7 Years Abroad Taught Me What Freedom Actually Costs

What we’re talking about today: What does it actually cost to live abroad? After 7 years and 27 countries: the money, the relationships, the identity, and the 4 requirements before you go.

Good morning from Tbilisi.

The view this morning looks like freedom. Mountains. City around me I chose. Coffee in hand.

You know that photo. You’ve scrolled past a hundred versions of it, and every time, some part of your brain goes: “I could live there.”

Could you? Simple question. Most people never actually answer it, because they’ve never seen the price tag.

After 7 years abroad and 27 countries, I can tell you freedom costs way more than a plane ticket and a nice view.

It costs money. It costs certainty. It costs comfort. It costs relationships.

Sometimes it costs the person you, your family, and society expected you to be.

That’s not a warning to stay home. It’s a receipt. And in 2026, with half your feed selling you the laptop on a beach fantasy (btw working in the sun is terrible), somebody should hand you the actual bill before you blow up your life chasing a filtered version of mine.

Here’s the full price.

6 costs, then the four requirements before you go.

I. Freedom Costs Money

You don’t need to be rich. You need income that moves with you.

Remote job, online business, newsletter, digital products, a service business. The model doesn’t matter. What matters is one question: does it keep paying when your location changes?

Now here’s where almost everyone aims wrong.

They ask: “What’s the cheapest country?”

Wrong question. The goal isn’t the cheapest country. The goal is a country where your income provides the exact lifestyle you want.

Look at location as an income multiplier.

Same $10K a month. In New York City, most of it walks out the door for rent and survival. In Tbilisi or Warsaw, that same $10K multiplies. More money for your business. Your investments. Your future. Your actual life.

You don’t get a raise. You get a better exchange rate on your entire existence.

That’s the whole game. Everything else is decoration.

II. Freedom Costs Certainty

Everybody is addicted to certainty.

That’s why people live in the same town their whole life. Never start the business. Never pull the trigger. “It’s not the right time.” I know someone personally who’s been saying that exact sentence for a decade.

Every week I break down how to build portable income, pick your country, and design a life you don’t need a vacation from. 7 years abroad, boots on the ground. Subscribe and build yours.

10 years. Same town. Same faces etc.

Meanwhile me and a core group of people completely changed our realities, and the realities of the people we love, in the same window. (Same decade. Same 24 hours in a day. Different decisions.)

And look, I’ll be honest: I love certainty. It’s part of why I built the life I built.

But here’s the thing nobody wants to hear.

You cannot research your way into knowing if a country is for you.

People send me question after question. They watch every vlog. Read every article. Months of “research.”

Does it work? No. You’ll never have an accurate view of a country until your own two boots are on the ground.

So run a test instead: 30 to 90 days. Go grocery shopping. Work normal hours. Use their transportation. Feel what a random Wednesday is like after the excitement wears off.

Research reduces risk. Experience produces clarity. That’s the trade.

III. Freedom Costs Comfort

Familiar places. Familiar faces. Familiar routines. Maybe even your language.

Gone.

I’ve been in countries where I didn’t know a single person and couldn’t speak a word of the local language. That’s a level of discomfort most people are not ready for.

Here’s the reality: you’re never going to be ready. You’ll adapt, improvise, and overcome once you’re actually there. Not before. OOHRAHHH.

(And for the worriers: it’s 2026. Bolt handles the taxi, Google Translate handles the menu. I had none of that when I started. I was winging it daily. You have it easy and I’m only slightly bitter.)

But don’t miss the actual point. This isn’t about chasing discomfort for its own sake.

It’s about putting yourself in situations where you have to become more capable.

When I lived in America, my business made about $1,200 a month. I had my comfort, my routines, my little stories about who I was and why things were the way they were.

Living abroad deleted those stories.

Nobody around me knew “the old Dylan.” To them I was just an American in their country. The only thing I could be judged on was what I did next.

So I did. That shift, from living on my history to living on my actions, is a huge reason the guy making $1,200 a month eventually built his first million.

Changing countries won’t magically make you successful. But comfort lets you avoid developing abilities. Discomfort sends the invoice.

I write about one thing: turning your laptop income into a life you actually chose. Country breakdowns, real numbers, zero fantasy. Subscribe below

IV. Freedom Costs Relationships (Then Upgrades Them)

This is the one that keeps most people home.

Not money. Relationships. “What about my friends? What about my family?”

Let me give it to you straight.

If a relationship dies because you decided to take control of your own destiny, it wasn’t a true relationship.

Did I lose friendships over 7 years abroad? Of course. We fell out of contact. I went on my path, they went on theirs.

But that was going to happen anyway. Stay in your hometown forever and watch: at some point they go their way regardless. Knowing someone since childhood doesn’t make them a friend. Most friendships are friendships of circumstance, held together by convenience and nothing else.

What you’ll actually find abroad is fewer, better friends.

And here’s my confession on this one, because I earned it the hard way.

In the early days of my business there was a four-to-five-year stretch where I barely saw or talked to my family. All business. All focus. That’s on me.

