Living Abroad: The 12 Dark Truths Of Working Remotely

SUBJECT: What You Don’t Think About When You’re Dreaming Of Moving Abroad

Living abroad has been an adventure, to say the least. In February of 2020, I sold everything I owned and moved abroad to Romania. I’ve since lived in Qatar, Brazil, Hungary, Costa Rica, and now Colombia.

Working remotely, while living abroad, was something I envisioned for years. I would dream about it as I laid in bed at night.

It was an obsession of mine. There was nothing and no one that was going to stop me from seeing the world. From making own money. I had a big world to see, an empire to build, and I was going to do these come hell or high water.

I hated being confined to an office. I didn’t want a job or a stable paycheck. I didn’t want to report to a boss. I had to be free, I had to work on my own terms. 

I made this dream a reality finally, and I’m only getting started. Though I haven’t been at this life for very long yet, I already can say I wouldn’t trade the experiences I’ve had for anything.

I’d do it all again in a heartbeat. Moving and living abroad has changed my life for the better, in many ways. This is a lifestyle our grandfathers wouldn’t have dared to dream of. The internet didn’t even exist in their day.

Back then it was only the mega-wealthy and rich that got to travel the world.

This is why film franchises like James Bond (007) were so popular in those days. It was because those films gave people the opportunity to see other parts of the world. Seeing the world on a screen was the closest people would ever get to the life I now enjoy.

The world is a different place now

Of course, not all the changes have been good, but this one has been.

Not everything about living abroad is a walk in the park, however, especially when you’re new to the lifestyle.

There were dark truths I had to learn about living abroad, and I wasn’t aware they existed.

In this article, I will detail what these were. The list made it to 30, but I’ve narrowed them down to a list of 12. I saw none of these coming, so it’s my hope this article will help that not be the case for you.

Other expats I’ve met have told me they had a similar experience. 

Some of you might be wondering what I’m talking about. It’s important to note if you decide to embark on this life abroad, that not all of you may experience each one of these.

I’ll bet you’re likely to run into at least some of them.

So let’s get right into them…

1) You find out real fast if you’re self-motivated or not

Once you leave your 9-5, time moves differently, and not always in a good way.

Growing up, I would hear stories from older men about how when they retired, they felt like they had less time to do the things they wanted to do.

At the time, I never understood how this could be.

Now, this is the most counterintuitive point of this whole article, and might also be hard for a lot of you to understand too (until you’ve experienced it).

While I’m by no means at all retired, it certainly feels that way for the first few months after leaving your 9-5 and living abroad.

Yes, this is even when you’re doing your freelance work. Or whatever else you’re doing to make money online.

Leaving your 9-5 to go work on the internet all day, in another country, feels like the ultimate freedom, and in a way it is.

Time starts to move differently than what you grew accustomed to all your life. Even when you’re a kid, you spend your whole youth in school for most hours of the workweek.

Then you graduate, you get your 9-5 job and it’s the same time structure: work during the week and have weekends off to do whatever you want.

When you’re self-employed, you don’t technically “have” to be working between the hours of 8-5, five days a week. You become your boss, and everything is up to you now. Everything becomes your fault, your responsibility. Your results are your own, and you no longer have anyone to answer to but yourself.

As you take on more clients, of course, this starts to change a little. Even then, however, it’s nothing like the structure you became accustomed to growing up.

What I’m getting at, is this is all a bit of a mindfuck at first. When you set down in your 1st country, you’re on Cloud Nine.

Everything is new, everything is fresh, everything is exciting.

In your first 4-5 days you have this incredible feeling inside. The feeling of freedom, prosperity, and abundance.

However, at some point, it comes time to sober up. You can’t just sit around, drink, smoke cigars, and explore all day.

At some point, you have to be able to sit down and start working. You have to have the self-discipline to force yourself to work.

A lot of guys move overseas, and they realize they don’t have this self-discipline, even if they thought they did.

Often guys will move to places where the weather is perfect, the girls are everywhere and the beers are flowing. Four days of partying turns into a week, a week turns into two weeks, which turns into a month (or even longer).

They blow through their savings, even in a cheap country, within a matter of months and have to end up going home with their tail between their legs. 

I’ve seen it happen to more than a few guys.

The takeaway here:

Make absolutely certain you’re the type of guy that can command himself to sit down and get work done, with no one but yourself telling you to.

You may think this sounds ridiculous, but believe it happens more often than you’d think.

2) The ”Illusion” Of More Time

There are other parts to this too. With more ”free” time, an illusion is created where you feel like you have all this time to get personal projects done.

While this is true to an extent, this illusion of more time makes you think you have more hours than you actually do. There are still only 24 hours in each day. A lot of guys start trying to take on more personal projects and goals while attempting to build their online businesses at the same time.

Reading more books is one example of this, attempting multiple businesses is another.

The reality is:

You have no more extra time than you used to have. What’s more, is now YOU are solely responsible for how you use every minute of your day.

You’re on no one else’s clock but your own.

