Digital Nomad Life—5 Years as a Digital Nomad

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This year has been different … way different. We’re in South Korea as we pass 1,825 days of living life out of a carry-on bag.

This is our fifth year of full-time travel. From the beginning, this journey has been filled with unexpected bumps in the road. Sometimes a flight is delayed. Maybe a taxi fails to pick us up. With some frequency, we’re served a dish we didn’t realize we’d ordered.

We had planned to be in Tirana, Albania today. That plan evaporated, along with any illusion of control, early in 2020.

Let’s back up for a second

My wife and I have been traveling for five years. We started our journey on our twenty-fifth wedding anniversary–June 23, 2015. We’ve visited more countries than I can count. We’ve met more people than I can remember. We’ve eaten more kinds of food than I even knew existed. And we’ve had more fun than we deserve. It has truly been amazing.

In our minds, our “year” runs from June to May. It’s bookended by a return trip to our old home, Raleigh, North Carolina. We drop back into the area to see family and friends, get our teeth cleaned, and get our annual physicals.

A quick review of the past twelve months

Back in May of 2019, after an enjoyable ten days of seeing family and friends, we headed off for a year in Latin America. We’ve figured out that this lifestyle is easier if we focus on a particular region rather than zigzagging all over the planet. Staying in one or two time zones, minimizing long flights, and using fewer languages helps us stay sane-ish.

Peru

We headed down to Peru and ate and ate at some of the world’s best restaurants in Lima and Cusco. We also managed to make our way to the tops of two peaks at Machu Picchu, and enjoyed quite a few weeks just soaking up the Andes scenery.

Bolivia

After nearly two months in Peru, we flew over to Bolivia to see the salt flats and La Paz. Late July is midwinter in Bolivia; we were freezing, and when the snow started falling, that seemed like a good reason to wrap it up and fly away.

Ecuador

We zipped over to Ecuador to see Quito. Then we spent some time on a yacht in the Galápagos Islands, followed by a month in a very tiny Pacific coast town called Puerto Lopez, where we did some whale watching. Ecuador exceeded our expectations on the nature front.

Panama

The continuing chilly weather drove us north to Panama after 7 weeks in Ecuador. The highlight of Panama City was the canal. We were oddly fascinated, and spent a couple of days exploring the locks at both ends and watching ships pass through. Then we flew over to Boquete to enjoy the mountains, followed by a week on a sailboat we chartered in the San Blas Islands, which were both beautiful and warm.

Chile

Once we had thoroughly thawed out in Panama we flew back south to Santiago, Chile, where the air was cooler but the politics were hotter. We had a chance to see the ongoing political protests from a safe distance.

Then we flew down to a small town–Punta Arenas–which was much calmer, until a small group of protesters torched the building immediately next door to our hotel. A massive fire ensued, accompanied by soldiers with water cannons and tear gas. It was quite a show. We quickly headed down to Patagonia where the scenery was calmer and beyond amazing.

Argentina

After three dramatic weeks in Chile, we crossed the border to Argentina where we spent nearly two months. In El Calafate we visited glaciers, in Bariloche we drank beer and hiked in the mountains, and in Buenos Aires we enjoyed the sights, a holiday visit from family, and the beef.

Brazil

Iguazu Falls drew us briefly to Brazil where we stayed inside the national park and woke up each morning to a waterfall that was unlike anything we’d ever seen. Amazing.

Uruguay

Sometimes we need to get some work done. Too many great tourist attractions make it hard to be productive. A month in Montevideo, the capital of Uruguay, proved to be the perfect spot to catch up on work. The city is modern, functional, and convenient. We found great food, nice people, and beautiful waterfront walkways for getting some exercise. A couple of weekend drives gave us a greater appreciation for everything Uruguay has to offer.

Nicaragua, El Salvador, Guatemala

Then we went full tourist and jumped into Central America with both feet. It’s hard to get work done when we’re moving quickly, so we abandoned work mode and embraced holiday thinking. Two weeks on Little Corn Island in Nicaragua, followed by a Pacific beach in El Salvador, and then a quick visit to the Tikal ruins in Guatemala made for a great vacation. There were definitely some pina coladas involved.

Mexico: The wheels started to come off

We arrived in Puebla, Mexico for a week of eating. We’d long wanted to visit the city, and we loved all of the Mexican food we consumed. But at that point (early March), the virus was clearly becoming a thing. Temperature checks in most Central American airports alerted us to what was coming as we arrived in Mexico. Tension was in the air.

Then, just as we checked in at a Hilton Resort in Playa del Carmen, the US announced a travel ban.

The resort was going strong when we arrived but quickly became eerily quiet and a little weird. We’d booked this place because we’d found an amazing deal months earlier. As guests headed for the exits, the pool crew continued to play loud dance music and conduct bikini contests–it was surreal. Social distancing was now a thing, and it was easy at the gigantic, empty resort, but it was uncomfortably bizarre.

The plan, after that week at the resort, was to spend March in Mexico City in an apartment. We were scheduled to leave the resort early Sunday morning. We figured we’d just hole up in the apartment away from other people, but we weren’t so sure about Mexico City.

Our research told us to ride the virus out in a place with hospital beds. The best information said go where there’s solid infrastructure. Mexico City was quickly out.