Moving abroad fixed it. When you’re on the other side of the planet and the only people from home are family, you talk more. You get more real. More authentic. My relationship with my family is better now than it ever was when I lived twenty minutes away.

But there’s a second half to this cost, and the live-abroad influencers won’t say it:

At some point, you need community. A life where you can go anywhere but belong nowhere stops feeling like freedom.

The nomads bouncing country to country, year after year, no roots? Somewhere in their mid-30s the bill arrives: no wife, no kids, no community, a phone full of places and nobody to call. I watched a 5-month stretch of nonstop movement through Europe and North Africa tank my own productivity and my mood. Best hotels, good flights, hated it.

Explore. Then plant. One or two home bases, real routines, real people. Travel becomes the side quest instead of the whole identity.

It took me about 7 years to find where I fit. Worth every wrong stop.

Which of these costs is the one holding you back? Tell me in the comments. I read them.

V. Freedom Costs Your Old Identity

The people around you will not understand. Plan on it.

When I left, people close to me had my future fully written: “You’ll be back at 27. No job experience. In debt. Working an entry-level job until you’re 30-something.”

That was the actual forecast. From people who loved me.

To this day, certain family members still ask: “So Dylan, when are you coming home to get a job? You’re American. Why would you want to live in Georgia?”

I don’t explain myself anymore. Why not? Because they’re judging my life through their era, their experiences, their map of reality. Where I’m from, the best job you can get is working on the railroad. No disrespect to anyone on the railroad. But I wasn’t built for it, and I knew it.

Here’s the filter for whose opinion counts:

Would you take fitness advice from a 350-pound guy mid-feast at McDonald’s?

No? Then why let someone who’s never left their hometown rule on whether you should live abroad? Why let someone who’s never built anything rule on whether your business can work?

They’re not bad people. They just haven’t made the jump. So at some point you have to be the bird: jump off the branch and find out if you fly.

Worst case? You come back and regroup at the drawing board. That’s the entire downside. People treat it like death. It’s a return flight.

You will disappoint people who already planned your future for you. That’s one of the prices of choosing it yourself. Pay it.

Weekly breakdowns on portable income and living abroad, from someone actually doing it. Subscribe, use what works.

VI. Real Freedom Eventually Means Choosing

When you first get free, you want zero commitments and unlimited options. Go anywhere, do anything, whenever, with whoever.

Experience that stage. Genuinely. Especially if you’ve spent your whole life confined to one town, one job, one script.

But here’s what nobody tells you: unlimited options eventually become their own trap.

If you’re always ready to leave, you never build anything that requires you to stay.

True freedom was never the packed backpack. True freedom is the power to choose your commitments. Where you live. What you do with your time. Who you build a family with. What deserves your loyalty.

The point of 27 countries was never to stay homeless forever. It was to see enough of the world to recognize the life worth choosing, and then choose it.

Real freedom is being able to say: this is my home. These are my people. This is what I’m building.

That’s it. That’s the destination the backpack was supposed to lead to.

VII. The Four Requirements Before You Go

Wrapping this up the practical way. Four things I’d want in place:

1. A clear reason. Know what you’re moving toward, not just escaping. Mine: a city close to mountains and nature, no job dictating my hours. I hated the 8-hour shift I could finish in 3. If you can’t define the life you want, you can’t evaluate whether a country provides it.

2. Portable income. Reliable, location-independent, with levers you can pull to increase it. Remote work, business, newsletter, products, services. Doesn’t matter which.

3. Financial breathing room. 6 to 12 months of living expenses saved, plus the income flowing. I’ve never once seen someone combine those two and have a bad time abroad. I did the opposite: a couple hundred bucks in the bank, $1,200 a month coming in. It worked, but it made everything fragile. Don’t copy that part.

4. A destination worth testing. Safety, prices, infrastructure, banking, business setup, quality of life. Then boots on the ground for 30-90 days.

Notice what’s not on the list: having your whole life figured out. You need income with a margin, a buffer, and enough courage to run the test properly.

VIII. Calculate Before You Escape

Here’s where the two camps split.

Camp one reads this, nods, saves it, and keeps living a life they never consciously chose. Camp two puts numbers on it this week.

Because before you randomly pick a country, you need to calculate the life you actually want. In writing. Actual tangible numbers. The space, the lifestyle, the family picture, the money left over after expenses for investing and building. Then the income it takes to get there.

Most people have never done this once. They know their salary. They’ve never priced their dream. So it stays a dream. Fantasies don’t have price tags. Goals do.

That’s exactly why I built the Freedom Calculator.

Put in your numbers. It shows you what your ideal life costs, where your income supports it, and the gap you’d need to close. It takes 33 seconds, and it turns “someday” into a number you can attack.

I called it the Freedom Calculator because freedom has a price. You’d agree with that by now.

But staying in a life you never consciously chose has a much bigger one.

Run your numbers here + get a full country breakdown without needing to give your email.

Always the best,

Dylan Madden

P.S. If this reframed freedom for you, share it with the friend who’s been saying “it’s not the right time” for a decade. You know exactly who.