Tim Ferris has a great section in his book ”The 4 Hour Workweek” where he talks about this (Chapter 15: Filling The Void).

What ends up happening is many guys get depressed when they realize it’s just as hard to get personal projects done as it used to be, if not harder.

Again, this is similar to what men who retire end up realizing.

When you retire, it’s not like there are suddenly 36 hours a day now to work with. No, just like your whole life, it’s still the same 24 hours a day everyone else has.

You also still need to sleep, you still need to eat, you still need to work and build your business.

So the main takeaway is that this is all a big mental adjustment you have to get used to. You are now 100% completely responsible for every hour of your day.

3) Time Zone Difference

This one can be annoying, and for more than one reason.

The first reason is communication with your family and friends. You can’t just pick up the phone and call people back home during the day. When I was living in Qatar, I couldn’t just call at 10 am in the morning. That would be 3 am back home. This meant I had to plan my conversations with people around the time zone difference, which at times was inconvenient.

This was the first of many things I noticed people take for granted back in the U.S. This factored into my decision a little when I decided to move back over to a similar time zone (leaving Qatar to come to Central/South America).

The 2nd reason this is important is because of client work. When you’re a freelancer, many of your clients will be located in different time zones.

This might mean at times you have to wake up at 5:00 am to be on a client Zoom call. Or you may have to stay up until 1:00 or 2:00 am to make one.

Just something to be aware of when choosing a place to live. Also when choosing what type of freelancing work you want to do. Following the Freelancer Profit Manual, you will have better control over this.

4) Dealing & Navigating Around Temporary Residence VISA’s

When I lived in Qatar, this situation was a bit annoying to deal with. I wanted to get back into Europe and bring my girl with me. However, with the “world situation” going on, this was impossible.

Even knowing people in charge of immigration didn’t help. I lost many days dealing with the headaches this process entailed.

Luckily I hired someone to handle certain aspects which made the process much easier to get around.

There is really nothing I can say that will truly prepare you for the hell dealing with VISA’s can potentially present you with, but hopefully at least just reading this section will help you somehow.

Unless you are planning on staying somewhere for an extended period of time, save yourself the trouble of dealing with this.

Now, of course, many of you reading this will fall in that category (staying in 1 place long term) 

For all of you:

My recommendation would be to hire someone as I did. Someone that knows all the local in’s and out’s of VISA’s and residencies.

It gets easier the 2nd time I imagine, and even easier the 3rd. Like anything in life, living abroad comes with some growing pains.

5) Social Isolation

Before you get the wrong idea, hear me out on this one. Human beings are social animals, we need a certain sense of community in our lives. When you first leave the rat race, even if you couldn’t stand being around people all the time, there can still an intense feeling of isolation you eventually feel.

Most of you may have even recently experienced this with the recent lockdowns to some degree. When you move abroad, it’s a similar feeling.

All of a sudden people you used to see every day, people you used to socialize with daily, all this goes away (at first).

Of course, if you stay in one location you’re more likely to cultivate local friendships and acquaintances, but even then it takes a few weeks-months, especially if you’re more of an introverted type.

Being the introvert I am, this is not one I expected to experience. In fact, this was probably the last thing on this list that I thought about.

To my surprise, it turns out even an introvert like me needs a certain level of weekly social interaction with people.

Lockdowns definitely compounded this for me, though I know ex-pats were experiencing this long before lockdowns.

It IS a temporary problem, just make sure you’re aware this is likely to creep up sooner or later, and when it does, it’s better you see it coming first, which I why I’m including this point.

Also, understand that life expatriating will be lonelier if you’re constantly moving from one country to another. Longer stints in one location will help you get around this.

6) Living Abroad: You Will Miss Your Family & Friends

After a couple of months give or take, you will start to miss your family and friends. You will see them post things on social media, and it will hit home that you’re here and they’re back there.

This will happen more than once too.

You will see your friends post the great time they’re having at a happy hour back home. At a place, you used to go to. You will have to witness scenes like this over and over again, for months. Eventually, the FOMO feeling wears off, but at first, this can really mess with your head (and emotions).

Just know this is likely to happen. Even if you got rid of social media (which most expats don’t want to do because they run their businesses there), it’s likely at some point you’ll get the nagging feeling about missing home.

When you do, they’ll all be hanging out together without you, back home.

Knowing something like this is coming down the pipe, will better equip you to deal with it once it gets here.

The solution:

Meet up with locals and begin building a network there. Also, connect with like minds to speak to.

You can join my private chatroom here.

7) You May Start To Question Your Decision

Self-doubt is likely to hit you at some point. While I never felt I made a bad decision about traveling abroad, I’ve spoken to some who did.

You will wonder if you made a mistake, going against the social grain and paving your own way.

You’ll fear you ostracised yourself too much from society. You might ask yourself questions like:

”Did I leave my country because it’s truly that bad? Or just because I’m a social outcast that can’t get along with people?”

”Did I really become a freelancer or entrepreneur because I wanted to? Or was it just because I couldn’t hack it in the corporate world?”