Tokyo had very few Covid-19 deaths, a huge number of hospital and Intensive Care beds, and was still open to us, as Americans entering from Mexico. We’d considered Hong Kong, Taiwan, and Singapore. They were either closed or closing.

We made the decision at 9:30 PM on Saturday night, and booked a flight to Tokyo. Six hours later we were in the air, bound for Japan on a mostly empty plane. We spent a very long night worrying every time someone coughed.

We headed to infrastructure

After five weeks in Tokyo, still with only a couple of hundred deaths, Japan declared an official state of emergency. Business slowed down fast. The streets got emptier as shops and restaurants closed. Everyone was inside their homes. We were inside our Airbnb. It was clear that Japan was going to shut down tight for at least a while.

Should we stay? Should we go? There were no good answers, and the variables had grown exponentially. We spent a week debating our options.

A quick flight out

And that brings us to Seoul. We jumped on a short flight over to Seoul. The drive to Narita Airport, just outside of Tokyo was fast, with zero traffic. The huge airport was empty–silent. It was disconcerting.

Our flight was mostly empty. We landed in Seoul just two hours after takeoff. Police and soldiers processed us and escorted us to a private bus, and an hour later we were sealed up in a dorm room on a government campus, two hours south of the airport. The fully hazmat-suited quarantine center workers who showed us to our room were the last humans we saw for the two weeks of our mandatory quarantine. Even the three meals that were delivered each day were left by the door for us to retrieve, with zero contact.

So many folks we know have struggled with working from home. We’ve been working from “home” for years. We’re fully functional with a laptop, a mobile phone, and earbuds–no adjustment required.

We’re oddly well suited for the confines of quarantine. When South Korea confined us to that 11 x 11-foot room, we were fine. In fact, that room was bigger than some we’ve had along the way. The constant disinfection of the hallway beyond our door just made us feel more secure (we’ve been in plenty of hotels that could’ve used a bit more disinfection!).

Then, after two weeks, we were released in Seoul.

Freedom. But still, a slightly weird version of freedom. There is very little community transmission in Korea, but our awareness of the virus hasn’t simply disappeared, even in the relative safety of Seoul. We’re still on alert, at some level; the virus is always there, in the back of your mind. Touching a doorknob still doesn’t feel the way it used to feel. I’m guessing you know exactly what I mean.

Going forward

We’ve been pretty flexible for a long time, living as we do. But this virus is requiring flexibility on an entirely new level.

There are safety issues, of course. But there are also moral issues, border issues, quarantines, airline issues, complexities involving transit airports in countries that are prohibiting passage, countless forms, temperature checks, and more. Living this lifestyle just got much more difficult.

As the environment changes, everything is trickier. I’m reminded of the lessons I was taught when getting my pilot’s license. The instructor explained the danger of flying into a blind canyon. If you’re not careful, the plane ends up in pieces on the canyon floor when you discover there’s not sufficient distance to climb over the canyon wall.

It’s easy right now to end up in a country where one can’t legally stay, but from which one can’t easily travel to a place they’d like to go. We could inadvertently end up in a place we don’t want to be, and which leaves us with options we’d rather not choose.

We’re free from our most recent quarantine, but we’re not really free. I suppose this is how it feels to be from most countries in the world where passports aren’t so powerful and money is often tight. It’s good to be reminded of all we take for granted. But I have to admit–it’s an uncomfortable lesson.

Grieving our loss

Looking back on the year, it’s sad how much of it seems like a faint and distant memory, now overshadowed by the virus. So many people, places, meals, and experiences are buried by the crisis taking over our memories. It’ll be interesting to see how it all looks a few years from now when we can see it with some perspective.

Right now it just feels like loss. Some of it is trivial–like how hard it is to see when the mask makes my glasses fog up. Some of it is overwhelming, when we’ve experienced the loss of someone to whom we have a strong connection. It’s difficult to see a silver lining right now.

Going home

So many folks we know are hanging out at home. We have no home. We’re used to that idea, and it has always been a little weird. But it’s definitely weirder right now. We’ve watched as hotels have closed, airlines have shut down, borders have been sealed–it’s an environment that makes one very conscious of the desire to have a secure nest, somewhere in the world.

Some have suggested that we go back to the United States. We might. That might prove to be our only option at some point. But at this stage, it’s a bit challenging to know exactly where home might be. We’re not quite sure where we belong.

People are on their best behavior

I’m sure the loss of control we’re all feeling triggers panic in many. Panic doesn’t always turn out well. People do crazy things when they’re frightened. They get angry. They behave badly.

But that’s not what we’ve observed.

We’re feeling like people around the world are kinder, gentler, more welcoming and open.

Our experience has been one of people reaching across boundaries to help. The quarantine team in South Korea scooped Lisa up when she stumbled. The soldiers at the airport were all kindness. They kept us informed as we were processed, and even though we couldn’t see their smiles, we could see welcoming eyes behind their protective shields. The people helping us in stores, restaurants, taxis, and airports have all been more human than usual. It’s nice to see people, even behind masks, coming together, rather than letting this crisis push us apart.

So what’s next? Where do we go? What do we do now?

We don’t know. Control was always an illusion. Covid-19 just helped us see that a little more clearly.

Prior Years: Below are my updates for 2016, 2017, 2018, and 2019.


2019–4 Years as a Digital Nomad Lawyer

“What causes you the most stress?” a friend asked.

It’s an insightful question, asked by a lawyer friend we met up with in Tokyo.

