Digital Nomads: The Dark Side

The Big Picture 5/8: What you’ll be up against and what you should think about.

Marc Knaup
Oct 31 · 15 min read

Judging from the overwhelmingly positive content on social media, living like a Digital Nomad is a piece of cake. Just take your laptop, travel to the places you’d love to see and earn your income remotely from there.

But — like so often in life — that’s just the tip of the iceberg.

The Big Picture

You’ll have to organize a lot

  • Finding good locations, accommodation and transport will be a hit or miss sometimes.
  • You’ll have to find and book an affordable accommodation and transport repeatedly, in places you don’t know much about.
  • You’ll have to do plenty of research, and use a lot of different services.
  • In many cases, you’ll fly. That involves check-ins, security checks, flight delays, baggage allowance, and baggage claims.
  • You’ll have to match dates for accommodation and transport with visa requirements, family events, business events, and other constraints.

Tip: You’ll have to plan less often if you travel slowly.

Your expenses can go up

  • Short and medium-term accommodation is more expensive than long-term.
  • Services like Airbnb and booking.com are more expensive than local bookings.
  • Transportation between cities and countries will become a new recurring expense.
  • Booking accommodation and transport on short notice is more expensive.
  • You may have to pay for your visas.
  • You may become tax-resident in a high-tax country.

Tip: Travel slowly. The further you can plan ahead the cheaper it gets.

Tip: Book accommodation locally if possible.

Tip: Websites like Kiwi.com, Skyscanner, and KAYAK are great for finding cheap flights. Kiwi.com has the most flexible search but note that there are many negative reviews of people who have used the service to make their bookings.

You’ll also live in cities that you don’t like (at first)

To find cities you love, you’ll have to weed out the cities you don’t. You won’t know in advance how much you’ll like a city, and the picture that you have in your mind may be proven wrong once you get there.

Brace yourself for a lot of surprises.

Tip: When moving to a new city, only book short-term accommodation. Spend some time finding a neighborhood where you’d like to stay for longer.

You’ll have to consider your family situation

While you’ll be traveling around the world, your family will likely stay behind. Thanks to video calls and social networks, you can easily stay in touch, but you’ll still feel disconnected from everyday family life. You’ll also miss some birthdays and other significant family events.

Occasional trips to your family can make up for some of it, but it’s not going to be the same.

Tip: Your family can also visit you. You’ll know many great places by then and how to get and live there affordably.

Some family events will likely happen without you

It’s also possible, but even more challenging, to live nomadic as a family if your kids and partner are willing to travel. There are several families on the road, and they share their experiences and learnings online.

Unfortunately, the effect it has on the social development of kids is mostly unexplored. It’s likely harder for them to cope with the recurring loss of close social connections than it is for adults.

Tip: Do a lot of research and talk to other nomadic families, and learn from their long-term experience.

You can feel lonely at times

Loneliness is a common issue that affects many remote workers.

The following list will give you an idea of what you’ll be facing:

  • Your family, friends, and colleagues will be far away.
  • You’ll miss out on personal events in the life of people you care for.
  • You’ll have to solve a lot of problems in foreign places on your own.
  • You’ll constantly meet new people and make new friends. But you’ll leave each other behind after a while once one moves to the next location. Therefore, friendships are often shallow or temporary.
  • There are plenty of communities, events, and opportunities to get to know people, but starting is often hard. And in the next location, you’ll have to do it all over again.
  • Finding a significant other will be even harder. You’ll be living in different countries with different cultures and languages. You may find someone who’s interesting, but they may not be willing to travel with you.

Tip: Talk openly about feeling lonely, ideally with someone you trust.

Tip: Travel slowly. The longer you stay in the same location around the same people, the closer you can bond with them.

Tip: Live in a strong community. Some coliving spaces, for example, focus on long-term stays and building a close community. Such communities can extend well beyond each member’s stay.

Remotely Well Done by Very Nomad Problems

You’ll lose routines and good habits

How long it takes to form a new habit varies widely — 66 days on average.

