Historically, many people have been forced into becoming hobos because of circumstances where jobs are so scarce that they have no choice but to travel from place to place in search of work. There are many theories of the origin of the word hobo (see Wikipedia's entry, listed in the Sources and Citations), ranging from a contraction of the words "Hoe Boys" to one of the words "Homeward Bound". In any case, the American Heritage Dictionary defines a hobo as "one who wanders from place to place without a permanent home or a means of livelihood." But the dawn of the Internet and increased dissatisfaction with the 9 to 5 routine have led more and more people to wonder if earning a living while on the road is a viable alternative to the daily grind. If you're thinking about becoming an opportunistic and resourceful transient worker, keeping your costs low, your responsibilities simple, and your freedom intact, here are the questions you'll need to ask yourself, and the preparations you'll need to make.
Remember the differences between hobos, tramps, and bums: hobos' are people who travel and look for work, tramps are people who travel and don't look for work, bums are people who neither travel nor look for work.
Farm hand - If you've ever thought about being a farmhand there are places all over the world that offer housing, food, a stipend, and experience, in exchange for getting your hands dirty. You can follow harvest seasons around the country or maybe around the globe.
Take stock of your skills and experience. Historically, hobos have made a living through manual labor, but that doesn't always have to be the case. Any skill that is in wide demand and does not require an extended time commitment can be useful to a hobo. As long as you can advertise your services and earn people's trust (ideally through references), you can do anything.
Establish Plan B. This is a serious, life-altering decision. Don't abandon everything suddenly and disappear. You need something to come back to if your life on the road doesn't work out. Make sure all your debts are paid and responsibilities are handled before departure. If possible, have some savings set aside before you go, that you can access while you're on the road, if need be. Emergencies happen, and they cost money.
Be prepared. You may like the romantic idea of leaving with nothing but the clothes on your back and whatever is in your wallet, but that is a sure-fire recipe for disaster. You must assume that you will be sleeping, cooking, traveling, and essentially living outdoors, unless you decide to drive a car
Make a list of connections. Look at maps of the areas in which you'll be traveling, and determine whether or not there's anyone you know, directly or indirectly, who lives there. Ask your Aunt Sally if your great uncle Billy still lives in that cabin in the woods. Ask your friend if his cousin still works at the car dealership in Utah. Most important of all, ask them if it's okay if you can get in touch with those people in case of an emergency. Some people might offer to make arrangements so that you can actually visit, which is always nice. (Just be a good house guest!)
Make an itinerary based on the type of work you plan to do, the connections you have in place, and the places you'd like to see. Do as much research as you can beforehand. Make a list of places you can stay, eat, shower, camp, etc. It's also wise to look up churches and shelters and any services that are offered to the homeless. The more prepared you are, the more you'll enjoy your travels.
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