I don't think we can judge because we haven't been in the OP's shoes. We don't know what's happened in his life. He could be a war vet for all we know that has had a hard time adapting to the civilian world, or a victim of the housing bubble, and made bad investments when Wall Street took a dive. Lots of people lost their jobs during that time. I don't think food stamps are the answer. Maybe find a cause you are interested in, and take donations to support your ride for that cause. Good luck to the OP, I say go for it if it makes you happy, but definitely get your resume out there and bring your phone with you. For all we know he's trying to get a job but has had no luck. Good luck and have a good tour.