[ddavidn]

I think if you have the drive to become an entrepreneur, you will. My experience, really quickly, is: Intern programmer, two years college, two years working, one year entrepreneur, at my current job for three years. I spent one year doing freelance consulting and development, and it was a blast. I had fun, but didn't make quite enough money to live on, and found a job I was happy with. I freelance on the side now. But I'd do it full-time again in a heartbeat if I could save up some money and line up some steady monthly work. I don't think starting your own business is everyone's plan. From how you're presenting things, I personally think it's very likely that you will leave the "comfort zone" you mentioned. My reasoning: It won't be your comfort zone. I've never felt comfortable just doing a 40-hour week, and I think that underlying entrepreneurial spirit keeps me from being comfortable with the mediocre and ordinary (which my job isn't).

I also hang out with a couple people that bootstrapped their own product/service while working a full-time development job and they now run successful businesses by themselves, after running it "on the side" for 1-2 years.