You remind me of a coworker I had four a couple of years. He and his wife were both extremely competent and well-compensated programmers. Their lifestyle was basically "work for two years or so, save up a bunch of money, then quit and wander the world doing whatever they liked until the money ran out, repeat." I've thought about them several times. Some part of me is really, really uncomfortable intentionally living off of my savings for a prolonged period, but I also sometimes wonder if they haven't figured out something important that I haven't.