Mostly we get the same questions over and over: What are your favorite places? What’s in your luggage? How do you pick destinations? We’re always happy to answer, but we rarely have to think about what we’re going to say because we give the same responses so often.

The stress question, though–that one stopped us cold. We had to think about the answer.

Only one thing truly stresses us out

The answer, when it popped into my brain, surprised me. But I had it right. When I heard the response come out of my mouth, I knew it was real. I’d actually found the most stressful piece of our lives.

I have to admit that it’s trivial. The reality is that our nomadic lifestyle isn’t particularly stressful. It’s easy compared to our old life in the suburbs, where the air conditioner had to be replaced, the kitchen cabinets were falling apart, and the teenagers might get arrested. Just taking the cat to the veterinarian could trigger a twitch in my left eye as I anticipated the coming invoice. Suburban life requires mad coping skills.

It’s seemingly trivial but it’s actually stressful

Stress is, I suppose, part of life. And if one’s life isn’t particularly stressful, then even the most trivial stressor can generate a negative reaction. I have to confess that I’m slightly embarrassed to admit that this is the most stressful thing happening to us as we keep moving. But here we go:

The biggest source of stress for us at this point is having to show up on time. That’s it. Being punctual is stressful when you don’t have much else creating stress.

I apologize for complaining. But that friend asked, so we answered. And now, for your reading pleasure, I’m going to justify my stress, even if it is objectively trivial.

Being on time is easy for you. It’s hard for me. Seriously.

Being somewhere, at a prescribed hour, is simple when you know the way. It’s straightforward to estimate the time required to get there, park, walk, whatever. You’ve been there, done that, and have a pretty reliable sense of how things work in your area. You move about with ease.

Lost without a clue

But for us, getting nearly anywhere is a new experience. We’ve never been there before, we’re likely to encounter the unexpected, the transit system probably won’t work the way the last one worked, and it’s usually organized in a language we don’t understand.

We’re on an obstacle course and it’s very challenging to predict the specific time at which we’ll cross the finish line.

Of course, technology helps. I can’t even imagine having to do what we do without Google Maps. It saves us nearly every day in one way or another. It’s amazing that we can show up in almost any city and find our way to a hipster coffee shop with a single click. Truly amazing.

But when we’re hunting for coffee and it’s just the two of us, we can arrive when we arrive. There’s no pressure. The only constraint is getting our caffeine fix before it’s so late in the day that we’ll have trouble sleeping that night.

Throw in other people and the stress level rises

When we’ve agreed to meet someone, like our friends in Tokyo, we’ve got a deadline. These appointments are pretty much the only hard deadlines we face. These small events get loaded up with all of the stress we’ve got.

We felt it in Tokyo. We feel it when we’ve got to get to the airport or train station to move on to the next stop (we go really, really early). We felt it when we flew to Berlin to get vaccines at a clinic. Even a restaurant reservation causes a little tension. We’re never quite sure if we’re going to make it on time, and if we’re late, we might have to negotiate in the local language to get ourselves squeezed back into the schedule.

But let’s get real … who cares?

Yeah, that’s our big source of stress at the moment. And realistically, we don’t bump into the issue very often because we don’t have that many meetings. It’s pretty rare for us to have a deadline involving logistical challenges.

Thankfully, we do get to meet friends as we travel. We’ve met quite a few other nomads in the last few years, so we often cross paths with those folks. Sometimes one of our old friends or colleagues from the U.S. happens to show up where we are, and that’s always a real treat for us. A few times a year we get to spend time with friends and family who decide to come to meet us in a particularly interesting destination. We love all of the opportunities we get to connect with people. It’s pretty awesome.

So we’re not complaining about the mild stress of a time commitment. We’re happy to have the chance to get lost, be late, and catch up with the people we get to see. Any stress we feel as the blue dot on the map spins in circles pales in comparison to the joy we get from meeting up with friends, or getting on a plane to explore a new country.

Update on our movements

My last nomad update was written a year ago in Montenegro. Since then we’ve been to Latvia, Lithuania, Norway, Russia, Italy, Lebanon, UAE, Oman, Ethiopia, South Africa, Namibia, Senegal, The Gambia, Morocco, Portugal, and Spain.

Latvia was probably the most eventful stop. We got a speeding ticket, plus we got to ride in an ambulance and Lisa spent the night in a hospital. She’s fine.

We loved the food in Latvia (although not at the hospital), as well as in Russia, Lebanon, Ethiopia, Morocco, and Spain.

We loved the scenery in Norway, Lithuania, Italy, South Africa, and Namibia.

We loved the people in Ethiopia.

The other places are more complicated. It’s not easy to label our impressions of each destination. But each place we visit is a place we’ll never forget.

Now we’re in Peru, where the mountains near Machu Picchu are so beautiful that it feels like I’m cheating when I take a picture. It’s just too easy–iPhone photos shouldn’t be this stunning.

One big change over the past year

If you skim the list of places we’ve been over the course of the past year, you’ll find that we moved quite a bit from as far north as Russia to as far south as South Africa. Even so, we barely changed time zones.

Sure, we moved backward or forward by an hour from time to time, but mostly we stayed in the same general time zone. That made adjusting to traveling easier.

This year (and we think of our years as June to June with a visit back to Raleigh to see family and doctors at the end of May) we’ll stay in South and Central America. Again, we’ll stick to a tight range of time zones.

