The main thing to think about is this: do you want a one-time, round-the-world experience, or do you want this as a lifestyle, say working 6-8 months a year and traveling the rest?
If you are like me and want the latter, then become a contractor and specialise in something that pays well (for me, J2EE - not a great technology, but Big Corp Inc. pays well for these skills).
The OP seems to suggest a work/travel approach, but to be honest I found that can be tough to sustain. To be maximally productive, it's really helpful to have comfortable and familiar surroundings, very solid internet, etc. I tend to do just-for-fun coding on trips instead, since I found trying to get setup in new places to be stressful.
The only problem I've found is that contracting gigs don't pay well and usually want you onsite. I've got 12+ years as a JEE dev and make a decent salary at a big corp but all of the contracting companies out there only want to pay you $50-$55/hr which isn't even close enough to being enough.
Are there any books or something about how this contracting thing works? I'm just about to start my career in programming, and I don't really have a hang of the business side of things -- not hoping for a quick change to contracting, but I'd like to start to understand how it works.
E.g., what kind/level of J2EE expertise do you need to become a solo contractor for Big Corp Inc.?
As a contractor, do you work on a project in a company office for X months and then leave? Or do you work from home? Etc.
1. Worked for around eight years as an employee at a few places, including a couple of startups. Ended up with a lot of Java experience.
2. Realised I wanted to restructure my life to work less (but still make good money) and travel/have fun.
3. Spoke to various people and found that contracting through a consulting company (not recruiters, but a team of like-minded programmers) was the way to go, rather than pounding the pavement to look for contracts. The company takes its cut, but I still end up with $80-$95/hr, and they find the work for me.
As for experience: Big Corp Inc. wants contractors who can get up to speed very quickly. You tend to get pigeonholed based on technology, so if you get the assignment as a "J2EE guy" and you don't have a lot of experience, then you look pretty dumb. Spend time working as a normal employee first and really become a good programmer.
As for work duration: generally, the contracts are open-ended and I am terminated when a project gets cancelled or whatever.
I specify up front that I will spend the bulk of my time working from home and that I am taking holidays from time x to time y. The company that subcontracts me out is based in Silicon Valley, as is Big Corp and friends, and I live in western Canada, so this isn't usually an issue. I fly down once in while to hang out.
So to sum up: get experience - learn to be a good programmer who has a reputation for getting things done; learn what big companies want in terms of technology; find a company with good connections who will contract you out, possibly as a team with other people; be up front about your lifestyle but work hard to integrate with their project schedules.
I think there are plenty of software consulting groups around, particularly in the Valley. Google is your friend on this one, or if you're a local, just ask around.
I was referred to the company I now work with most, but I found the last bunch of guys I was with via Craigslist.
I did the work/travel thing for 14 months and found it ok. I wouldn't want to commit to more than 15-20 hours work per week whilst travelling though.
My plan for the next trip is to travel in between contracts and then settle down for a few months at a time whilst working. Hopefully that will allow more focus.
Edit: Actually I like gexla' idea above - pick a comfortable home base to work in and travel to nearby areas/countries in between contracts.
If you are like me and want the latter, then become a contractor and specialise in something that pays well (for me, J2EE - not a great technology, but Big Corp Inc. pays well for these skills).
The OP seems to suggest a work/travel approach, but to be honest I found that can be tough to sustain. To be maximally productive, it's really helpful to have comfortable and familiar surroundings, very solid internet, etc. I tend to do just-for-fun coding on trips instead, since I found trying to get setup in new places to be stressful.