Originally Posted by Two Wheeled 'Tard
I've gotten quite a number of PMs about this topic, so I'm going to elaborate more on my post.
To reiterate, the way that I'm able to take a large number of multi-month motorcycle trips is that I do contracting work in very remote locations around the world.
The first thing I need to say is that it's nearly impossible to do this if you have kids; so if you've already reproduced, to you I say "HAHA that was stupid!".
These jobs are usually working for the government in some way (Usually through a defense contractor) and are similar to being in the military, in that you sign on for a specific amount of time. Usually for six months, but some places the contract lengths are two years. And during that time, when you're at the location that you're working, everything is provided; you don't pay for food, housing, transportation, anything. Every dollar you make goes straight into your pocket. And when your contract is done, that's it; you're done. If you want to repeat and come back, you do have to re-apply and re-interview and be re-hired for your job for each contract, but for the most part it's usually pretty easy to be hired back if you've done a good job the first time around.
There's two basic routes to contracting.
The first route is the "Sell your soul, shit-tons of money, might get killed" route. This is either working in war zones such as in Afghanistan and formerly Iraq (that's pretty wound down by now), or working for oil companies on remote drill sites and oil rigs. They will usually require making pretty big moral compromises, or have a significant risk of getting shot at/killed. On top of that, the work experience itself usually sucks; 12 hours a day, 7 days a week is typical, for weeks or months at a time. High stress, everyone always screaming at you to work harder, go faster. The flip side is the pay is insane; front-line war zone jobs can pay upwards of $150,000 for basic work, and I knew one guy making $350,000 a year running network cables in front-line bases. This is largely tax-free, as well.
The second contracting option is the "Awesome experience in crazy locations for low pay". The pay is usually about 1/2 to 2/3 what you'd make hourly in the states, however you're still not paying for anything so as long as you're not trying to maintain a house or family, you can do quite well for yourself. The upside is that you're usually working in really neat places, with really cool people, doing work that you'll hopefully enjoy a lot.
I'm currently taking Option 2, awesome experiences for blah pay. The pay is medieocer at best, but because I save every penny when I'm working, I come out of a contract with a nice chunk of change. And I like the places I work; they're full of vagabonds, part-time workers and full-time travelers. Most of us only work 6 months on/6 months off, saving our money when we work and then traveling for the rest of the year.
I hope that's cleared things up a bit. Good luck getting out there and seeing the world some :)