5/8/12 update: I'm going to open this up as an alternative q&a thread on travel tips / being an expat / remote-work / lifestyle design / etc. Feel free to ask away, i'll do my best to answer q's as quickly as I can.
My experience: Have lived in China (8 months), and now reside in Buenos Aires (15 months). I've traveled through central and south america, china, thailand, turkey/greece, and france/italy/spain, and studied up/heard stories on numerous other places. I work remotely from Buenos Aires as the COO for wallstreetoasis.com
I've been asked a lot about this lately so I finally got motivated to put my story into words
First i was motivated by this post earlier today:
TheKing wrote: I'm probably in the minority, but I've always thought the idea of working abroad was overrated. People tend to romanticize things when they are done "abroad." After a few months, it would lose it's luster.
I responded with:
Living abroad isn't for everyone. for me its been a dream of mine to have location/time freedom, and luckily have been able to do this by always having remote work positions (as I currently do). I love traveling/being an expat, have been living in Buenos Aires for 13 months, and wouldn't change it for a second. Hope to keep moving around the world for the next 5-7 years, from here->colombia->europe->asia, & then who knows :)
Which inspired a user to ask this:
Just out of curiosity, what do you do that lets you travel around? I feel chained to my current location and schedule, and I don't like it. Short term, whatever, no big deal, but for the long term I'm looking around at options (including accountant, it's that bad) where I'll have some kind of flexibility. what say you?
Then here was my overly in-depth answer:
Hey, after realizing i could never work in a cubicle/corporate atmosphere the rest of my life after interning at an ad agency (every day I felt like i was slowly dying) I moved to china and taught english after college for ~8 months. This opened my eyes to the idea of living abraod/being an expat/world travel and how much I enjoyed it.
I moved back to the states after a 6 week trip to Europe but promised myself that as soon as possible I would live overseas again soon. So I got back and worked for some online stores doing internet marketing and ecommerce to save up money and get ideas. Flexible schedule, but I still needed to meet in person with the clients several times per week. I traveled some (middle east, argentina, and central america) to satisfy my hunger (3-5 weeks per year) but it still wasn't enough.
Several years went by and I knew i wanted to travel the world a lot more (when you know, you know, its all i could think about when I was working in Seattle) but didn't want to teach english again so I decided to find a career I could do from anywhere. Because of my background and current experience I decided to enhance my skills in internet marketing via certification courses (http://www.tech.ubc.ca/webanalytics) & (http://www.usanfranonline.com/online-certificates/...) and interned at a startup (imagekind.com).
I left the states in oct of 2010 for Buenos Aires w/ 6k in savings and ~$700 per month of income from a very part-time ecommerce job i still had that agreed to let me do it abroad. I knew I would do whatever it would take to be able to work online and live wherever even if it spent living in Bolivia on $5/day for 6months looking for something/networking/studying more about internet marketing.
For approx 9 months after I left the states I traveled / worked the part-time job / studied / applied to online jobs while living down here in Buenos Aires. Then last July I met Patrick through a mutual friend and he mentioned he was looking for someone to help with seo/link-building/marketing.
I'd met several website owners like this before but nothing had yet to pan out. He friended me on facebook the next day and we met at his home office the following monday and went over the initial project. Now it's grown to be a full-time position doing marketing / biz-dev / managing campus reps / license deals with Universities / etc and i've been having a great time doing it.
Lifestyle-wise - wouldnt trade it for anything. I currently work from my home-office in an apt in a fun area of Buenos Aires (Palermo soho), and as long as the work gets done all is well. It's the middle of summer, having a great time, good group of local and expat friends to spend time with, last weekend went to a carnaval event, couple weeks ago went to watch a polo match (didnt even know they still played polo in the world?), in a couple weekends doing a beach roadtrip, play on an american baseball team here, and currently planning a trip to to Bolivia/Peru/Ecuador/ jungle in July.
So specifically for you (or whoever has dreams of working remotely and having time/location freedom), I would recommend finding a specialization in something, marketing yourself (via your own site/linked-in/personal network), slowly building a client base that gives you referrals. A huge thing you can offer to clients is that you can charge a bit less in exchange for the increased freedom (ie happiness), which you are able to do because your cost of living will likely be lower, your productivity will likely be higher (because youre livign your dream right?), and the roi for the client is higher because you're an independent contractor so a. they don't need to pay your overhead, ie vacation / health insurance desk space etc
All in all, the most important thing is setting a date and buying that one-way plane ticket, it will give you the biggest motivation rush of your life (what to do / where to go / how to prepare / etc)
Resources: I think the blog/podcast http://www.lifestylebusinesspodcast.com/ was really helpful/motivating in getting me to do this. Same with 4hww, http://internetbusinessmastery.com/ and http://locationindependent.com/
Based on all the stories i've heard from other travelers, here's my list of places I want to live* for 3-6mo each during these 5-7 years: (*with lots of travel in between these spots). I won't make it to all - but if I can at least make it to half i'll be more than satisfied.
Buenos Aires (currently)
Southern Brazil (Lagoa, Florianopolis)
Medellin, Colombia w/ monthly trips to Colombia's beaches (ie Tayrona)
Boat from Colombia to Panama (with a stop in the San Blas islands on the way)
Bay Islands, Honduras
Spain on the Mediterranean
Yacht w/ wifi cruising the Aegean Sea (Turkey/Greece)
Tel Aviv, Israel
Koa Samui, Thailand
Byron Bay, Australia
China again: Shanghai, Chengdu, Urumqi, & Guilin
Trans-Siberian railway (if it has wifi?) from Beijing to Europe
+ always keeping my ears open for more