The web hobo

web-hoboWhat a glorious time to be a hobo! I’m not talking about the historical train-jumping vagrants who slung sticks ‘n sacks over their backs. Instead, I’m referring to web hobos — those among us with the enviable ability to be on permanent vacations through the power of connectivity. When you can work from anywhere, anytime, life can be a delicious treat indeed.

While I don’t necessarily spend my days traveling the world (two young children at home keep me relatively grounded), it is fair to say that I do occasionally take the mid-week trek to new and exciting places. The business model is simple: I start work at 6 a.m., work until 2 or 3 p.m., then spend the rest of the day sight-seeing, exploring a museum, taking in the zoo or lounging poolside.

Some people take it to the extreme, spending much of the year on the road. Perhaps you’ve heard of Tim Ferriss? He calls his vacations “mini-retirements” and spends them in exotic lands such as Buenos Aires and Thailand. Laptops, cell phones, blackberries, and the connectivity afforded by the Internet have made it possible to enjoy an enriched lifestyle without having to be a millionaire. After all, no one wants to be a millionaire simply to own a lot of dollars — we want to be millionaires because the status promises an extraordinary lifestyle.

The modern hobo has traded in his bindle stick for a laptop carrying case, given up begging for comfortable accommodations and cultural cuisine, and travels for pleasure and not out of necessity. Anyone with a skill that can be sold remotely can enjoy the life of the web hobo, even if only for a few days each year. Writing, design, and development are three such skills; but there are many other professions such as virtual assistance and online retail sales that can facilitate the “good life.” You don’t have to freelance, either. Some firms will allow employees to take working vacations as long as production isn’t compromised.

Tell me — is the hobo life for you?

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