Disclaimer: I created this alter ego so that what I say under this persona cannot be attributed to the me you all know and love (or not). Here's the story: I am in my late 20's and I have a secure job with a high salary ($200K+). I also live in an expensive part of the country. However, I, like many of my colleagues, hate the job. Hint: finance / legal. I've been at it for a few years and over time, my perspective towards life has changed drastically. I used to be driven by money, desire for success, etc. Now I recognize there's more to life than I thought. I realized that I was slowing becoming someone I didn't like. While I had been thinking of quitting for awhile, I was able to overcome my mental hurdle this summer and finally decide to do it. Since then, I have been actively brainstorming ideas for new businesses. However, I soon realized that most of my ideas either (1) required more capital than I was willing to lay on the line or (2) did not pique too much of an interest. I was discouraged until I thought of software development. As long as I'm not doing it for someone else, I think I could do it long term. Also, it is easier for a single person to develop for smaller platforms, like mobile phones or the web. The cherry is that this "business" does not require any capital outlay at all. I don't expect to make much money, so I will be living off my savings. I will have $200K in cash and $100K in retirement money when I plan to leave. Fortunately, no debt. I figure I could get a roommate to save money and more importantly for the social aspect. My lifestyle will not take a huge hit -- rent and eating out will be the biggest cuts. Barring significant inflation, I could live off my savings for 8 years. I could even try to make some money on the side. But man, I would be giving up a toooon of opportunity cost. At least a few million, unless I miraculously hit the jackpot. But, if not now, when will I ever get to throw caution to the wind? I'm not sure of my chances, but I am fairly confident that if this gig does not work out, I can work at a company for slightly less pay than I am getting now. But I am not 100% sure. Has anyone done this before? Thrown away a successful and high-paying job to chase freedom or a fantasy? Am I overreacting and should I tough it out?