”Am I just faking my success? Will this only last a few months and then I’ll have to go crawling back with my tail between my legs?”

”Am I doing this to improve my life? Or am I really just lazy?”

These are normal feelings to experience. It’s best to just observe these feelings when they come up.

Observing the feelings Vs. acting on them are two different things.

8) Safety Concerns

Of course, this will vary by country. This is also one you can avoid if you choose your country with this in mind beforehand. There are plenty of 2nd world countries where safety is not an issue at all.

In 3rd world countries, they become harder to avoid.

I can tell you in Colombia, this was something I had to be very careful of. You have to think about where you’re going. Unless it’s in a nice area, you have to blend in instead of wearing your nice watches etc.

Also, social unrest is at an all-time high in the world. People are struggling financially and going stir crazy. I witnessed a month-long protest outside of my window. Full on shooting and tear gas.

However, of every point on this list, this is the one point you can avoid with a little forethought (if it’s important to you).

Even in the US, not every city is safe. When they are, people usually take that for granted too.

9) Language Barrier

This one should be obvious, but even if you live in a country where they speak decent English, most of the time you’ll still have to overcome the language barrier for simple things.

While this may not sound like a big deal, it gets old when you have to do it over and over. To top it off, you’ll also get stared at quite a bit. People will outright stare at you, most of the time not even realizing they’re doing it. I can’t tell you how many times I’ve caught people staring at me for being a foreigner, and I’d catch them and they quickly look away.

I’m to the point now where I can feel someone looking at me before I even see them. I’ve basically developed a 6th sense over it.

If someone had told me these things 2 years ago, I would have thought to myself: ”Who cares!”.

I still don’t care truthfully, but it’s still different when you’re dealing with this on a daily basis, which doesn’t happen back home.

It can get tiring, but as with everything on this list. If you simply plan ahead you can mitigate 90% of the annoyances.

Eventually, you start to become a little desensitized to it, but if it annoys you too much just pick a different country.

10) Shipping Challenges

This is vary depending on which country you go to, but some countries are much more difficult than others are when it comes to receiving packages.

I have a friend who ordered expensive items only to have them sent back to the carrier. Several of his items were held at customs and they had asked him to pay an exorbitant fee for the ”privilege” of having his item delivered.

He had to get refunded on some of them, and/or had to wait months after he placed the order to receive it.

If you’re in e-commerce, make damn sure you know what the country’s shipping and receiving policies are.

Otherwise, in most countries, you will get anything you want with ease. The only time I had an issue personally was in Qatar.

11) Everyday Life Is Less Convenient In 2nd Or 3rd World Countries

While the cost of living may be lower, you pay for this in other ways (usually unanticipated ones).

People in the United States take for granted the level of convenience they enjoy.

This is one of the first things I noticed once I got settled abroad. In America, you can hop in your car and everything you could ever want is within a 15-minute drive. Even if isn’t, just order it from Amazon and you’ll have it within 1-2 days.

Grocery stores, convenience stores, and drug stores are all still very accessible in most countries.

Outside of these three, however, everything else can be hit or miss depending on the country.

When it comes to businesses, malls, restaurants, etc., all bets are off. This is unless you’ve thoroughly done your research.

Sometimes, you will have to go to 2 or 3 different stores to get everything you’re looking for.

These are all things people in America take for granted, as far as how easily accessible, they are. Everyday conveniences, everyday items, etc.

First-world countries like the U.S. or Japan may be very expensive, but at least things are convenient.

Just understand there are trade-offs to everything, and living abroad is no different.

12) Managing The Separation Of Work & Home Life

When you’re traveling abroad running your business, the line between work and home life is blurred. The best way I can explain it is you don’t view it as work or sitting down with your girl.

Everything is one and the same.

This is your life now and trying to maintain a balance will simply make you go crazy as there’s no balance.

When you work from home, or a cafe, basically anywhere other than a formal office, it becomes harder to separate work time from personal time. This problem is still present abroad too. You must teach yourself to be intentional about when your work hours are, and when your play hours are.

You must teach yourself to be intentional about where your workspaces are (even within your apartment) and where your lounge space is.

The point is:

This is your life now and you will make time for everything. You can’t just work 24/7 and expect to be happy. Instead, make time for taking your girl out for a nice date, going out with friends, and still crush it with your goals.


I hope you found this article helpful. If you have any questions or concerns about living abroad, I want to hear your comments below. 

Some other great articles on this topic are:

What’s your perfect day look like

11 Tips for Traveling Internationally

Escape the 9-5

Until next time.

Always the best,

Dylan Madden

About Dylan Madden

My name is Dylan Madden. I've written over 300+ articles for those who want more out of life and are interested in traveling the world. I am from US city where most people work the same old job for their entire life. Now after traveling to 18 countries. I've set up a home in Dubai where I spend my days helping freelancers build successful businesses within The Real World and on the blog Calm and Collected. Within this website you will find the motivation and action steps to make your life better.

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