Between September 2016 and February 2018, I traveled through the Americas as a digital nomad. I usually try to avoid using this term because one may get the wrong idea of what it means when watching certain YouTube videos or Instagram pictures. Or just simply google it. Chilling out in a hammock on the beach on a sunny day with your laptop on your lap drinking your $10 margarita while getting a foot massage really doesn’t work and does not represent the lifestyle.

Instead, terms like ‘location independent professional’ or ‘remote worker’ aren’t likely to become buzzwords any time soon, which is a good thing. When I think of a stereotype digital nomad, I think of the guy with the interesting beard working casually on his Apple computer in a Starbucks. When I think of a remote worker, I think of a person working from a co-working space during regular office hours. Personally I don’t care how you name it, but there are people who may be wary of working with the hippies of the 21st century.

How you handle this new type of freedom of working wherever and whenever you want will determine the perception of the people you work for and with. I am sure Mr. Weird Beard is an expert in what he does and is a total professional, but people may not know that (yet). I feel that many people still see a digital nomad as a glorified backpacker that travels to cheap countries and does a freelance gig every now and then to pay the bills. In order to avoid having that kind of conversation with a prospect I will just say I am not (or don’t want to be) bound to one location to be able to do my job.

In what follows is my story before, during and after my 17 month trip across the Americas. After a month in Belgium I got back to traveling Europe and Asia, so I will compare my experience between these three continents as well. It is my hope that you find some inspiration in my story to help you become a remote worker.

How It all came together

I am a freelance software architect specialized in building complex and large-scale web applications. Before I worked at large consulting firms for nearly three years. Due to low job satisfaction, my co-workers encouraged me to make the move. They told me I was at the right age (I was 25 years old at the time), had the skills and the right mindset to make it as an independent consultant. So somewhere halfway 2015 I resigned for the second time in just a few months, and started looking for projects for my new business. It didn’t take long before things started to take off.

In my experience, the easiest way to find a job as a freelancer (in my field) is via recruiters, who typically are contracted by rather large and well-established organizations to look for a matching profile. The assignments they have in store are roughly the same (i.e. making some software for internal use) and last well over a year. It’s not terribly exciting but you get a challenging and stable job and the pay isn’t too bad either. One note of warning: carefully choose the recruiters you work with. I found many of them to be sloppy or careless. The last thing you want is to them to present you to a company you’ve already applied for.

However, from time to time some interesting projects come across my virtual desk. Lucky for me, the very first opportunity that I was introduced to was one of those. The type of job and company were exactly what I was looking for. I signed the contract the same week and we’re still working together at this date after three years. They gave me the freedom and confidence to work on an exciting product that is being used by interesting companies all around the world. However, their willingness is only part of the equation. You also need to establish a working environment in which remote work is possible. Before I left for Latin America, I already worked from home a lot and that worked very well. Add an agile methodology and a series of tools and communication channels to the mix and you have yourself a digital company which allows people to work remotely.

I realize that many other freelancers don’t have this kind of stability so they have to go from job to job trying to make ends meet. That alone can be stressful enough, so can you image doing that when you are always on the move? Digital nomads are usually seasoned travelers but even so, the constant traveling has a serious impact on your state of mind. I will come back to this later.

Where I have been

During my 17 month trip, I visited 15 countries on the American continent (see map below).

I began my trip in Peru and went all the way south to the end of the world in Ushuaia. After an excellent stay in Buenos Aires I made my way up to Central and North America to ultimately finish my trip in New York City.

I would usually stay in each place for about three to four weeks, but because I did not have a fixed schedule I ended up staying in some places much longer than expected (and skipped other places). For instance I ended up staying in Playa del Carmen for more than three months which I never expected. Not planning everything in advance is a great piece of advice as things will go wrong that will mess up your planning on trips like these. Combined with the art of slow travel and you get a lifestyle that can’t be beaten.

One of the (unplanned) upsides of my trip is that I managed to avoid high season in most places but sometimes that came at a price. For instance there was the extreme humidity in the Caribbean in the middle of hurricane season or the blizzard on the east coast of Canada and the USA. I’m happy to accept that if that also means beating the crowds.

