I am gearing up to work abroad as well. I am not not going to bother with a work visa. Because I work remotely I don’t need to work locally. I don’t know what the laws are. Working in a country without a work visa is probably illegal but I don’t see how anyone would catch me. And anyways, I am a tourist and still paying taxes in the U.S.
Here are my tips…
—If you need to rely on your web work to eat while abroad then you should probably wait until you have a steady stream of work. You might want to switch to freelance work full time and build up your business before you leave. If you can’t live off it in the U.S. then you shouldn’t assume you can live off it anywhere else.
—Without a work visa, most people do visa runs. That is, you enter the country a get a tourist visa. The duration of the visa depends on the country but often you can get one for 3 - 6 months. Before the visa expires you leave the country and then re-enter and this renews your visa. Rinse and repeat. Check into the country you want to move to before you go. You might have better options available if you get a visa taken care of in the U.S. first.
—Another option you can look into is languages classes. For instance, I have found schools in Taiwan and Thailand which will give you an education visa (good for as long as you are going to school) which offer classes as short as a couple hours per day and as cheap as $100 - $300 USD per month. Different schools have different prices and schedules. The perk is you learn the language. The negative is that you pay for the classes with time and money but you have to weigh that against time and money spent on doing visa runs.
—Make sure you have a good cushion of savings (like six months of expenses and a plane ticket home.)
—Do all your planning well ahead of time. Consider that moving regularly will be highly time consuming and juggling this with freelance work will be very tricky.
—Or maybe you can just jump in. I don’t know your situation. Maybe you have a trust fund and don’t really have to worry about work. Maybe you can just travel around out of a backpack for a year. Some people just go and find work and everything works out. There are always exceptions to the stories of what you can or cannot do. I prefer more planning though.
—Check out the Location Independent blog for more tips.