Canada and England are easy-mode for an American expat, in my experience. In addition to language, there are plenty of US firms already doing business there.

Canada and England are easy-mode for an American expat, in my experience. In addition to language, there are plenty of US firms already doing business there. The easiest way to be an expat, by far, is to work for an American company who then sends you to work overseas. Ideally, an American firm with a large number of overseas US workers and an established program for that -- or a government organization like the State Department, entities like USAID, etc. It's probably easier (in terms of not needing to make any decisions) to work for a US oil company and live on a compound in Saudi Arabia than it is to find your own way in a more permissive country. But less fun, I'm sure.