I Was an Expat Freelancer: Lessons Learned the Hard Way

Starr Horne bio photo By Starr Horne

One of the main attractions of freelancing is the mobility. You can - theoretically - work from anywhere.

I was recently lured back to the states to work for a startup in Seattle. But before that, I spent over a year living and traveling in Mexico while working as a web developer for clients in the US.

When I first contemplated taking the leap, I was surprised to find that there wasn’t much practical info to help web developers and other freelancers who want to travel the world. The information that I did find was mostly BS.

So, here you go world. Here’s how to become a globe-trotting freelancer in 28 easy steps:

First: buy a plane ticket

…the non-refundable, non-transferable kind.

There’s never going to be a perfect time to take the plunge. But when you buy a ticket you commit yourself to a date. Personally, my lease expired August 1st, and I flew out August 2nd.

Give yourself a month or two lead time. But more than that and you run the risk of over-thinking it.

Expect to be stressed out for a while

> > Remember, you’re not really alive unless you have a panic attack every now and then. > >

Now that you have your ticket in hand, you’ve probably started to think, “Crap, what am I going to do with the cat?”. Or something similar.

You’ll have a million things to do before you go. You know what they are better than I do. You’ll finish some things, but not others. In the end it won’t matter.

So just take a deep breath, keep a decanter of cognac handy in case you get the vapors, and go for it.

You won’t know what people are saying

Please tell me you didn’t buy a ticket to Australia.

> > Startling Fact: even in this day and age, a majority of countries don’t use English as a first language. > >

Startling Fact: even in this day and age, a majority of countries don’t use English as a first language. First order of business is to get yourself into a language school.

If you can swing it, do a few weeks of 4 hours-a-day intensive study. After this, you will still suck at your chosen language. But you’ll be able to order a taco.

Make friends with the locals

A lot of the spanish schools in Central and South America also offer english classes to the locals. They’ll probably be hanging around in the commons having a lot more fun than you.

Go up and make friends with them. This is how you’ll really learn the language. At least the cuss words.

Also, a lot of immersion language programs will match you up with a host family. Basically you’ll get to stay and share meals with a local family for a reasonable rate (which you will later find out is exorbitant). I had a great experience doing this. Other people I know didn’t care for it. But It’s worth a look.

You are “The Stupid Foreigner”. Get used to it.

> > You will be the crazy japanese guy at the bar singing "bad bad leroy brown" > >

Here’s the key to expat success. You can get away with murder as long as you play the dumb foreigner card. Just smile, say “yes” a lot, and be prepared to sing karaoke.

When you’re in a foreign country, speaking a new language, and learning new customs it is impossible to, say, smoothly ask a girl on a date. Or buy a cup of fruit.

…but people will love you as long as you try. Or at least they’ll tolerate you.

Be safe, but don’t be paranoid.

There’s crime everywhere, so be safe. But also realize that most people are decent and will be kind to you if you’re kind to them. Pay attention to what the locals do, and what they tell you. Pay less attention to the media.

Professional Matters:

A lot of what we’ve discussed covers travel in general. But now I’d like to address a few issues that directly affect freelancers.

  • You won’t bill as many hours.

If you’re expecting to bill 30-40 hours a week, you’re not going to have a good experience. You’ll be working from coffee shops. You’ll have language class. You’ll be hung over (FYI: in every country except the US, people seem to go dancing every night of the week)

When I was settling in, I was only able to do about 10 hours a week. After a while that moved up to 20.

  • Your hourly rate may go down. If you’re from a tech hub like Seattle, working for local companies, you can bill premium rates. When you have to find work remotely, the projects don’t seem to be as lucrative. Fortunately, this will be offset by the fact that your guest country has a lower cost of living. (You didn’t buy a ticket to France, did you?)

  • You can access the internet from anywhere these days. But the connection may not be the best. Expats use Skype a lot, but the quality may not be good enough for business calls. Also some ISPs block skype, because they are also the telephone company. Welcome to a world without anti-monopoly laws.

  • Your travel plans will be dictated by immigration law. Chances are, you’ll be in your guest country under a tourist visa. These usually state that you can only be in the country for a certain number of days per year. In Mexico, it’s 6 months. In other countries, it’s 45 days. This means you’ll have to cross the border periodically.

Don’t even think about trying to get a work visa unless you plan on working full time for a local company.

  • Keep all of your bank accounts in the US, and keep your US cell phone. Online banking is awesome. And ATMs are everywhere. Also, your phone company may have a special plan to let you use your US phone in your guest country. (AT&T has a Viva Mexico plan)

  • Be aware of time zones. This is a good reason for travelers from the US to explore Central and South America. The timezones are similar to US timezones. So you won’t have to take client calls at 4am.

  • Pack Light. Take any electronics you need. You’d be surprised how little you need. For my initial trip to Guadalajara, I lived out of a single carry-on. (containing my Macbook, Kindle, phone, toothbrush and a few changes of clothes)

Clothes and toiletries are usually cheaper than in the US. Electronics can be up to 5 times more expensive. Seriously.


I hope this article would have been useful to me, 2 years ago. Everything I’ve said has been based on my own experiences in Mexico. But the world is a large and wondrous place, so it wouldn’t surprise me to learn that things are different in Cambodia, or the Czech Republic. I’d be interested to hear if they are.