For a while now I've been contemplating about where to go. No matter where I go, I can't see myself working at the same place for several years, although I felt the same way when I went to Japan and I ended staying there for 5 years. In any case, I've been looking at ways to make my existence more nomadic.
There's three things that are absolutely vital when moving to a new place: finding accommodation, arranging transportation and getting a job. The relationships between these three things are incredibly intricate. Depending on where you go, it may be favorable to find a cheap flight first, and then arrange accommodation. For other destinations the price of a flight may pale in comparison to the monthly rent. And in both cases, if you manage to land a job then you can probably afford to worry a lot less about both accommodation and transportation. But getting a job is a whole lot easier if you're already accommodated in whichever city you're planning to go to. One thing needs the other, yet having one of them might mean having less trouble finding the other two.
The biggest dilemma perhaps is to look for jobs or to look for accommodation. I've been doing a bit of both, and had success with neither. Personally I'd feel more comfortable already being at my destination and then looking for jobs, rather than flying back and forth, landing interviews and hoping for that lucky break. Getting a place to stay first shows my resolve, and it means I can worry about one thing at a time. In my particular case I'm rushing things a bit because I have to be in London in July anyway, but logically it makes more sense to find accommodation first and then booking the flight. In fact, if you look at it that way, I'm doing things in the worst possible order. The best would be to get a job first, have them pay for the flight, then stay in a hotel while arranging long(er)-term accommodation. I got the flight first, now I'm looking for accommodation, and then I'll find a job. Oh well.
More importantly, I've been thinking about the long term sustainability of such a lifestyle. Provided one can find contract jobs that last between 3-6 months (of which there are plenty, it would appear) it should be possible to repeat the same trick later in a different city and country. It would be quite tricky to get a job without a face to face interview, so getting accommodation first would probably be best. But that means you're basically gambling with your life, hoping that the right job opportunity will pop up in front of you in the short time period that you are there. If it doesn't, you could always relocate to another place and repeat. It's just like gambling: if you land a job, you profit. If you don't, you have a nice long holiday in a city you've never been to.
Either way, it's more fun than staying with your parents.