Some Digital Nomad Challenges: Not as Glamorous as Instagram

The life of a digital nomad is the best way to balance work and life. Over the past six years, I’ve had all the ups and downs that come with working from home while traveling the world.

I get to live in places where a dollar goes further, so I can work part-time and save money at the same time. I have a lot of time to sleep, work out, and eat well. I can also hike up a volcano or scuba dive in a cenote on the weekends if I want to.

I wouldn’t change anything about my life, but it’s not as perfect as it looks on Instagram. There are pros and cons to everything. So, if you want to live like a digital nomad, here’s what you can expect.

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Digital Nomad Challenges

To become a digital nomad, here are six challenges you’ll have to overcome.

Hard on Relationships

Relationships are hard to keep going when you live this way, whether with family, friends or on a date. This is the most challenging choice for me.

I’ve seen my family once or twice a year in the last eight years. I miss them a lot, and even though video chats help, it’s not the same as being with them, doing something together, or hugging them.

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I also have a lot of young nephews, all of whom are growing up without me. I feel bad that I don’t spend more time with them, but some of them have said they’d like to come with me on my trips. If I can motivate them, I hope that will compensate for all my wasted time.

Digital nomads are more open and easy to get along with when making friends. But either they or I have to go somewhere else at some point. Many of these friends and I have met up in different parts of the world, but you never know when or if you’ll see them again.

Regarding dating, it can be hard to build a strong relationship if you move around the world quickly. Most digital nomads I know are single, from what I’ve seen. If you get into a relationship, you may have to be apart for a while, especially if you live in different countries. It could even affect where you can go together since some passports are better than others.

It’s Difficult To Get Your Head Around A New Culture

We tend to think that stress only happens when bad things happen, but we can also feel stressed when good things happen.

This is clear when you think about travel. It can make you feel more hopeful, empathetic, and creative. It can also bring you closer to the people you are traveling with. But it can be hard to find a place to live, figure out how to use public transportation, communicate with people who don’t speak your language, deal with unexpected events, and keep your daily routine, especially if you are traveling alone and don’t have your usual support system.

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This is one reason why I like to travel slowly. I usually want to live in one place for a year or two because it helps me get into a routine, make many friends, and get to know my city. After a month or two, it doesn’t seem so hard.

Riskier Housing (and Expensive)

It can be hard to find and expensive to rent short-term housing, especially if the place is popular. In May 2022, I wanted to spend the summer in Lisbon, but it seemed like everyone else had the same idea. I started looking for a place a month before, but that wasn’t enough time. Airbnbs were either $3,000 per week for a luxury one-bedroom in the city center or $500 per week for a one-bedroom far from the city center with bad reviews.

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Spotahome, which is usually aimed at students but was the only option with a reasonable price, is where I ended up booking. The landlord I was talking to was hard to get in touch with, so I looked her up and found over 50 bad reviews that said she was dishonest and rude. After writing a blog post about the situation and having the Portugal Country Manager read it, I could get my money back.

So be careful who you book with, and if you’re staying for more than a week, always check out the place first.

Usually, the first thing I do when I get to a new place is book a 10-day stay through Airbnb. Once I’m there, I look at apartments in person. I usually find these places through Facebook or WhatsApp groups for digital nomads and ex-pats.

But if you don’t sign a lease for at least six months, you’ll pay more than people who live there. This is because there might be an extra tax (like with Airbnb), landlords have to furnish the apartments, or the place is only popular at certain times of the year. Hence, they only make money at those times.

In some countries, like Argentina, landlords need a “guarantee,” which means that two people have to say they trust the renter. If the renter doesn’t pay, these people will have to pay for it. Foreigners have a hard time getting a guarantee for obvious reasons, and since landlords are breaking the law, they have to charge more.

Complex Visas and Immigration

I’ve lived and worked in about seven countries, so I know much about visas and immigration. I’ve found that most countries have tourist visas that last between 3 and 6 months and can be gotten when you arrive. I often leave the country for a few days, and when I return, it’s easy to get a new visa.

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But I’ve also seen that immigration starts to take notice and get angry if you keep doing this for years. Legally, you must pay taxes in a country if you live there for a certain amount of time, which varies from country to country. This is true even if you don’t work there.

I remember getting a text message from a friend who had lived in Argentina for a long time. Like many ex-pats living in Buenos Aires, he took the ferry to Colonia, Uruguay, in the morning to renew his visa. He stayed there for a few hours and then took the ferry back to Buenos Aires in the evening.

The immigration officer he got didn’t like it and threatened to take away his passport, which would have been the same as sending him home. Everything worked out in the end, but my friend was scared.

Getting visas for digital nomads could be the answer to this problem. Even though there have been a lot of talks about them, many countries have not yet made them official.

I’ve learned from my research that many of them are also hard to apply for. For example, it’s common to need a criminal background check, which you would have to do from your home country. Others will require a substantial income, that you pay taxes or health insurance.

Work May Be Less Predictable

Even though the number of remote jobs has grown by 87%, I still see a lot of employers who aren’t sure about letting their employees work abroad. Because of this, most digital nomads have odd jobs. They usually have contracted workers, freelancers, consultants, coaches, or people who work for themselves in other ways.

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It also means that we have less control over our income. We don’t always expect to get the same amount of money every week. So, when a recession happens, we’re usually the first to lose jobs, clients, or other ways of making money.

Not Everything You Find on the Internet Is Reliable

The reliable Internet is probably the worst thing to happen to a digital nomad. If you’re from the West and haven’t traveled much, this might make you scratch your head.

The Internet is reliable in more developed countries, big cities, or countries. But in poorer countries, there aren’t as many Internet cables. In the Philippines, for example, the Internet is excellent in Manila but terrible on Boracay, the most popular beach destination and where most travelers would rather be.

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Then there are times like when a hurricane comes through. When I lived in Playa del Carmen, Mexico, that’s what happened to me. About half of the digital nomads were lying to their employers about where they were based. Hence, it was pretty funny to see them all freak out when the power went out during the storm. Many people went to Merida, Mahahuel, or even Mexico City to find work during those few days.


The digital nomad lifestyle isn’t a magic pill that will solve all your problems. Still, it can help you live a more balanced, healthy, and exciting life.

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