What makes a good digital nomad destination

When it comes to destinations for digital nomads in Latin America, these are the most popular:

  • Buenos Aires, Argentina
  • Medellín, Colombia
  • Antigua Guatemala, Guatemala
  • Playa del Carmen, Mexico

I can see why they are so popular but to be honest, I only truly liked Buenos Aires and Antigua Guatemala. Buenos Aires is one of the world’s greatest cities and I can see myself living there. In contrast, I got bored in Medellín and Playa del Carmen is a touristy beach town filled with snow birds from Canada and the United States. But both places have a great vibe and it’s easy to meet new people (both locals and gringos). If you plan to go there – which I recommend – but be informed before going (which I was not) and manage your expectations accordingly.

In order to qualify as a good digital nomad destination, the following requirements should be met:

  • WiFi
  • Cost of living
  • Activities
  • Weather
  • Safety

Websites such as Nomad List have many more parameters but the ones I listed here are pretty much the basics. For a digital nomad it is essential to have a stable and fast internet connection. Let’s take Sucre, Bolivia as an example: during my two week stay I had to go from cafe to cafe just to find a decent connection. Such a shame because it is a fabulous city!

Secondly the cost of living is another obvious requirement. The money I spent in Los Angeles, Toronto and New York city during low season in three weeks time was the same as a three or four month stay in South America. For many nomads this is a deal breaker as they often make less money as they would with a regular job at home, which is why they tend to go to Asia or Latin America as it is generally speaking cheaper than countries in the western world. After my trips to Asia I found that Asia offers better value for money than many places in Latin America!

The next two requirements are mostly relevant for the weekends: good weather and activities. The first six months of my trip I went hiking pretty much every weekend, and in the second leg I went diving a lot. In the big cities I like to go to the theatre, visit museums, go to cafes and just wander around, absorbing the atmosphere.

A city that lacks accessibility to nature or culture is not a good destination. For instance I went scuba diving every day in Santa Marta, Colombia. Even though the city itself was disappointing and rather ugly, I had a great time underwater learning new scuba diving skills. People who don’t like diving would probably be very disappointed by the city. Having things to look forward to for the weekends had a surprisingly big impact on my motivation during week days.

And lastly there is safety. It is such a cliché but it is ever so important for a digital nomad who carries many valuable items – and basically his whole life – in one bag. As far as South and Central America goes I think it is safer than ever to travel there. Safety was never on my mind when I was looking for the next place to go. Having said that I was mugged once in Colombia but it was my mostly my fault anyway.

Keeping these requirements in mind, I would consider the following places as my top picks (with a few caveats):

  • Cuzco, Peru : beautiful city with a lot of history and so many outdoor activities. However it gets pretty cold at night – which is normal given you’re 3500 meters above sea level – and the internet connection can be spotty (I worked two weeks from Starbucks).
  • Arequipa, Peru : charming colonial town with pleasant temperatures and a spectacular view of the El Misti volcano. Not too far from here is Colca Canyon and it’s only a three hour bus ride to Lake Titicaca so it has a great location. As far as I know there is no expat community (Starbucks would be your best pick again) but it’s perfect for a two or three week stay.
  • Sucre, Bolivia : I had to include this one even though the internet connection is unstable at best. But it’s so pretty and pleasant. The weather is Mediterranean, the people are friendly, great Spanish schools and the food is surprisingly good.
  • Bariloche, Argentina : extremely beautiful area with lots of outdoor activities. It can be a bit pricey (being in the south of Argentina) and the town isn’t that exciting.
  • El Calafate, Argentina : same pros and cons as Bariloche. The Perito Moreno Glacier is the least exciting thing around. A mere 215 kilometer away – or the first nearby village – is El Chaltén, also known as Argentina’s hiking capital.
  • Cuenca, Ecuador : very pleasant colonial and university town with lovely temperatures and fast internet. Very similar to Sucre and Arequipa. The main difference is the heaps of Americans retiring here so the vibe was slightly less exciting than the other two towns mentioned.
  • Antigua Guatemala, Guatemala : beautiful city that seem to cater to the Americans. Apparently it is known as a great place to learn Spanish. It is bizar to see fast-food chains in beautiful colonial buildings in a city that is otherwise soaked in history. Guatemaltecos are among the friendliest people in the world and the Mayan culture is still alive and well.
  • Lago Atitlan, Guatemala : possibly one of my favourite places in the world. Surprisingly modern facilities for being so remote. I booked a fantastic house which only made things better (see the Goats on the Road video and you’ll understand)
  • Guanajuato, Mexico : beautiful city but it gets cold at night if you live on the wrong side of the valley and Mexicans are not the best neighbours (and their dogs bark at literally anything for the majority of the day) when you want work from home. Foreign tourists seem to prefer the nearby San Miguel de Allende, leaving you all alone with the Mexicans in a lovely city. If Guanajuato were in Europe, it’d be one of the most popular places on the continent.

