How do I get to a point where I am living off of my passion?

Sometimes makeup is the only thing that brightens my day. There is so much to be thankful for, don't get me wrong, but I work at a job that is not fulfilling. It didn't start off that way. I work in higher education for a grant funded program called Upward Bound. My students are usually the highlight of a boring day, but lately even their smiling faces hasn't been enough to keep me interested in my work. This may be due to the numerous problems I've been having in the workplace since November 2010. Also, in the summer time I don't get to see the students during the last two weeks of July and the whole month of August unless they are coming in for a brief visit. I'm going on the 2nd week of kid withdrawal. So today, like the last couple of weeks, I'm feeling a bit underwhelmed. I want so much more out of life and although I have a Masters degree in Education: College Student Affairs, I feel a sense of gravitation towards makeup. It's my passion and every morning I wake up and want to paint faces or write about how to paint faces.

I'm looking for my utopia, a place where I can let my creativity run wild. Right now there's no balance in my life. I have a steady pay check, but I'm paying a steep price of that in makeup time and blogging time. How much sense would it make for me to up and quit my "semi-secure" job (so not true for grant salaried workers) to be a freelance makeup artist or makeup counter artist or even a beauty blogger... Probably not a whole lot, right? I guess I'm in need of some encouragement and direction. How do I get to a point where I am living off of my passion? How do I reach for a dream without taking too much of a risk. And I'm so tired of self-help books that don't offer tangible solutions... The idea of trusting myself, hard work and talent to provide a steady income every month that covers my mortgage and bills is scary to me, right now. If I jump from one career to the next, is there a safety net to catch me if I fall short of reaching the other side? Leave your thoughts in the comments section.

As you can see, I don't have all of the answers. I can't tell you how to become a full-time makeup artist so that you can quit your crappy job... I'm still trying to figure that one out. BUT what I can promise, is that if I figure it out, I will happily pass that information your way.