Living in one location for longer makes you more effective in your daily life because you’ll establish good habits and routines. They help you focus on the important things: eating healthy, staying fit, being productive, sleeping well, and enjoying life.

But as a Digital Nomad, you’ll move on at some point, and the knowledge about your previous location won’t help you anymore. Habits triggered by location and routines will likely break.

It’ll take a while before your local knowledge, habits, and routines are fully established again.

Tip: Travel slowly to allow for good routines and habits to reestablish.

Tip: Opt for routines and habits that are independent of your location.

Your health can deteriorate

Finding a good gym, healthy restaurants, and groceries will become a recurring challenge. You’ll have to put in some extra effort to stay healthy.

Working from accommodations, cafés, or other nice places often means sitting on cheap chairs for long hours. That’ll be bad for your back and your posture, and one day you’ll start to feel it.

You can also end up in destinations where life is less healthy in general. Examples are air/water/noise pollution, mosquitos, and bacteria that your body hasn’t encountered before.

Doctor visits pose another challenge. You’ll have to find a good one where there is no language barrier and who accepts your health insurance or cash payment. Long-term treatments, tracking and communicating your medical history aren’t easy if you keep changing your doctor.

Repeatedly moving to the next destination will exhaust you, and together with jet lag, they’ll mess with your sleep. All of that will put stress on your body and mind, and if you’re not careful, you can end up in an unhealthy downward spiral.

Tip: Travel slowly and don’t compromise on health. Good health makes life more fun and work more productive.

Tip: Avoid sitting too much. Stand, walk, and cycle a lot. Prefer comfortable seating that supports your back while working. Mix it with working at a standing desk if possible.

Tip: Educate yourself about sleep and act accordingly.

Your productivity can go down the drain

Changing your environment will put a tax on your productivity at first. Every time you move, you’ll have to find good places to work from, and reestablish a productive routine. A different climate and time zone can further drag you down for quite a while.

Depending on where you work, there can be distractions like noise and unstable Wi-Fi. You may find yourself socializing a lot, which is good, but it won’t get you much work done.

There is also the temptation of exploring the city, and spending time on activities other than work. Your mind will wander, and you may feel that you’re missing out on what your new location has to offer.

Tip: Travel slowly and keep reminding yourself that you’re not on vacation. You’ve got enough time to explore, and if not, then you can still come back another day.

Tip: Always focus on establishing a healthy and productive daily routine first. Afterward, you can spend more time exploring your surroundings.

You’ll have to develop a remote work mindset

If you’re used to a local office environment and having your colleagues nearby, then you’ll likely struggle with remote work at first. You’ll have to learn a bunch of new things, such as:

  • Keeping yourself and others accountable over long distances.
  • Managing your work hours.
  • Communicating effectively across time zones.
  • Maintaining the feeling of being part of a team.
  • Managing, communicating, and coordinating remote teams.
  • Letting go of micromanagement.

Tip: Agree and focus on concrete and specific results, not on the time to invest.

Tip: Prefer asynchronous communication.

You’ll have difficulties communicating remotely

Scheduling a call isn’t easy if the participants are in different time zones, up to twelve hours apart. You’ll have to make compromises here to ensure everyone can participate in the call without sleep deprivation.

Digital voice and video communication depends on a stable Internet connection, which, unfortunately, is still a problem today.

Another major issue is noise. There can be barking dogs, traffic, lots of chatter, buzzing coffee machines, and nearby construction sites. Places that offer separate rooms for making calls are rare and noise cancellation is still a hit or miss.

The lack of separate rooms for calls also means that it’s difficult to have a private conversation.

Tip: The best call is the one you don’t have to make — research alternatives for effective remote communication in teams and with customers.

Every Remote Meeting by Very Nomad Problems

Your laptop and phone will become mission-critical

It’s easy to replace a phone when needed in most cities. Clothes aren’t a problem either, and you’ll hopefully travel with backup credit/debit cards.