I’m not quite sure how we happened upon this approach (which likely means Lisa thought of it) but it impacts us in ways other than avoiding jet lag. With shorter trips from one location to the next, we’re able to fly during the daytime, which is easier, and we’re able to book shorter flights. Those shorter flights tend to be less expensive and easier on our creaky bodies. This system has been a big improvement.

I’ve got to stop calling myself a lawyer

These updates started off as year one, year two, etc. as a digital nomad lawyer. But then, I sold my law firm. Now I’m not practicing law, and I’m handling the work here at Rosen Institute full time.

I’m finding it a little difficult to stop calling myself a lawyer. But, it’s time. I guess I’ll change the headline for the fifth year of my nomad reports. Letting go is tough. Being a lawyer is way more, for most of us, than just an occupation. It’s an identity. It’s how we think of ourselves.

Being a lawyer, while traveling the world, worked well for the first three years. The law firm more than supported me and my family. There’s zero reason to think that you can’t make practicing law as a nomad work out for you, if that’s your vision for your life. It’s not nearly as challenging as you might think. I did it. You can too.

But now, I’ve moved on from the day-to-day practice of law. I had a great run. Now, I’m loving this new work and it’s even easier to do while traveling. Yep, it’s time to switch up the identity.

Acceptance of the challenges

There are things–normal things–which become a challenge, depending on where we’re living at the moment. Buying dental floss is rarely easy. Lunch can quickly turn into a comedy, as things I didn’t realize I’d ordered show up at the table. You’d be surprised how often housekeepers open the door as I stand there naked, getting dressed. I know they’re certainly surprised.

But this is just the way we live now. We don’t even think about the fact that we have to use Google Translate on five different toothpaste boxes before making a selection.

There’s an acceptance now; we’ve (mostly) stopped resisting the challenges. I accept that communication is awkward and sometimes difficult. I accept that there won’t always be a power outlet where I’d like. I accept that certain things, like negotiating taxi fares, are an annoying part of my life.

It’s different than living in the suburbs of Raleigh, North Carolina. But it’s what we do, it’s how we live, it’s the choice we’ve made. We love it. If we didn’t, we’d stop.

When will we stop traveling?

We’ve made friends in places I couldn’t have picked out on a map back on the twenty-third day of June in 2015 when we started this life. Even if it’s just a “like” on Facebook, it’s still pretty cool for me to know I have a connection with people around the globe.

The longer we live this life, the more I realize that there are few strangers. There are just many (many!) people we haven’t yet met. We’re always open to meeting someone new. That’s something I didn’t anticipate enjoying quite so much when we set out four years ago.

Of course, in addition to making friends along the way, we love meeting up with old friends as we go. If we’re crossing paths with you, we’d love to get together.

We’ve been on the road for four years now. At this point, this lifestyle is our life. It’s normal for us. When we pass through an airport we’ve been through before, it feels a bit like coming home. It’s just the way we live now, which sounds like it should be weird, but it feels entirely normal. It’s hard to imagine living in one spot. We’re having way too much fun.

I’m pretty sure, assuming our health holds up, that we’ll be living this life when I report in again in June of 2020. There’s no reason for us to stop, and there’s every reason to keep moving forward. We’ll continue exploring the world until something changes. For now, we’ll just keep moving on.


2018–3 Years as a Digital Nomad Lawyer

Sold the house, gave away the stuff, packed a carry-on bag and set off to see the … yada, yada, yada.

You’ve heard the digital nomad story from me and others, and most folks now have some hooks for understanding the lifestyle. We’re three years in and this is my annual update. You can catch up at year one or year two. You can even see us in the digital nomad documentary One Way Ticket.

Feeling at home

At some point in the past year (I have no idea when it happened) I started feeling at home anywhere in the world.

It’s odd, because I’m not generally someone who’s comfortable anywhere. To find myself comfortable everywhere was totally unexpected.

It snuck up on me. I was just sitting in a coffee shop one day, expecting to feel like I always feel–a bit out of my element–and it struck me that I felt like I belonged. It happened in all sorts of places. It happened when I least expected it.

I’m in Luang Prabang, Laos and I feel at home sharing the table with a Chinese couple with whom I share no language. He’s slurping his eggs up with his face down near the plate. I’m eating my toast with jam. He’s drinking tea, I’m drinking coffee. We all smile and nod, not saying a word, and I’m perfectly content.

I’m in Dahab, Egypt and feel at home slapping high fives with the dozen tiny children who follow me for a block each night as I wander back from dinner.

I’m sitting outside, which is actually inside the home of a family in Ubud, Indonesia. We’re sharing a dinner of rice and fish and vegetables. The children and the grandparents can only communicate with me and Lisa with gestures. The husband has great English and his wife has some. I feel at home, even as Lisa inadvertently sits on the mat which turns out to be the dinner table.

I feel at home when the couple across from us stares so hard that I can feel their eyes on my skin. It’s not the first time, it happens frequently, and I’ve grown accustomed to being the subject of curiosity. We smile and nod and we say goodbye to the staring couple when we leave.

I feel at home when the waitress shakes her head “no, no” after I randomly pick something off the menu, since I have no idea what the Korean menu actually says. She points and gesticulates me into a different order and I have a great meal, thanks to her concern.

