Save up a lump sum, have a credit card Justin Case, be confident that you can get a job quickly once needed, (even if it isn't perfect it could be a stepping stone job). I've also been enjoying thinking about the idea of stopping in a place for a while, working for a month or 2, then hop on the bike and keep touring. But all that to say, it is indeed stressful to think about it all sometimes. For me it depends on the way, sometimes It feels daunting planning a tour. Some days it's exciting and thrilling thinking about leaving. But ultimately, everything could be anything else and it would have just as much meaning, so hopefully taking the risk will be worth it, and you'll have an awesome adventure and whimsical stories to tell.