At the other end of the spectrum, I would not recommend the following places:

  • Ambergris Caye, Belize : fantastic diving but very expensive, WiFi is bad and the people are not concerned about environmental conservation at all.
  • Havana, Cuba : non-stop harassment from the locals made my stay miserable. And WiFi is pretty much non existent.
  • Galápagos Islands, Ecuador : spectacular place and significant spot on Earth, but if you’re going there don’t work but take some time off to enjoy the islands. It’s also rather expensive and the WiFi connection wasn’t great.
  • Panama City, Panama : a modern city with good internet but it was rather dull when I was there.

Traveling in the Americas

Traveling in between cities and countries turned out to be surprisingly easy. Of course, I stayed in ‘civilized’ places where airports are nearby and WiFi is prevalent. There are still enough places that are difficult to reach so adventurers don’t need to worry about taking the less traveled route! The only time I can remember having an uncomfortable trip was – unsurprisingly – the flight from Cancún to Havana. But overall I had a great experience with airports and airlines in Latin and Central America. I don’t know if it is a coincidence but I was allocated a seat in the emergency exit row for every Avianca flight. No complaints there! The airlines in North America however aren’t as good as their counterparts in the Spanish speaking part of the continent. The lines are longer, the staff isn’t as friendly, the rules are much more strict, it’s more expensive and you get less value overall.

The good news show continues when it comes to accommodation. In this day and age pretty much everything can be done online which makes traveling almost too easy. I booked the majority of my accommodation on AirBnb, which makes perfect sense for people who are staying in one place for weeks or even months. Lodging in hotels would almost certainly break the bank and they just don’t provide the same comfort as apartments. A generally cheaper alternative to AirBnb is to find accommodation on local sites or Facebook groups. Although it’s much cheaper it’s also more of a hassle. I’m not a very patient man so I stuck with AirBnb and had a very good experience. But prices are rapidly increasing, yielding a much lower value than a couple of years ago, so it might be interesting to find alternative ways of finding accommodation.

The word is still out on the legality of digital nomadism so you may have to be a bit creative at times. For instance, in order to avoid trouble at the border I always declared to travel as a tourist. Technically I never worked with or for a local organization so a business visa wouldn’t have made sense. Even it were illegal, digital nomads can bring in a lot of money for the local economy. They make ‘western world’ money but they spend it locally and that seems like a pure win-win situation to me (There are people who strongly disagree with me on this statement and they may have a point. It is an ethical question that should be discussed). As long as there isn’t a clear international regulation, I’d recommend you to stay quiet about the whole digital nomad thing to the immigration officers and travel on the tourist visa.

One thing I did have problems with was the proof of onward travel requirement upon entry. In most Latin American countries you need to show proof that you will leave the country (bus or plane ticket) but according to the internet this rule is never enforced by the airlines and the immigration officers. I can assure you this is enforced by both. Once I was even questioned by an army of angry looking officers in a sketchy office in Buenos Aires (I charmed my way out of it by using some Argentine slang words). One trick is to use services such as BestOnwardTicket (FlyOnward seems to be out of business).

How does it compare to Europe and Asia?

Europe

Even before I started my career I traveled quite a bit in Europe. It’s chock-a-block with fantastic cities and everything is so organized which makes travel the easiest. There are heaps of low cost airlines and the train network is actually useful. In fact, if you have the time I believe travel by train may be the best way to get around in Europe (I suggest you check out the Eurail or Interrail pass if you’re interested).

You’re spoilt for choice when choosing destinations in Europe. There are the usual suspects like London, Paris, Rome, Amsterdam but they are already overrun by tourists. In fact, most of Europe suffers from over-tourism. As a result, rent and short-term accommodation have gone up quite a bit in my experience. Certain parts of Europe (the Balkans and Baltic countries for example) are still developing their tourist industry so you still may find some gems there but it’s changing quickly. I went to Croatia in 2011 and by 2014 the tourists had also discovered the thousands of kilometers of sunny – albeit rocky – beaches and historical cities.

The beautiful thing about Europe is its diversity. I once had the privilege of overhearing a conversation between a Fin and a Italian guy from Napoli. One guy was quite and polite where the other seemed to be performing an act of Romeo and Juliet when he was talking. They are both so different but they share the same values and principles. Maybe that’s why it’s easier to blend in with the rest than any Asian country (where I found the culture gap enormous). Latin American countries like Argentina, Chile and Uruguay are in that respect very similar to Europe as I made some good friends there.

