Feeling Connected Outside of the Cubicle: The Challenge of Telecommuting While Traveling

To be a remote worker is to be at the forefront of the evolving nature of relationships, where a shared geography isn’t the glue it once was. Working from home or the road has many benefits, but it costs you face-time with other humans in a world that’s already a little too disconnected.

While forward thinking companies are designing offices that help their employees interact in meaningful ways, remote workers are often left adrift, and too often the extra freedom a remote worker enjoys is turned inward instead of outward.

How do you recreate the nomad-equivalent of smart workplace design? When there’s no more water-cooler talk, how do you escape your echo chamber and make new connections?

Seek Out Long Stays

Especially when first starting out, a lot of remote workers get itchy feet, building themselves city-hopping itineraries better suited for gap-year students than full time contractors. That method can lead to burnout.

To avoid the burnout (or to find a place to alleviate it), consider settling down in a city that allows for longer-term visa-free stays. Even if it’s only for a few months, the connections you make during that time may turn it into a place you return to again and again.

Locals in digital nomad hotspots have seen people come and go before, and, as such, there’s a bit of a forcefield you have to break through to get to something resembling true friendship. But return to a place you’ve been before, and you’ll show the people there that you’re not just some tourist; you’re a location-independent worker, and of all the places you could be, you’ve decided to return to the place they call home.

Several countries allow visa-free stays of three months or more for US citizens. Many of them aren’t the traditional tourist hotspots, and that’s a good thing. Here’s a short list:

  • Albania (12 months)
  • Argentina (3 months)
  • Bahamas (8 months)
  • Belize (6 months)
  • European Union (3 months)
  • Georgia (12 months)
  • Japan (3 months)
  • Mexico (6 months)
  • Peru (6 months)
  • Serbia (3 months)
  • South Korea (3 months)


Not everyone feels comfortable staying in a hostel. And, to be fair, not all hostels are great places to stay. But when it comes to social collisions in a foreign city, there are few better places to start. The constant flow of international guests can be an invaluable resource for finding housing, tours, tips, and next destinations.

Most people are only passing through, but the secondary connections you can make may end up lasting much longer. Do your research beforehand, and look for well-reviewed hostels with a high maximum occupancy. Even if you don’t stay in the hostel as a guest, they usually have open social spaces where meeting new people isn’t just possible, it’s the entire point.

Coworking Spaces

Coworking spaces are the unofficial embassies of the remote worker, where everyone’s on more or less the same page, and they’re an important arrow in your quiver for keeping connected as a stranger in a strange place.

Most cities will have more than one, so go for test drives before settling on a month-long membership. Look for one that counts both locals and nomads among its clientele. Most coworking spaces will offer events that are geared towards a mix of socialization and networking. But the most critical feature is universal to all: in a coworking space, the approachability levels are set to high. Just because you busted out of the cubicle doesn’t mean you can’t rent a desk and play office for a little while.

Say Hello

Even if you’re an introvert by default, take heart in the fact that, as a traveler, you have far more reasons to approach people than you would at home. And, by the same token, people have more reasons to receive you warmly.

A little curiosity goes a long way. So ask questions. Admit your ignorance. Ask for help, and offer it in turn. Give compliments freely. Smile. Say yes. It may sound cliche, but it works. Your comfort zone is the enemy. Avoid it, and you’ll be exposed to more people with more diverse viewpoints than you ever imagined.

Some of the people you meet will turn out to be friends you keep over many years, across great distances. And the activities they invite you to—a cooking class, a hike, a language class, a yoga session—could become hobbies you carry with you on further travels.

Get Social (Media)

Even if you carry a tinfoil hat in your backpack, set up at least one account on a major social media network. On Facebook, practically every major city has a group for expats, freelancers, or digital nomads, where you’ll find meetups, tours, and advice. Instagram is the traveler’s business card: a way to establish some trust and also stay in touch. Sure, your data may be harvested and sold to nefarious shadow brokers. But you’ll also know who’s doing what, and where, allowing you to connect in person or ask and answer questions about a different place altogether.

Form a Routine

Relationships are built on repetition. So even though you’ve busted out of the cubicle, there are benefits to forming a routine. It doesn’t have to be a strict nine-to-five you spend in a single place, but try to pick a few favorite settings and visit them with some regularity. Give the people there a chance to get used to you. A particular coworking space, cafe, or bar might seem more closed-off than you’d like, at first; but if you keep going back, you’ll gradually notice smiles and greetings as you become a fixture in that environment.

Reach Out

Everyone knows that as you get older, staying connected takes proactive work. That workload is doubled when you go location-independent, as you’ve effectively taken yourself out of the physical loop. While you’ll be expending plenty of effort on meeting new people, you can’t neglect the friends you’ve already made. To stay connected, you’ll need to take an active role in maintaining the relationships you want to see maintained.

  • Schedule Skype Calls, Facebook or WhatsApp Video Chats, or Google Hangouts. There’s no substitute for speaking face to face (even if it is through a screen). While it can feel a little awkward to schedule a time to talk about nothing in particular, time zone logistics often make it a necessity. Don’t worry if a few appointments fall through. When it finally works, a smile fixes everything.
  • Send Email Updates. Especially when you first start out, everything can feel newsworthy. Try to condense it into emails for your close friends and family, say once a month. It might seem a little narcissistic at first, but it’s not; the people who care about you are interested in your life, and by putting it in an email, you clear bandwidth to talk about the other person when you do connect one-to-one.
  • Utilize Your Network. The people you meet along the way are a precious resource for gaining intel on new locations, and you’re a precious resource to others in the same way. Look for opportunities to help other people connect to each other, and make yourself available to answer questions.
  • Make Excuses to Interact. Play fantasy football with your friends back home? Don’t give it up; win the league. See a reference to your friend’s favorite TV show? Send them a note. Consider it a postcard: just thinking of you. Some people might have the idea that in your non-traditional work situation, you have no room for the people you know still back in their cubicle. Prove them wrong.

Connect with Yourself

Connecting with people outside the cubicle can feel like a second job. A fun job, but a job nonetheless. To avoid burnout, you have to make time to connect with yourself. Physical activity (gym, yoga, running, cycling) has mental benefits. Journaling orders your thoughts and schedules your time. And even though your friends at home might think your life is one long vacation, don’t neglect the opportunity to take an actual break. Group tours can be a great way to connect with other people, but a solo tour can be the retreat you need to refuel your batteries and stay connected to yourself.


Matt Zbrog
Matt Zbrog

Matt Zbrog is a writer and freelancer who has been living abroad since 2016. His nonfiction has been published by Euromaidan Press, Cirrus Gallery, and Our Thursday. Both his writing and his experience abroad are shaped by seeking out alternative lifestyles and counterculture movements, especially in developing nations. You can follow his travels through Eastern Europe and Central Asia on Instagram at @weirdviewmirror. He’s recently finished his second novel, and is in no hurry to publish it.

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