In my mid 20s I had only a vague idea what I wanted to do, I had few real (read employable) skills and I had never really developed a plan or worked hard at anything. I then spent five summers as a canoe guide in northern Minnesota and Canada. It toughened me up, forced me to plan and take responsibility for myself and others, taught me to think and push my way through challenges, etc., etc. Those summers for me were not "vacations". They were hard work for very little money and they formed me. Perhaps the OP does understand that pushing day after day on a bike is not the same as sitting around home, and perhaps he sees that as the exact kind of thing he needs. It's also sometimes true, and this was certainly the case for me, that people cannot change without getting away from their present situation, their people, their environment. It can be tough to become the person people tell you you cannot be.
I think the foodstamp idea is dumb and wrongheaded. Meeting the girl of your fantasies on some lonely two lane is a pipedream. But jumpstarting your life by following Sheehan's advice to "first be a good animal" is spot on. It's an appropriate place from which to build.