I feel especially at home on the 19th day of buying a croissant from the same Croatian woman at 7 AM each morning when she finally lets her stern demeanor down and, for the very first time, smiles like she remembers me.

I feel at home when I stumble and fall on the street in Mumbai, cutting my face as my glasses smash into the concrete, and Indian men rush over, scoop me up, dust me off, and help me get moving again toward my hotel.

I feel at home as the young woman stops to help us buy subway tickets and explains the machine. I feel at home as the young man stops to translate the “closed for remodeling sign” on the restaurant door and then walks us three blocks to a place he likes that definitely has something vegetarian for my wife.

I feel at home when the Vietnamese soldier with the big machine gun waves at me to move back, to go the other way, and gives me a forceful look.

I feel at home confronting the Turkish taxi driver who’s ripping us off and who concedes and gives us back our money. I feel at home assaulting the other tourists with conversation in the rooftop bar, when they thought they were going to have a quiet drink at the manager’s happy hour.

I feel at home talking to anyone and posing for pictures with locals, other tourists, and hotel staff who want a record of our time together. We always make sure to get a picture on our camera too.

Feeling at home in the world wasn’t something I expected. It wasn’t something I aspired to feel. I didn’t know it was a thing. It just happened, and it’s wonderful. I’m still surprised when I realize that I feel like I belong, in a place where I clearly don’t belong.

It took a long time, I had no idea it was coming, I’m not sure I’ll feel this way in the next place we go, and I’m not sure I’ll feel this way forever. But for now, I feel at home wherever I am: anywhere in the world.

The stress is way down

Living this lifestyle did, for a long time, create some stress.

Early on, Lisa and I came to an informal agreement to keep our conversation to a minimum on travel days. That was especially important during our packing and departure. We knew that the less we talked, the less chance there was of an argument.

Recently, though, we’re talking more on travel days, because neither of us is nearly as stressed as we once were during transitions. I think we both realize that things will work out, even if there are unexpected glitches.

The airport in Yangon, Myanmar turned the stress tide. Before that flight from Yangon to Bagan, we always assumed the biggest problems would be of our making. We used to worry about arriving late, going to the wrong terminal, or failing to print our boarding pass.

When we arrived at the airport in Yangon we couldn’t find the airline desk for the airline that had sold us our tickets.

In fact, the airline named on the boarding pass, which we had printed out, just to be on the safe side, did not exist. No one had heard of the airline. It wasn’t in the airport because it wasn’t an actual airline.

What happened? Everyone agreed that our airline was not an actual airline. One of the other airlines gave us new boarding passes for their flight and we got on the plane about an hour later than we had originally expected to depart. How much did it cost? Nothing. They just took us without issue.

These sorts of things have happened regularly. One airline insisted that we present the credit card we had used to buy the tickets, which I had canceled and thrown away in the interim. The supervisor put us on the plane anyway, without the card. On many occasions we’ve been late for connecting flights–the airlines nearly always make sure we make the connection.

If all the travel fears we used to have actually turned into reality, the airports would be filled with stranded passengers every night. They’re not. Things work out, most of the time, for nearly everyone.

It took us a while, but we’ve stopped worrying about travel. We have always ended up getting where we’re going, finding the hotel or apartment, getting the visa issue fixed, finding someone to help us get the SIM card, or finding a different taxi to take us where we actually needed to go.

It’s so freaking easy that it’s embarrassing sometimes

We live somewhere new every few weeks, sometimes even every few days. We work remotely. We stay in hotels and Airbnbs. It’s not rocket science. It’s not hard. It’s not more expensive than living in your average American ‘burb.

To be honest, being a digital nomad is ridiculously easy. A monkey could do it–a monkey with a carry-on. We constantly have people tell us how amazing it is that we’ve figured out how to do what we’re doing.

We love the attention and the flattery, but seriously–this is easy, embarrassingly easy.

I get up many mornings and head to the hotel breakfast room to eat my included breakfast. The fruit has been sliced for me, usually there’s an omelet station, and I don’t have to wash the dishes. Then I find somewhere to work–a coffee shop or coworking space–and someone comes in and cleans our hotel room while we’re out.

We Uber to a late lunch in a nice restaurant and then go for a walk or do a tourist thing like a museum or a park.

This is easy, easy, easy. We don’t deserve any credit or praise for what we’re doing.

If this lifestyle is of interest to you, then don’t be put off by imagining it as challenging. The tough decisions I used to make–like which HVAC system to buy when our $7,000 unit broke or how to pay for new kitchen cabinets and countertops–have been replaced by decisions like whether we’d prefer the beach in Sri Lanka over the one in Mozambique.

Our lifestyle isn’t for everyone

I used to think this lifestyle made sense for everyone. It took me a while to get out of my own head and into the heads of others on this topic. Obviously, lots of people wouldn’t like living the way we live.

We both happen to have a high need for novelty, as well as tolerance for uncertainty. We cope well with minimal connection to the people surrounding us. Sometimes we form relationships with the people we meet, but sometimes that doesn’t happen. It’s just the two of us.

Our personalities make this lifestyle work for us. Others would find it unsettling, disruptive, and disconcerting. It’s a vacation from which one never goes home. For many folks, the going-home part is one of the best parts. I used to love getting home after a trip and I remember that feeling well. What we do now feels very different.

