Listen, after 12 years of being a resident something at regional theaters, jumping into the freelance world at the age of 40 was simply the best career/life decision I could have made.  All of a sudden I was able to pick and choose projects based on my wants, needs, career goals.  Yes, my pocket book hurt for a bit . . . but I think I have sort of ended up okay.  You need to bet big to win big.