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Thanks for the write-up! I am a junior in college who is very interested in that sort of lifestyle when I graduate and finish off my student loans. I'd be happy as a clam if I could find a job or a number of freelance projects that'd allow me to have a decent standard of living abroad while seeing different parts of the world. I have a few questions if you would be so kind to consider.

Are you considering trips anywhere else? How is your Spanish after spending a year in Mexico? What was your relative standard of living like when making money from these projects? Did you go into it with a reasonable "war chest" of savings to live off of while acclimating to the environment? Was it ever a deterrent to potential hirers that you were abroad? What was the coolest part of your experience?

I might have a couple more depending on your answers.

Hi, I'm glad you found the write-up helpful. Feel free to email me if you have any questions. (my email address is in my blog header).

At the moment I'm not planning any more trips. I took a job with a startup in Seattle, and so I'll be here for a few more years. After that, who knows :)

You don't need much of a war chest if you go to the right places & have a decent amount of work. In guadalajara (a big city), $1k / month will get you full-time spanish lessons plus room and board. Hostels are about $12/night if you want to go that route.

My standard of living was very good. I had a 2 bedroom house in the trendy part of the city. Ate out whenever I wanted. etc. I imagine I was spending 20k a year (not including state-side expenses such as student loans).

My spanish is pretty good. You learn survival spanish pretty quickly. After a year I'm able to hold conversations, understand song lyrics, etc...more or less :)

I don't think I lost any clients from being in mexico. It was win-win. They got a good developer at a slight discount. I got my mobility. Actually, about 1/2 of my existing clients never knew I was in mexico. I didn't hide it from them, but it never came up.

Coolest part: making a lot of friends from around the world.

I tried something similar this past summer while traveling through Europe/Turkey and found that the hardest part freelancing (beyond the difference in time zones) was finding stable wifi in order to transfer client files. Even in a place like London I found myself in train station Starbucks uploading files.

I imagine if you stayed in a country for a while it'd be easier to get mobile broadband but hopping around a continent makes it pretty difficult since you can't (in my experience) get sim cards with data plans and use them in several countries.

Hmm, I don't have much experience with working while traveling through lots of countries. I can imagine that does make it harder. Though, to be honest I did do most of my work from a Starbucks. Even went on a date with one of the baristas. :)
I have been an 'expat freelancer', local employee, student, local entrepreneur, and an expat full time remote worker (present status) in a handful of countries on three continents.

The main points I'd say are: things change, everywhere's different, and have patience. With many passports in many parts of the world you can border-hop as a 'tourist' quite comfortably, essentially living for arbitrary amounts of time wherever you please. This is really great, but can be a bit draining.

The hardest things tend to be social needs, language, food, expectations of folks back home, and the cost of relatively long distance flights. Also, you need motivation: it's easy to get lazy.

Great side effects of long term living abroad: new languages, meeting cool people and sexy potential significant others, great food, lower overheads, cheap medical care (who needs medical insurance when a serious operation is a mere fraction of the price of back home?), less government crap (licenses, insurance, etc.), often less tax.

Some banks have excellent expat-oriented services (eg: HSBC) that are worth looking into if you're going long term.

Not for the risk averse, the timid, or the mortgaged.