5 SHOCKING things I’ve learned from 3 years in Latin America

TL;DR — Expat life in Latin America is not all positive. From cost of living to bureaucracy to taxes, these are 5 things most travel gurus won't tell you.

Rose colored glasses are off.
The honeymoon is over.
And I’m able to reflect on my 3 year experiment in Latin America with a clear perspective.

Contrary to what you may have thought (I’m partly to blame), life here is not all sunshine and rainbows. Here are 5 things that you may not have heard me say publicly, but that may surprise you about Latin America:

1. If poverty bothers you, Latin America is not the place to be

Latin America has some of the most inequality I’ve ever seen in my travels around the world. And I have the data to back it up: Colombia 🇨🇴 is one of the most unequal societies in the world.

World inequality map

Now, this is not inherently such a negative thing. Depending on which city you’re in, you can live in more well-off or touristic neighborhoods and not witness poverty every day. Out of sight, out of mind.

But that doesn’t mean it doesn’t exist around you.

If living amongst poverty and seeing it every day does not bother you, then by all means. Mark this off your list of reasons not to come to Latin America.

2. Cost of living depends entirely on your lifestyle

Let me preface this by saying cost of living is 100% relative. What’s expensive to you may be extremely affordable to someone else.

The latest evidence: My father’s experience living in Thailand 🇹🇭 then vacationing in Cabo San Lucas 🇲🇽. Unsurprisingly, he was shocked by prices in the tourist destination (read: trap) 🤣

Life abroad is customizable to your budget.

If you want to venture to a new country and save money, you can.
If you want to maintain your quality of life, you can.
If you want to access a more luxurious lifestyle than you do at home, you can.

You can spend far less than you do in your home country. Just don’t expect a 10x improvement in your quality of life. You can also spend just as much as (if not more than) you do at home too.

I spend just as much ($2-4k per month) here in Latin America as I did in the United States 🇺🇸. But my quality of life is much higher.

So again, cost of living depends far more on your lifestyle than the region where you live.

3. Each country & each city are completely different

Generalizing across the region of Latin America is tough. Even writing this essay is difficult.

Why? Because each country and each city in each country is a completely individual experience. If you stay in Rio de Janeiro for a week, did you really visit Brazil 🇧🇷?

For example, Bogotá, Medellín and Cartagena in Colombia are night-and-day different in every aspect.

  • Bogotá — Year-round alpine fall climate. Sophisticated, worldly, business culture. Capital. Bustling megacity. Cold personalities.
  • Medellín — Year-round moderate spring climate. Fast-paced but comforting entrepreneurial culture. Large small town. Overly friendly personalities.
  • Cartagena — Year-round beachy summer climate. Relaxed, nonchalant but scammy business culture. Most affordable large city in Colombia.
Differences between Colombian cities

This is just a microcosm inside one country in Latin America. If three major cities in one country differ this much, you can imagine how much they compare with cities in other countries in the region.

Your experience in neighboring Ecuador 🇪🇨 will be unique to that of Colombia or Peru 🇵🇪. So try to treat each city and each country differently. Just because you hated Costa Rica 🇨🇷 doesn’t mean Panama 🇵🇦 won’t be the perfect homebase.

4. Most expats in Latin America are running from something

I’ve noticed a stark difference between the expats I’ve met all around the world. And this is not a positive realization.

Most of those I’ve met in Latin America aren’t the most successful, most driven, most productive bunch. In fact, most of the expats I meet here are running from something in their home country – whether it’s drugs, bad relationships, money issues, or unresolved psychiatric problems.

I’ve met some incredible, interesting people. I feel like I’m a magnet for them. And that’s a great trait I’m learning to lean into.

But with more connections come more deadbeats.

5. LatAm chaos is both good & bad

Latin American life is generally very disorganized and chaotic. But where there’s chaos, there’s opportunity.

Across the region, bureaucracy is rampant. Tax enforcement capacity is low, regulations are lacks, and “rules” exist but aren’t strictly followed. This applies not only to locals but to expats as well.

What you may read in a country’s legislation is often different than what is practiced in reality.

One example – I don’t condone tax fraud or tax evasion in the slightest. You can legally reduce your taxes quite easily (especially if you’re not from the United States). But as the tweet below shows, most of the Latinos I know do not pay taxes.

Central and South American personal income tax rates are not friendly to local earners (if you have foreign income, they are friendly). Yet, very few people actually pay the rates they’re supposed to pay.

How?

First, most transactions are cash and off the books. Second, they have ways to reduce their taxable income to show they’ve earned less than they actually did.

Plus, about half of the expats I meet in Latin America do not pay taxes in their new country either. In some cases, they don’t even exist in that jurisdiction’s tax revenue system.

Another example – If you have access to influential, well-connected people in Latin America, life is a lot easier. They can get things done far more efficiently than if you try to get things done yourself.

I know a few people with connections in the military, large corporations, and politics and they’ve been able to do me favors that I would’ve never had access to without their help.

So where there’s chaos, there are advantages 😉

Latin America is what you make of it. For some, this life is overwhelming. They enjoy the rules, rigidity and structure of Western life.

And that’s fine.

For me, I enjoy the ability to customize the experience for my tastes. That kind of freedom and control is exactly what I want in this phase of my life.

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What should I cover next?

I have a question for you:

If I were to dedicate the next Freedom Files YouTube video to you and one challenge you’re facing right now, what would that issue be?

Typically, I get something like the following:

  • I can’t find a remote job
  • I don’t know the right long-term location for me
  • I don’t know how to start a business
  • I am a digital nomad but haven’t settled in a country
  • I pay way too much in taxes and need a solution
  • I want to invest in countries before they are popular

Let me know by emailing or DMing me. I’ll write about it publicly because many others likely have the same challenge as you do.

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