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, ranging from a contraction of the words "Hoe Boys" to one from 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.