Taking Chances: My Take on Risk Assessment

I used to work in a bar/restaurant for extra income. I made cash in hand that complemented my salary, and they fed me 3 times a week. I could afford to buy my lunch and was still saving money. It was pretty good.
Today I work one job. I volunteer, I'm active in a few professional organizations, I'm taking a class, I run almost everyday, I'm starting a business, I write this blog...and I am flat broke.
I have to be honest, living month to month is kind of a scary thing, especially with imminent expenses looming (graduate school anyone?). However, leaving the restaurant was the best thing I could ever do for my career. I freed up 20+ prime hours of my day to network, learn new skills, and seek out opportunities. Giving up my extra income was a risk I couldn't afford NOT to take.
I'm on the verge of taking a few more chances (in spite of the costs of a dentist appointment I know I need to make). But before I deplete my savings account I had to ask myself: Can I afford to NOT take this chance?