To be honest, going the startup route is about the worst possible way to get what you want (assuming you mean: working for other people's startups. Your own co

To be honest, going the startup route is about the worst possible way to get what you want (assuming you mean: working for other people's startups. Your own could be ok depending on how you do it). A startup will likely have stupid ideas about work ethic and they'll probably want to push your compensation into equity. For any startup you join, be realistic, it will not be the next google/facebook. You'll be doing well if it doesn't end up failing. If it does survive, the equity you got will probably be devaluated somehow. There may be some lottery-level chance of becoming financially independent, but you'll save yourself effort by just working a TPS-land job and buying actual lottery tickets. A much more consistent approach would be to contract (or consult if you have the chance) and live frugally. With this, you should be able to save up enough money to take a year off every few years.