Try Before You Fly: Auditioning Your Digital Nomad Destination


Let’s say you have the skills to work anywhere in the world. Where would you go?

Try Before You Fly: Auditioning Your Digital Nomad Destination

Let’s say you have the skills to work anywhere in the world. Where would you go? Some people would immediately choose their favorite travel destination. Others buy a ticket to a place they have always wanted to visit. Caveat: Once they arrive and try to set up shop, they might get a rude awakening: Their fantasy haven does not support the digitally nomadic lifestyle.

Since the digital nomad lifestyle implies a transitory state, some people take a c’est la vie attitude about digital destination disappointment. On the other hand, the inability to work usually means an inability to make money. And lack of money might prevent you from traveling to your next destination. Before you commit to a new working destination, give it a trial run.

Spontaneity vs Planning

I’m hearing a collective moan from all corners of the globe:

“Planning? That ruins all the fun! I want an adventure!”

Claro, as we say in Uruguay! Indeed, a thin line separates spontaneity and over planning. For shorter stays, of, let’s say, one month or less, it’s okay to seize the day and see what happens. But for anything longer, you need to consider a variety of factors. First, you must remember this: The idea of the Digital Nomad Nirvana is a myth.

But while no place is absolutely ideal, certain qualities make them deal breakers. Before you commit to a longer stay, give your targeted destination a two or three-week “audition.” During that time, attempt to do some work. Eat like a local. Stay out of the restaurants and shop at the markets and supermarkets. Take public transportation. You’re not a tourist. You’re a potential resident.

Visiting as a Tourist vs. Visiting as a Potential Resident

The old cliché, “It’s a nice place to visit, but I wouldn’t want to live there” is relevant to digital nomads. Visitors often see a glorified version of their targeted destination. Digital nomads need to take off the rose-colored glasses and face reality. Here are some issues to explore during your destination audition.

Wi-Fi Costs and Speed

During the last time you saw Paris, you might have stayed at a hotel that had excellent, free wifi. Or, perhaps you tweeted from one the city’s many WI-fi hotspots. But how good is it, and how much will it cost in a neighborhood where you could afford to live? Important: Do not rely on forums and social media posts for the answer to this question. You need to rent temporary housing, and see for yourself.

In addition to the WI-fi speed and costs in your apartment, it’s important to check the availability of Internet cafes and coworking spaces. One of the biggest mistakes that digital nomads make is assuming that their freedom of work-style frees them from deadline obligations. Not so. Your clients don’t want to know about your computer crashes. If this happens, make sure that you have easy access to Internet cafes and coworking spaces.

Safe, Affordable Housing

Internet access is just one reason to choose an apartment over a hotel. Apartments let you explore the residential neighborhoods, and identify issues such as safety, cleanliness and affordability. If you have kids, you will also want to explore the local schools. Then, there’s the issue of your actual living space. Here’s a hypothetical situation:

Let’s say, during your last visit to Uruguay, you stayed at the Hilton Hotel in Punta del Este. Hopefully you didn’t, but that’s a whole other topic for discussion. You liked Uruguay so much that you decide to make it your next digital nomad destination.

So you sign a one-year lease on an apartment. Then, much to your dismay, you discover that many of the affordable Uruguayan apartments have a serious mold problem, and you are drastically allergic to mold. Now you’re stuck with a one year lease. If you had taken a short, exploratory trip, you would have learned this right away.

Continuing to use Uruguay as an example, it’s important to define how different countries define “unfurnished apartment.” In Uruguay, and in many other countries throughout the world, it means:

  • A kitchen sink
  • A toilet, and maybe a bidet
  • A shower, but almost never a bathtub

And that’s it. In other words, you need to buy your own water heater, refrigerator, oven and furniture. This is a really bad idea for digital nomads, who only plan a short stay at their chosen location. And speaking of how long you plan to stay, let’s talk about how long you actually can stay.

Visas, Residencies and Reciprocity Fees

This section only applies to digital nomads planning to work overseas. Before you go, you need to determine:

  1. Whether you need a visa
  2. How long you can stay
  3. Whether you targeted location will require you to pay a reciprocity fee.
  4. Is it possible to apply for residency? If so, how difficult is the process?
  5. What are the health care options for digital nomads? Note: This might also apply to nomads traveling within their own country. For example, if you are on a state health plan, such as Cover Colorado, they might not cover you if you are temporarily living in a different state.

Although some of this information is available online, things are rapidly changing. A country that did not have a reciprocity fee might suddenly decide that they need one. Or the opposite can happen, as is the case for Chile.

Final Words

This article covered many details, but these are the most important factors:

  • Do you feel happy, safe and healthy here
  • Are you able to do some work here, without interruptions such as poor Internet access, laptop thefts, etc.
  • Does the place inspire you to work? Does it give you new ideas?
  • Does your target destination attract specific types of clients? This is especially important for travel writers.

If you answered “yes” to these questions, pack your bag, and prepare for an exciting journey. To quote Walt Whitman:

“The untold want by life and land ne’er granted,

Now, voyager, sail thou forth, to seek and find.”

This post was penned by...

Lisa Marie Mercer

From the heart of New York City, to the hill towns of Italy, to the ski towns of Colorado, to the beach towns of coastal Uruguay, Lisa Marie Mercer has journeyed across the globe, often stopping to stay a few months or a few years. A widely-published writer, she covers topics such as travel, expat living, health and fitness, skiing, social media, Latin America and startup entrepreneurs.

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