Asia

It took me 28 years to travel to Asia, unless you consider central Turkey part of Europe. Seems to be a delicate question with many different answers. I started out with the easiest and most obvious destinations: Chiang Mai and Bali. I found Chiang Mai a rather sad place. Retired westerners on the other hand seem to have the time of their lives and they don’t seem to mind the attention from the Thai women who don’t even deny they are out for their money.

In contrast, I absolutely loved Bali. The people are so friendly and the island is pleasant with a bunch of things to do, despite the presence of holiday makers. I liked it so much I even had a little weep on my last night, which should be proof enough that it’s a fantastic destination for anyone.

I am not yet convinced of Asia’s charm even though it has better food, the weather is more pleasant, it’s cheaper and in general also safer than Latin America’s counterparts. Asia seems to be more accessible for various types of visitors, whereas Latin America is more a place for adventurous people. Like I mentioned  before, I found the cultural differences much bigger than anticipated. There is the obvious language barrier but I found it hard to connect with the locals, even with those who do speak English. And then I’ve been to quite touristic places so I’m already looking forward to going to less explored parts of Asia!

Maybe I should travel a bit more in this part of the world to appreciate its people even more but if I had to do my trip over again, I’d still pick Latin America in a jiffy.

A day in the life

Now let’s have a look at a day in the life of a remote worker. To be honest it’s not that different from a ‘normal’ day. The things you do at home are still part of the routine abroad: going to the gym, buying groceries, going for beers after work, etc. Nothing really changes either when it comes to work: my contract remained the same which states a 40 hour working week.

The only major change is where I worked from. North Americans don’t even have to worry about time zones when living in Central or Latin America, but Europeans have to take into account there may be a 4 to 7 hour time zone difference – if their clients are situated there obviously. Having to be available during European business hours is a factor that can be issue if you don’t talk this through with your clients.

Fortunately for me, communication with my client has been a doddle. Every other day we had a Skype meeting during which we discussed ongoing work. There are other channels in which we communicated (e.g. Microsoft Teams or our issue tracker). It’s thanks to these technologies that we can live and work at the other side of the world and still be just as productive and effective (maybe even more so). Any organization that is more or less mature already has these things in place so the investment of enabling remote work shouldn’t be a big one.

I prefer to work in places without many distractions. That usually means working from home or from co-working spaces. Sometimes I go to coffee houses but that is rather exceptional – except on Sunday mornings when I occasionally work on my pet projects. Besides, with all my equipment it isn’t a great sight to behold (Apple fanboys on the other hand are right at home in coffee houses).

Anyway it doesn’t really matter where you work as long as there is WiFi. It doesn’t even have to be quiet but that only works because I bring a life-saving item: noise cancelling headphones. Latinos – bless them – are pretty loud people so my headphones have helped me out on many occasions. It’s an item that won’t disappear from my must-haves list any time soon.

I don’t usually work in the weekends (and if I do it’s mostly non-billable work) so that gives me time to do fun activities. As I wrote earlier, I like outdoor adventures, which is something easily found here. Latin America has fantastic hiking trails. I particularly enjoyed hiking in Patagonia and Peru. Central America has some some world-class dive sites. My favourite dives were Half Moon Caye (Belize) and Cozumel (Mexico) but there are much more, such as Roatán and the Bahamas.

In between all the outdoor action, I also took the time to take postcard pictures at the typical tourist destinations (Machu Picchu, Iguazu Falls, Chichen Itza, etc.) living by the philosophy ‘while you’re there you might as well do it’. During my free time on working days I would also take Spanish classes. Weirdly, you don’t always get (the chance) to practice it on a daily basis as the locals seem to want to practice their English. Or they just assumed a white person doesn’t speak Castellano, which became annoying after a while. Fortunately in the smaller cities – which I already liked – people were less inclined to speak English so my Spanish got a lot better in those places.

