on your plate: self-employment, new marriage, new home, questionable income. I think you have to make sure your home life is solid before you can go into business full-time.