But if your laptop gets broken or lost, you can face a serious problem. No laptop means that you can miss deadlines or lose income.

Getting a replacement or repair takes time, money and effort. It gets worse if you are in a remote area like Bali. You may even have to make a short trip to another country to get back on track.

Tip: Think through hypothetical situations where you’ve lost your laptop and phone, and how you’ll recover from that. It helps you to find weak spots like inaccessible accounts due to lost two-factor authentication.

Tip: Save everything in the cloud. Use an app like Authy that, unlike Google Authenticator, allows you to back up your two-factor authentications.

Tip: Prefer app-based two-factor authentication instead of SMS-based. The latter is known to be insecure.


Wow, this article is long!

Let’s take a break with Conni, who talks about common newbie mistakes.


You’ll get tangled in tax laws and reporting

It’s complicated. Where you have to file and pay what taxes depends on many factors. Those include citizenships, residencies, countries you stay in, company setup, “center of life” and the timeframe for each. The more you move, the worse it gets.

Each country has its own tax law. You could violate one of them without knowing or at least end up in a gray area.

In the end, you just hope that you’ve got it all covered.

Tip: It can be a good start just to keep filing taxes where you’ve done before, until you’ve figured out something better. Still, do some research upfront.

Tip: Take advice from the web, other Digital Nomads, and this article with caution. Better ask proper tax advisors or local authorities.

You’ll struggle receiving mail

Many companies and government agencies still insist on communication by mail. Sending mail from a country that you’re unfamiliar with can be a little inconvenient. Receiving mail around the world poses quite a challenge.

Your accommodation may not allow you to receive mail. Mail delivery in your area could be unreliable, or your mail may arrive late after you’ve already left.

Tip: Ask your family, accommodation host, coworking space as well as local friends if you can receive your mail there.

Tip: You can rent a digital mailbox, like CAYA in Germany. Your incoming mail will be scanned and made accessible online.

Tip: Check upfront on how customs laws affect local mail and package delivery.

You’ll have to dive into healthcare and insurance

For many, sorting out insurance is more daunting than tax. Most products that you’re relying on today are not suitable for a life scattered all over the planet. Some even become void once you deregister from your home country.

Proper healthcare is most important here. You should take time to research international primary medical insurances, and how it is different from travel medical insurance. You should think long-term, especially when it comes to common chronic conditions like diabetes and cancer. There’s no one-size-fits-all solution.

Health insurance isn’t the only safety net you’ll lose. You may also lose access to job safety/unemployment insurance, nursing care insurance, pension, and other benefits.

Tip: Be very careful with advice. Don’t skip educating yourself and look beyond the price. If someone recommends a product on the web, keep in mind that they may only do so because they get money for that.

Tip: Thoroughly check what is covered. Sports activities are often excluded, as are preconditions, and common chronic conditions like diabetes and cancer. Check that the insurer can’t kick you out upon policy renewal if your health worsens.

You’ll have to register in other countries

  • You’ll have to learn in advance about visa regulations, which keep on changing.
  • You may have to get a visa before entering each country, and extend it while you live there. Both costs time and money.
  • You may have to make a visa run where you leave the country and come back almost immediately to get a fresh new visa.
  • Using the tourist visa while working remote is often a legal gray area.
  • Even if you don’t need a visa, you may have to register and deregister in a country, e.g. when relocating within in the EU as an EU citizen.

Tip: Inform yourself early enough. Visa applications can take a while, and visa options can be very different.

Tip: In some countries, there are so-called visa agencies that take over a lot of the hassle of extending your visa.

You’ll have difficulties to communicate locally

You’ll be going to communicate a lot in English.

Unfortunately, English is not always helpful. Many locals in foreign countries either don’t speak English or at a very basic level. You’ll find yourself communicating with hands and feet, translating back and forth with an app, or just giving it up altogether.

Local signs, shops, and groceries may also be written in a foreign language, which can make everyday life more difficult at first.