We lose some things by traveling so much. We don’t see our family as often as we’d like. We don’t have the same community connection as we did in the past. We aren’t able to rely on routine to refine the easy way to get things done. Yep, we miss out on some stuff, but we’re not complaining. We could settle back into a home in an instant if we made that choice. This lifestyle fits our psychology. It works for us, but it truly isn’t the right choice for many others. Life is pluses and minuses, no matter which path you follow.

What’s happened since my last update?

We spent last summer in Europe. We visited Hungary, Poland, Croatia, and Georgia.

Then the temperature started to drop in Europe so we headed to Asia.

We spent time in India, Sri Lanka, Thailand, Indonesia, Malaysia, South Korea, Japan, and China and flew to the US in early May for three weeks, for a visit with family, a little business, and many medical checkups.

Now we’re back in Europe. We just wrapped up a month in Montenegro and today we’re flying to Riga, Latvia.

As we move along and pass through places, life keeps happening. Three things have marked this year for us in addition to the destinations–one business, one family, one health.

Our business: If you’re a regular reader then you know that I sold the law firm back in October. That was a huge event for me. I’d been running the law firm remotely for a decade. I didn’t sell the firm as a result of our traveling schedule, but it sure does make the time zones easier when I don’t have to return calls. The travel had zero impact on the firm, but running a law firm, as you know, is stressful. Having that behind me is awesome.

Our family: One of our kids is a rising senior in college, having transferred schools last summer. We’re now counting down the days to graduation. This third year of living nomadically has involved lots of discussion about the kid’s adjustment to the new school and, now, the final steps toward graduation. Thankfully, it has all gone well, but it has also involved many moving parts and transitions. It feels a little odd to sit down to lunch on a pier in Baosici, Montenegro and chat about the kid’s question about getting new tires on the car, but that’s what has to happen when one lives the way we’re living.

Our health: We both gained weight for the first two years of traveling. That’s not something I can afford to do with my history of heart disease. I’ve got to maintain my weight in order to stay alive. Our habit of eating in restaurants doesn’t make that easy, but it’s hard to do otherwise in each new place.

About a year ago I stopped eating dinner. I shifted from three meals per day to two. It worked. I dropped weight steadily from the first week and have continued to trend down without gaining any of the weight back. Apparently eating less causes one to weigh less–who knew?

After about a month Lisa joined me on this new plan and it worked for her as well. There is, of course, the endless debate about the right way to maintain weight. I’m no expert, but eating less is working for us so we’ll keep doing it. We don’t want to have to start purchasing extra seats for ourselves every time we fly.

What’s next?

Now that we’ve gained some understanding of the flow of a year of travel, we’ve been planning loosely in one-year increments. We’re book-ending our years with a visit to Raleigh each May to see family, friends, and doctors.

We have the entirety of the coming year broadly planned and are slowly acquiring plane tickets as we have the option to use our accumulated points. We’re usually able to find the best free business-class seats if we book eleven months in advance.

The coming year includes Latvia, where we arrive today. Then we’ll visit Lithuania, Norway, Moscow and Saint Petersburg in Russia, and then we’ll fly to Italy and spend time in Rome and Sicily.

We leave Europe in October to visit Beirut, Dubai, and Salalah, Oman before heading down to Ethiopia.

We’ll spend the rest of our year in Africa visiting South Africa, Namibia, Senegal, and Morocco before heading back to the US for a couple of weeks in May. Hopefully, we’ll be attending a graduation while we’re in America.

What else is next? It’s hard to say, as predicting the larger pattern when living this way is difficult. It’s rarely the broad strokes I remember, anyway. It’s the little things that stick in my mind and change me as we move through the world.

I’ll never forget walking silently along the path in Auschwitz with a group of tourists. No one was speaking as we all took it in. The only sound was the soft crunching of our shoes on the gravel as we walked toward the incinerators. Then a train whistle sounded in the distance. It was eerily unforgettable.

I’ll never forget the crumpled, legless man sliding along the pavement in the train station in India, using his hands to propel himself slowly. He reached out and touched my leg as I bought myself a drink. I pulled away reflexively. I’m still uncertain how to process that memory.

I’ll never forget the music flowing up from the courtyard below our apartment in Tbilisi as the Georgian men harmonized their polyphonic singing, a cappella. It felt as if the sound drifted through our window like smoke. It lifted us up as we peered down through the glass, listening as they sang late into the night.

We’ll have to wait and see what’s next. Something unexpected will happen and we’ll be ready to take it on, take it in, and enjoy it when it comes. Year four is underway and we’re all in.


2017 – 2 Years as a Digital Nomad Lawyer

The nest was empty. Our second child had graduated from high school three days earlier. The apartment was cleaned out. We were ready to hit the road for parts unknown.

We had no plan to return.

This was the beginning of our digital nomad life. It was our 25th wedding anniversary.

We had traveled quite a bit in our lives, but June 23, 2015 marked a new beginning.

We trimmed our belongings down to what would fit into carry-on bags. There would be no coming home this time, because we no longer had a home to come to. We untethered ourselves from any place in the world. Honestly, it felt a little weird.

Two years later, that weirdness has passed. We’ve grown accustomed to being untethered. We drift often, and we like it.

Sometimes, on travel days, when we’re between two places and literally homeless, we get a feeling of weightlessness. Our few possessions are with us. We haven’t found a place to sleep yet. We’re in space. That’s when we feel the most disconnected from the world. That feeling has become comfortable now.

