I wrote a version of this article that made me sound like an expert, but it felt like a lie, so here’s the real dirt:

Packing up my life and moving to another country to do remote, online, freelance work is the hardest thing I’ve ever done in my whole life. And I’ve worked in customer service.

If you’re seriously considering blowing this provincial popsicle stand in favour of the tumbleweed life, you already know it’s not as simple as quitting your day job and hopping on a plane. It’s a genuine, every-day, slog.

But as long as I can afford to eat, I’ll still be trying to build my writing career outside of the U.S. Why? Because Spain feels like home now. And because I’m actually making some progress. It’s slow, but it’s real. At this point, it feels like a game, and I have this insane compulsion to keep beating the next boss. (That’s a metaphor, don’t beat your boss.)

Luckily for you, I’ve been playing this game long enough that I can share some cheat codes – and that’s an achievement in itself.

Cheat Code 1:

To Nomad Or Not To Nomad.

I don’t usually call myself a digital nomad because it sounds like something out of The Matrix, but there are certainly comparisons to be made:

Unplug yourself from your current reality? Check.

Learn new skills as fast as humanly possible? Check.

Suddenly become uncomfortably aware of the fallacies of your own culture? Check.

Become “The One” that you and others rely on to get stuff done and make important changes? Check.

When you pack up your whole life and move to another country to become a start-up of One and support yourself with digital, remote, freelance work – you’ve taken the red pill. There’s no going back.

When people start freelancing and getting comfortable with a job that requires nothing but a computer and their own expertise, they can sometimes decide to take their act on the road. 3 months in Italy, 3 months in Morocco, 3 months in Germany, etc.

I personally don’t understand how people do that. Maybe it’s the Taurus in me, but I need some stability in my life. I took a different route.

I got a long-term visa to live in Spain because the cost of living here is cheap (my rent went from $1300/month in San Francisco to $400/month in Barcelona). From here, I can buy plane or high-speed rail tickets to tons of places in Europe or Africa and spend a long weekend.

Here’s why I feel this is the better route-

  • I feel grounded, but I still get to travel regularly.
  • I never run the risk of overstaying my visa somewhere.
  • I never run the risk of running out of money trying to live in a much more expensive country (On a Switzerland budget of one chocolate truffle a day, you’ll be broke in approximately two days.)

Cheat Code 2:

Full Disclosure – I Aspire To An Office Job

I get that the reason you’re thinking about making a go of it on your own is because office life sucks. The open-plan experiment needs to die before someone murders a coworker for chewing too loud and interoffice politics can drive you bonkers. Not to mention the long hours, the measly benefits, and the lack of upward mobility.

But have you considered that office life in another country may be better?

My Spanish boyfriend works at a data consulting firm here in Barcelona and gets 22 paid vacation days a year. That’s not the company, that’s the law. He also gets 14 paid public holidays, Friday afternoons off, and every afternoon in August off (because of the heat). If we want to have kids after 2021, when a new equal rights law goes into effect, he’ll get 16 full weeks of paid paternity leave. (Moms will get the same amount, obviously.)

Am I saying you should move to a new country just to get another office job there? Not at all. I’m saying that it’s going to take you a while, maybe years, to be able to give yourself the kind of benefits some countries’ governments are smart enough to know should be your right as a human being. It’s going to take a lot of patience and hard work to get to that point in your freelance career, but I believe in you.

Cheat Code 3:

Life’s A Beach And A Box.

I love the freedom I have. I make my own schedule, I manage myself, and if I answer to anyone besides myself, at least it’s only through email. And, yeah, I travel. My Instagram page is the bomb and my world feels so much bigger these days.

But I had to let go of so many ideas about what I thought this was going to be like. You know that image you have of working on the beach whilst sipping a margarita? Not a thing. Trust me, I tried it. It’s far too distracting of an environment. Same goes for that Parisian cafe. It’s too easy to sit there and people-watch.

If you think a digital nomad life is about working in new and exciting locations, I’ve got nuanced news for you – It’s about finding a quiet, boring place within that exciting location to get your work done as efficiently as possible so you might have a shot at coming out into the light on weekends.

You learn to crack the whip on yourself because nobody’s paying you to show up anymore. They’re paying you based solely on your production output.

I work at home, where I do 90-min blocks of deep, focused work throughout the day. During those 90-min blocks, my phone’s turned off, my email notifications are turned off, I close all social media tabs, and I produce, honey. I learned this from Cal Newport’s book, Deep Work: Rules for Focused Success in a Distracted World. That book may have saved my life.

In the end, a digital nomad life is all about self-growth. It’s about serving the part of you that wants a lush life. It’s important to know, however, that it’s going to take planning and drive and a lot of trial-and-error. Unless you come from money or you’ve already established yourself in the freelance world, there’s a lot at stake in this game. So far, though, I don’t regret playing. And if you need some encouragement or advice, I’m always here.

Unless my phone’s turned off.

Or I’m at the beach.


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