Freelancing in South America for 8 Years; Things She’d Do Differently

In 2016, I spent two weeks in Medellín, Colombia — and it changed the course of my life.

I explored the city and hiked to a waterfall hidden in the mountains, but it was the small details that stayed with me: Latin music I’d never heard before, tropical fruits, and locals socializing in a neighborhood barbershop.

Back in Canada, I couldn’t shake Colombia’s beauty. I hatched a far-fetched plan: become a freelance writer and move there.

At the time, I was in my mid-20s, living in Toronto, and working in magazines. With no deep roots in the city and a sense I’d soon be changing jobs anyway, the timing felt as good as it would ever be.

Over the next two years, I built up contacts, clients, and savings. Then I returned to Colombia to go freelance. I wanted to immerse myself in the culture and learn the language.

Eight years later, I live in Ecuador and still work as a freelance writer. The move worked out — but there are a few things I’d do differently.

Here’s what worked

I researched the monthly cost of living and saved for a year

Creative industries like mine can be unstable, and there’s always a new hurdle. Right now, it’s AI.

The instability and oversaturated market can keep people like me from giving it an honest shot. Knowing I had my work cut out for me, I saved enough to cover my living expenses for a year, about $8,850.

I was halfway there already and saved the rest by freelance writing in the evenings and on weekends and by simplifying my lifestyle. I’d been working full-time for a few years as an editor at a running magazine in Toronto. The savings goal was pretty straightforward: 1,000 Canadian dollars a month for the time I planned to be away.

When I got to Colombia, I was fortunate to work while exploring the rolling green coffee region. Oftentimes, I hiked through fields after meeting morning deadlines. I was slowly figuring out how to lean into work that felt satisfying and valuable. It didn’t take long to come up with the three client green flags I still stand by.

Those are: a client that’s enjoyable to work with; work that’s meaningful and engaging; projects that pay well. In deciding whether to accept new work or continue with existing contracts, it has to be all three.

In hindsight, there are things I’d do differently

Of course, hindsight is 20-20. For anyone on a similar trajectory, this is what I’d do differently.

1. Dedicate time to learning Spanish and nothing else

I now speak Spanish at an intermediate level, and my second language has been crucial to my work. Because I write travel stories largely set in Ecuador, most of the pieces I’ve published have either been inspired by a conversation I had or required interviews in Spanish. Oftentimes, it’s both.

When I arrived in South America, I didn’t expect to stay this long. I enrolled in Spanish classes right away — and I’m still studying — but in hindsight, I would have learned faster if I’d paused everything else and focused solely on the language for a while.

2. Give back to my community more

Remote workers like me are part of a relatively new and deeply privileged group that can work in one economy while spending in another. That reality has never sat comfortably with me. It’s my opinion that those of us in this position — myself included — owe more to the communities we live in.

After all, in the absence of an office, my neighborhood has become my workplace. Though I’ve given back in small ways, one thing I’d do differently is commit to supporting local causes close to my heart on an ongoing basis, whether through my time or money, or both.

3. Put myself out there

Last year, I realized I’d been standing in my own way. For years, I’d refused to put together a proper online portfolio. When I finally did, several opportunities came up — including a large travel writing project.

That editor had been on my radar but when she came to me, I realized I’d underestimated myself by not making the introduction first.

So, in retrospect, I’d put myself out there by launching the website, sharing my work, or getting in touch with goal publications without hesitating.

4. Take advantage of freelancer flexibility

There’s a lot that freelance work and entrepreneurship don’t offer: stability, paid sick days, benefits, the safety net of HR — I could go on.

What it has offered me is freedom and flexibility — and that’s what has made it worth it. Nobody can tell me when, where, or how to work.

Looking back, I value how hard I hustled, especially during the six months when I lived in Medellin. I’d tell that younger version of myself to lean into that flexibility a little more and travel solo.

That trip I took 10 years ago inspired a dream that eventually became a plan. That plan was shaky at best, but a decade later, I’m now in my mid-30s, living in a part of the world I love with a writing career I’m happy with.

Do you have a story to share about living abroad? Contact the editor at [email protected].