Digital nomadism: a beginner’s guide

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

Sure, a fully remote setup means you can lounge by the beach in Ecuador while messaging Slack, but ultimately you still have to calculate those numbers or write them down. GST reports. It’s like a vacation, but with some conditions.

My journey as a digital nomad began in the summer of 2021. I was a user experience designer at the Washington Post and had the luxury of fully remote work at the time. Working from the DC office was still prohibited, global covid cases were down, and “vax hot summer” was in full swing. I knew the time had come.

So I ended my lease in DC, sold my furniture, and hit the road with nothing more than I could fit in a suitcase and a small backpack. It seemed like a big step, but given that I was a city dweller with no car and few possessions, the logistics of moving were relatively simple.

Like an Adult Summer Camp: The Pandemic is Changing the Digital Nomad Scene

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

Read all requirements — twice

First, read and then re-read all entry requirements for each country you plan to enter.

It may seem obvious, but in the age of coronavirus, public health regulations are always evolving – and vary widely from country to country. tools like Airheart covid restrictions map are useful for planning, but it’s always best to go straight to the source. Check the U.S. Department of State Travel Advisory and your destination’s official government website before booking anything.

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

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

And don’t forget to check the 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 as Austria no longer accepts travelers from the Balkans.

Make the most of your time zone

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

If you need to be online during East Coast hours, trying to work from Bali (12 hours ahead) will likely wear you out. But you can get to Machu Picchu without ever leaving your time zone.

Work in the morning and explore the nightlife in the evening; or working at night and hiking in the morning – there are no right or wrong answers. The most important thing is to communicate with your team to make sure you’re all on the same page about when you’ll be online. I have found that setting these expectations early is very helpful, especially when issues arise.

Even if your job requires you to stay in the office for most of the day, you can still explore places close to your home base. When I was working from Medellín, Colombia, I was able to go paragliding on my lunch break because I found an excursion that would pick me up and get me home within the hour.

Home is not always where the WiFi is

Even if I want to work every day in a sunny café in Lisbon, sipping espresso and munching pasteis de nata, the reality is that working in public spaces has its drawbacks. And if you’ve ever tried to take a Zoom call in a crowded cafe, I’m sure you know them too.

Additionally, public WiFi networks – even those with passwords – still pose a significant security risk, so a private network or VPN is always recommended for digital nomads. When looking for Airbnbs for work, look for terms like “WiFi,” “connection,” or “remote work” in reviews to weed out stays with a spotty connection.

Sometimes, however, 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 bus full of people trudging through a mile of slush to reach the city – and a stable connection. On the other hand, the cafe where I worked that afternoon, Vertiente Café with ideaswas immensely comfortable.

Be strategic about your packaging

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

If you have already explored the A bag subreddit, you know there’s a whole subculture around minimalist travel. And while I appreciate their principles (“focus more on the experience than the logistics”), I opt for a slightly more moderate approach.

Embrace overpacking: the case against carry-on luggage

I use the Minaal Hand Luggage 3.0 as my main bag. It’s 35 litres, flattens into a crepe when not full and has all the pockets I could need. I pair this bag with a cheap multi-use backpack I picked up at the mall for $15. It’s easy to put it on the side or on the chest when I’m navigating through airports with both bags. Plus, its modest, cheap 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 a week and then do laundry as needed. This involves researching how to do laundry in every place I stay. In Argentina, for example, it is rare to find a self-service laundry, but lavender where you can have your clothes washed and ironed are on every corner.

Traveling alone doesn’t have to be lonely

No, unless you wish.

For me, traveling solo is an almost spiritual experience. There’s nothing quite like the feeling of wandering the back streets of a new city – soaking up all the details that make this place feel unlike home. I often curate urban wandering playlists for this very purpose, like this one of Czech folk musicians and composers that I did for Prague.

That’s not to say there aren’t days, or even weeks, when I feel lonely. When I start feeling this, I find the easiest way to replenish my extrovert tank is to attend fellow traveler gatherings. I’m almost always able to find meetups by searching for “digital nomad” or “expat” groups on Facebook or Try going on a language exchange to brush up on your skills or help someone else learn your native language.

But I also encourage you to embrace the unique freedom that solo travel brings. Go ahead and strike up a conversation with that person standing in line at the station. You never know where it may lead.

My friend Renan and I were complete strangers when we accidentally made eye contact at Medellín airport; five minutes later, we were exchanging stories about our hometowns (he’s from Brazil). Fifteen minutes later, his translation skills were helping me out of a vaccine check snafu at the airline office.

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

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

Peter Hershey was previously 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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