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By The Way
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I’ve worked remotely from 14 countries. Here’s what I learned.

Consider my lessons your beginner’s guide to being a digital nomad

Catching the last of the afternoon light on the balcony of an Airbnb in the trendy Palermo Hollywood neighborhood of Buenos Aires. (Photos by Peter Hershey for The Washington Post)

The reality of traveling while working is that your time is not your own.

Sure, a fully remote setup means that you can be lounging beachside in Ecuador while firing off Slack messages, but at the end of the day, you still have to crunch those numbers or write those TPS reports. It’s like vacation — but with a few strings attached.

My digital nomad journey started in summer 2021. I was a user-experience designer at The Washington Post and had the luxury of a fully remote job at the time. Working from the D.C. office was still off-limits, global coronavirus cases were down and “hot vax summer” was in full swing. I knew the timing was right.

So, I ended my lease in D.C., sold my furniture and headed out on the road with nothing more than I could fit into a suitcase and a small backpack. It felt like a big step, but considering I was a city dweller with no car and not many possessions, the moving logistics were relatively straightforward.

Like summer camp for grown-ups: The pandemic is changing the digital nomad scene

A year and a job change later, I’ve worked remotely from 14 countries across two different continents. I feel profoundly grateful for the experience. I recognize that it’s not a luxury many have, but I believe the lifestyle is more attainable than some remote workers may think. Take these lessons I’ve learned as an accessible starting point for your own digital nomad journey.

Read all the requirements — twice

Read, then reread all the entry requirements for every country you plan to enter.

This might seem obvious, but in the age of the coronavirus, public health regulations are always in flux — and can vary drastically from country to country. Tools such as Airheart’s coronavirus restrictions map are helpful for planning, but it’s always best to go straight to the source. Check the U.S. State Department’s travel advisories and your destination’s official government website before booking anything.

Because I didn’t spend more than a month in any one country, I didn’t need a digital nomad visa. My experience was more like long-term tourism rather than a full-on relocation. But some countries require a visa depending on your length of stay, so be sure to check.

What it's like to be a digital nomad in Rio

And don’t forget to check for restrictions between countries on your itinerary. If you don’t read carefully, you could end up with canceled flights and an unexpected stay in Montenegro because Austria no longer accepts travelers from the Balkans.

Make the most of your time zone

Being a nomad means balancing your leisure time with your professional responsibilities. So, work with your schedule, not against it.

If you need to be online for East Coast hours, trying to work from Bali (12 hours ahead) will probably leave you exhausted. But you can fly to Machu Picchu without ever leaving your time zone.

Work mornings and explore the nightlife in the evenings, or work evenings and go hiking in the mornings; there are no right or wrong answers. The most important thing is communicating with your team to ensure you’re all on the same page about when you’ll be online. I’ve found that establishing these expectations early goes a long way, especially when problems arise.

Even if your job keeps you deskbound for most of the day, you can still explore spots close to your home base. When working from Medellín, Colombia, I was able to go paragliding on my lunch break, because I found a tour that would pick me up and drop me back home within the hour.

Home isn’t always where the WiFi is

As much as I want to work every day from a sunny cafe in Lisbon, sipping espresso and nibbling pastéis de nata, the reality is that working in public spaces has its downsides. And if you’ve ever tried taking a Zoom call in a crowded cafe, I’m sure you know them, too.

Plus, public WiFi networks — even ones with passwords — still pose a significant security risk, so a private network or VPN is always advisable for digital nomads. When hunting for Airbnbs to work from, search for terms such as “WiFi,” “connection” or “working remotely” in the reviews to weed out stays with a spotty connection.

Sometimes, though, using public WiFi is unavoidable. Take my trip to Bariloche, Argentina, in northern Patagonia, for example, when an unexpected snowstorm led to power outages and downed trees. Cut to me and a busload of people trudging through a mile of slush to reach town — and a stable connection. On the flip side, the cafe I worked from that afternoon, Vertiente Café con Ideas, was immensely cozy.

Be strategic about packing

Your priorities define your packing list. You can take anything you want, but you’ll have to lug it around, so choose wisely.

If you’ve ever explored the OneBag subreddit, you know there is an entire subculture around minimalist travel. And although I appreciate their principles (“more focus on the experience than the logistics”), I opt for a slightly more moderate approach.

Embrace overpacking: The case against carry-ons

I use the Minaal carry-on 3.0 as my main bag. It’s 35 liters, flattens into a pancake when it’s not full and has all the pockets I could ever need. I pair this bag with a cheap multiuse daypack that I picked up at the mall for $15. It’s easy to sling over my side or chest when I’m navigating through airports with both bags. Plus, the cheap, unassuming look makes it less of a target for thieves or pickpockets. Not everything has to be premium.

My personal rule of thumb is to pack enough clothes for one week, then do laundry as needed. This involves researching how to do laundry in each location where I’m staying. In Argentina, for example, it’s uncommon to find a self-service laundromat, but lavanderias where you can get clothes washed and pressed are seemingly on every corner.

Solo travel doesn’t have to be lonely

Not unless you want it to be.

For me, traveling solo is an almost-spiritual experience. There is nothing like the feeling of wandering the back streets of a new city — soaking in all the details that make this place feel different from home. I often curate city-wandering playlists for this very purpose, such as this one of Czech folk musicians and composers that I made for Prague.

That doesn’t mean there aren’t days — or even weeks — when I get lonely. When I start feeling this way, I find that the easiest way to refuel my extrovert tank is to attend gatherings of fellow travelers. I’m almost always able to find meetups by searching for “digital nomad” or “expat” groups on Facebook or Meetup.com. Try attending a language exchange to brush up on your skills or to help someone learn your native tongue.

But I would also encourage you to embrace the unique freedom that solo travel brings. Strike up a conversation with that person in line at the train station. You never know where it may lead.

My friend Renan and I were total strangers when we accidentally made eye contact in the Medellín airport; five minutes later, we were trading stories about our hometowns. (He’s from Brazil.) Fifteen minutes later, his translation skills were helping me out of a vaccine verification situation at the airline desk.

Two days later, we were in Santiago grabbing cervezas and completos (Chilean hot dogs) like old friends.

And you never know when a friend might come in handy.

Peter Hershey was formerly a UX designer at The Post and now works as an interaction designer at Google. He currently lives and works in San Francisco.

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