What makes a good digital nomad

From the people who I have met and from my own experience, there are a few characteristics that will help you in being (and staying) a good digital nomad:

  • Passion: when I hear people talk about their business and their projects, you can feel the passion. Some were being plain geeky while others had noble and idealistic goals, but everybody was working towards something to make the world a better place.
  • Discipline: it is easy to get distracted with all those new places and people that surround you. Sometimes you just want to go paddle boarding but you have to push on through to keep your projects on track and your clients happy.
  • Skills: the people I have met on my trip were all very intelligent people with a certain skill set. Many of them had technical skills (engineers, SEO specialists, developers, etc.) but there were others who were projects managers overseeing people from all over the world. As long as you have some useful and marketable (preferably high in demand) skills you can be a digital nomad.
  • Transparency: Communicating clearly and effectively is even more important when you’re abroad. It helps in building trust with the client.

Next to these traits it is recommended to be active in a field that doesn’t (always) require your physical presence and/or a lot of interaction with other people. Software developers make a great case. For a project manager it is a tad trickier although it’s still certainly possible given the right circumstances. The other nomads that I met usually worked in technology (developers, architects, SEO specialists, consultants, IT support,etc..) but I also met a number of entrepreneurs, writers, translators, regional managers, professional poker players, etc.

The challenges

One of the main issues I am having with the nomadic lifestyle is that people make it seem that the world is all sunshine and rainbows but it really isn’t. What goes beyond the stunning photos and videos is a different story that few people get to hear. Or should I say what people want to hear? Everybody prefers a happy story over a sad story right?All the good things that come with the lifestyle come at a price and they may have devastating effects on your psyche.

Social isolation and loneliness

After a short break from the Americas I continued my adventures in Europe and Asia. And then it hit me: I was never really part of the community unless I lived there for a longer time (let’s say 2 months or more). During my stay in Seville I met a few interesting people who took me everywhere but there were enough occasions where I just wandered around town just to see the locals having a great time in the many bars and restaurants. I never noticed it before (maybe because I was doing more activities in the weekends) but once I had it was (and still is) hard to get it out of my system. Loneliness is a serious issue and it got me depressed for months.

Sleep

Waking up in a different bed every few weeks (or more frequently) has a detrimental effect on your sleep. One day you sleep in an extremely comfortable bed on the shores of a lake where at other times you seem to wake up in the middle of a busy roundabout. I am not an scientist but I am fairly sure that’s a bad idea for many reasons.

Limbo

Somewhere I read a comment from somebody who tried to describe what it’s like to be traveling non-stop for years. He wrote about being in a state of limbo and I thought he or she made an excellent point. While the travel & work thing is the whole point of being a digital nomad, you are fully committed to your work while you try to travel in between. This leaves little freedom as clients expect you to make meetings and deliver results, so you can’t be really impulsive and go paddle boarding instead of fixing a nasty bug that’s been annoying you for the last four hours. That is unless you run your own business or work in a different field but then you run into different kinds of problems and challenges. Even though you are not limited to your home of office any more, you are still ‘trapped’ in the world you thought you escaped from.

Costs

An argument that is always given on why you should become a digital nomad is that living abroad is cheaper. If you travel like me and you are not from a place like the Bay Area then the costs in Latin America may not necessarily be cheaper. Many South American countries have suffered from high inflation and prices probably never have dropped. In that respect, Asia is the clear winner.

Final thoughts

Being able to travel and work simultaneously is something I have dreamed of for years. You get to see the world and go to places you want to be whilst you maintain your job and be (and feel) useful to society. You create so many memories with the people you meet and by the things you do. Being a remote worker is exciting but it is not without its downsides. Loneliness and anxiety can have serious consequences for your mental health if not handled properly.

Once you start living the dream, it’s no longer a dream. It becomes your reality, and nothing is perfect in the real world. So be careful what you wish for, because your life may become unpleasant if you’re not careful.

People are usually quite enthusiastic when they hear my story. When the conversation continues, they would tell me why they couldn’t do the same thing. But anyone with an idea or skill has the potential of living a remote life. There will almost never be a perfect time to start a new business or convince your boss to allow more remote work, so my advice would be to get cracking now if you want to have a stab at it and be persistent.

Some random (fun) facts

Here are some fun facts and statistics of my trip:

  • Countries visited: 15
  • Flights: 37
  • Missed flights: 2
  • Days abroad: 516 (September 8, 2016 – February 4, 2018)
  • Dives during this trip: 70
  • Times mugged: 1
  • Highest point: 6088 meters (Huayna Potosí)
  • Lowest point: -37 meters (Santa Marta)
  • Most southernly point: Ushuaia, Argentina
  • Most northern point: Toronto, Canada
  • Warmest temperature: 40 C
  • Coldest temperature: any Colombian bus

 

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