Over the course of the past year, we’ve spent time in Ireland and Scotland. I went to America to conduct some workshops while Lisa took our younger kid to France. We reunited in Thailand and then spent months in Myanmar, Laos, Malaysia, Singapore, and Vietnam.

When the weather heated up in Southeast Asia, we headed to Jordan and then up to Lithuania, Belarus, and Hungary. We’re in Budapest now.

I won’t re-report on my first year. Go back and catch up if you’re new. Today, I’ll plunge forward and clue you in on my life over the past year.

On this second anniversary, I’d like to share some observations. They aren’t particularly well connected to one another. They’re just the things I’ve noticed as we have moved through time and place.

It’s Not About the Stuff

Before we initially left home, I was obsessed with the material goods of travel. I read blogs, reviewed products, and ordered lots of stuff from Amazon.

I did a lot of thinking about traveling, but all that thought turned out to have little to do with actually traveling. Thinking and doing are not the same.

During the years before we left, we spent a lot of time planning. I used much of that time to identify problems and buy solutions. I like buying stuff, so this method of planning was perfect for me.

I bought travel clothes from TravelSmith. I wanted to be sure I had the right pants and underwear for quick washing in the sink, for escaping bandits, or whatever.

I bought SCOTTeVEST jackets with dozens of pockets so I could store my gadgets, sunglasses, and hats.

Since I would only own one pair of shoes, I tested countless styles to find the one that would work in every setting.

I experimented with backpacks in a quest to find one with the perfect ratio of features to weight without sacrificing style.

None of that made any difference. My preparation was pointless. I no longer own anything from TravelSmith. I got rid of the stuff I put in the SCOTTeVEST pockets and then jettisoned the jacket.

I wear whatever sneakers I can buy in my size when my old pair wears out. (I just move quickly through the fancy restaurants and put my feet under the table before anyone notices.)

I ditched the backpack and bought a rolling bag after watching my wife traverse airports without sweating.

What I’ve learned is that my stuff isn’t important. The stuff doesn’t make a difference. I assumed it would matter, but once I left, I realized that specific jackets or shoes or underwear just aren’t the key to anything.

Planning and thinking about all that stuff before I left was a good way to enjoy anticipation. Anticipation is awesome, but my wife and I are beyond that. I’m in the middle of my adventure, so I don’t need any tricks to help me enjoy it.

When you’re traveling full time, you do think about stuff, but in a practical way. For instance, when we were in Ireland, I needed waterproof shoes. I didn’t think about it. I walked into a store, bought the first pair that fit, and asked the salesperson to dispose of my old shoes. Done. I walked in wet, walked out dry, and the adventure continued.

I Learned Every Foreign Language

We were having lunch in a restaurant in Mexico when our companion taught me something seemingly trivial that changed everything.

We had been seated and were considering the menu. The waitress approached and said something in Spanish.

I panicked.

“What did she say?” I asked my well-traveled, Spanish-speaking companion.

He looked at me and responded with a question: “What do you think she said?”

I was blank. I had no idea what she had said. I didn’t speak Spanish.

Our friend explained that the waitress had asked for our order. He walked me through the situation, and we examined it carefully. Without the stress of a foreign language coming at me, I was able to see the encounter more clearly.

We had been seated and handed menus. We had studied the menus and put them down. The waitress came to take our order. She was doing exactly what servers do. It’s a ritual. It gets repeated at restaurants all over the world countless times per day.

The context revealed everything once I stopped being stressed by the barrage of Spanish. She wanted to take my order. If she had said it in English, I wouldn’t have even heard it or paid attention. I’d have understood her request without even listening, thanks to the context and familiarity.

My anxiety about my lack of language skills created communication barriers. As I worried less, I understood more. It’s like magic.

Now, when I approach the bakery counter and the guy asks what I want in Greek (I guess that’s what he asked; he could have told me that my fly is down), I just point, and he serves the delicious pastry.

When I need to pee, I stand up in the restaurant and look around quizzically, and the server points me toward the restroom. When I want to pay the bill, I gesture and she takes my credit card. She says “thank you,” I assume.

Language barriers are diminished substantially once we relax. Context gives us plenty of information in most cases. Google Translate takes care of the rest (more or less).

I said it was trivial, right? It really is trivial. But for me, it changed everything. It allowed me to relax. This realization reduced my stress level dramatically.

Yet I Barely Communicate

Understanding context and relaxing has helped tremendously, but the language barrier I experience as I travel remains frustrating.

Language isn’t a problem in most respects. Over the past two years, I’ve mastered the art of wordlessly ordering food and buying deodorant, toothpaste, and dental floss. We can even get our laundry done with only a few words.

(Interestingly, I think we spend more time figuring out laundry than we spend deciding where to go next. I hadn’t ever considered how much time the 7 billion people on this planet spend on laundry. It’s considerable.)

But the language barrier is a problem when it comes to relationships with new people. Lack of a common language makes it harder for us to get to know most of the people we meet.

We’ve created amazing connections with people who speak English. These relationships are intense, powerful, and sometimes shockingly deep. Our lifestyle results in a different kind of relationship than we experienced in our old, static lifestyle. It’s not better or worse; it’s just different.

We’re staying in touch with folks in Italy, Ireland, Malaysia, England, Vietnam, Mexico, Germany, Thailand, and other countries. But all of these people speak English. We aren’t able to get to know people who speak other languages.