Tip: Learn the local language. Just some everyday words and sentences using apps like Duolingo or Memrise can help tremendously.

Tip: Get the Google Translate app. It translates text in photos and can even translate live as you point the camera at a text like a restaurant menu.

Owning stuff will become challenging

The amount of luggage you can travel with is limited.

So what to do with all the thick warm clothes and snow boots from your previous stay when moving to Bali? And where to store your snowboard while you’re there? Over time you’ll want to buy things that are useful only in certain places, but you don’t want to take them with you all the time.

There’s no good solution for storing your infrequently used stuff.

Tip: Try second hand. Maybe you’ll like it.

Tip: Ask local friends if you can store something at their place until your next visit.

You can have a negative impact on the environment

Aviation

Digital Nomads often take way more flights on average than people who only travel for vacation and business. Such a lifestyle inevitably leads to a bad carbon footprint unless we take measures to reduce and/or compensate for the emitted CO₂.

Tip: You can “offset” your emissions with charities like Cool Earth. It’s not ideal, but it’s a start.

Tip: Direct flights cause fewer emissions than multi-stop flights. Taking the train is better than a local flight. Less flying, in general, is better.

Infrastructure

Property development has increased significantly, landscapes are changing, and prices are rising. Traffic keeps getting worse, and public transit can’t keep up either. This is a problem with tourism in general, but more so in destinations like Canggu in Bali which is especially popular with Digital Nomads.

When I talk with Digital Nomads who’ve been to Canggu or Ubud, I keep hearing the same impressions:

Bali is beautiful, well-equipped for Digital Nomads, and there are great people around… BUT… The village is changing fast, losing its authenticity, and likely won’t be a paradise for long anymore.

Now that I’m finally here, I can see what they mean.

Tip: Avoid individual transport like cars and scooters if possible. Walk a lot or take a bicycle. Fall back to public transit or e-scooters if needed and available.

Gentrification

In many places, Digital Nomads can afford accommodations, cafés, restaurants, and groceries that are very expensive by local measures. Therefore, the locals rarely visit such places. Local places start making room for more expensive ones as they are more profitable.

Unfortunately, in many cases, only very little of the profit stays in the local area as business owners are often located in wealthier regions or countries.

Tip: Don’t only visit the places that cater to tourists and Digital Nomads. Explore local cafés and restaurants and also buy groceries in the small local stores.

Tip: Inform yourself about local tipping customs. Tip generously in low-cost regions.

Business occupation

It’s not uncommon to see Digital Nomads working for hours from the same café or restaurant. If they only order a drink or two — as unfortunately is often the case — you can imagine how little money the business must make per hour and table. Most businesses lose money by such behavior.

Even worse, there may be no free tables left for regular customers. These are the customers that sustain such businesses. The smaller a place is, the more severe an impact Digital Nomads have on its revenue.

Businesses must react, and they do that in two ways: Either raise the prices or simply don’t allow customers to work from their place. The former explains why such popular cafés have costly coffee. You’re paying for an extended stay.

Tip: Order multiple times to make up for all the time you’ve spent at a place. Tip generously.

Tip: Minimize your impact by occupying only the smallest available table. Stay clear of such places during rush hours.

Conclusion

Don’t trust social media blindly. Digital Nomadism is not for everyone. Explore, test, learn, and repeat in your own way.

Don’t get discouraged by the downsides. Most of them are under your control, if you’re aware of them and prepare accordingly. Over time, the upsides can far outweigh all of them.

Just like with any other lifestyle, there are pros and cons to being a Digital Nomad. Learning to handle and minimize the downsides takes time and experience. Ultimately it’s up to you to find out if it’s a way of life that you love.


There are also a lot of misconceptions about Digital Nomadism. The next article will address some of them.

Continue reading in Part 6: Misconceptions.

Marc Knaup

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❤️ building things, breaking things, writing software, discovering electronic music, living everywhere, and learning about life — knaup.io