Sure, Lisa speaks a little French, and she’s good with words in other languages. But realistically, neither of us can have a real conversation in anything other than English.

It’s sad because we have such amazing experiences with other English speakers. We realize what we’re missing with non-English speakers. We’ve come to understand how little we understand about them, their lives, their perspectives, and their feelings.

The more we travel, the more we realize how little we know. We’d love to learn more, but it’s difficult.

Of course, we could watch an episode of Anthony Bourdain and learn something about a place. But real learning—the life of the people, their dreams, their wishes for their children, their hopes for how their politicians will behave, their feelings about their neighbors, the special places they want to take us, and the insider tips on local food—all come from conversation.

We’re extremely happy when we get a chance to know people in a new place. It’s like going from watching a movie on an iPhone to seeing it in IMAX. Building relationships changes everything.

It’s incredibly sad to know now how much we’re missing because we can’t speak their language and they can’t speak ours.

The relationships we build with English speakers are sometimes so powerful and overwhelming that tears well up in my eyes when we leave. It’s often hard to leave our new friends behind.

Sometimes There Is Sadness

The connections we build with people and places can be so strong that it’s hard to say goodbye. The feelings sometimes make it hard to continue our nomadic lifestyle. We often miss people before we’ve left. We’ve become experienced at missing new friends.

Before it happens, we know how it’ll feel when we go. Anticipating our final day is hard when it happens nearly every month.

We don’t talk much on transition days. The hard deadline of a takeoff time creates stress. We move through the routine silently so as to avoid any disagreement. We’ve learned the hard way that we’re better off doing what needs to be done without discussing it. We can talk once we’re on the plane.

In the first year, the stress of transition was about logistics. Getting through packing, traveling to the airport, and boarding the plane usually presented some unexpected challenges. That’s not the situation now. We’re pretty good at navigating each step of the way without angst.

Our silence today is different. It’s less about stress and more about loss. We grieve for the loss of the relationships and the familiarity of the place. Sure, it’s balanced by the excitement of what’s coming, but the sense of loss hangs over us. It’s like the last day of high school or the end of summer camp. There’s a wistfulness that fills the air around us.

The people we get to know take on a larger-than-life role. They become the representatives of their country for us. They embody all of the people of that place. They are the country. Oddly, and somewhat frighteningly, we become our country for them. We are a larger, more real American presence than any anonymous ambassador they’ll never meet. We speak on behalf of our people for them in the same way they do for us. It adds to the powerful nature of our conversations.

Our conversations with people vary widely from the deeply personal to stiltedly diplomatic where every word is important.

We’re proud enough of our nation that we hesitate to express our own opinion without adding the opinions of our fellow Americans. It’s a balance we impose on ourselves because we see the people across the table trying to understand all Americans by listening to just us.

The conversations and the relationships formed through them are an increasingly important part of why we continue to live this way. It didn’t start out this way, but that’s been a big part of this second year.

No Plans to Stop

We get lots of questions whenever we meet new people. I get many questions from other lawyers contemplating this lifestyle. One of the frequent questions is “When will you stop?”

We have no plans to stop. We love what we’re doing. If anything, we’re more excited about our lifestyle than we were before the transition. Our comfort level has increased along with our competence and confidence. The momentum propelling us forward gets ever stronger.

Many people ask us about our favorite places. Truth be told, we haven’t been anywhere we didn’t enjoy. Traveling full time is different from being on vacation. Short holidays require prioritizing and ranking activities. We all want to use our time wisely when it’s limited. Traveling without end and actually living in these places lets us enjoy destinations others might not experience over a quick holiday.

But we’ve had special experiences in certain places. Interestingly, they’re not always the places you would expect.

We’ve visited some of these special places because of advice we received along the way. These spots aren’t places we’d have gone otherwise. Knowing that we’re going to learn about something unexpected makes planning difficult.

We like having some structure, but we also want to leave some space for spontaneity. We’re certain now that people we meet are going to insist that we visit their special places, and we know we’d regret skipping them.

Two years ago, I assumed we’d check off places and watch our list shrink. That’s not the way it’s working out. The great people we meet are always suggesting more destinations. Our travel list is growing longer and longer.

The late Susan Sontag said it best:

“I haven’t been everywhere, but it’s on my list.”

That’s why we have no plans to stop.


2016 – Digital Nomad Life After One Year

I’m running my practice remotely. I don’t go to the office. If you’re a regular reader, then you already know that I do it from the road.

Over the course of the last year, I’ve done my work in Berlin, Edinburgh, London, Lisbon, and the middle of the Atlantic Ocean on a cruise ship.

I’ve worked from Miami Beach, Las Vegas, and Denver as well as Hong Kong, Siem Reap, and Phnom Penh. We got quite a bit done while spending a few months in Vietnam visiting Ho Chi Minh City, Mui Ne, Da Lat, Hoi An, and Hue.

Most recently, we’ve been in Turkey, moving from Antalya to Kas to Istanbul.

Now, 365 days in, we’re in Verona, Italy.

We’ve moved quite a bit over the course of the year. We were warned that moving too fast might result in travel burnout. We decided that we’d risk it, and that we’d take more downtime if we felt like we were reaching our limit.

We’re likely to slow down a bit going forward. We’ve discovered that more time in one place is better than less. Time gives us the opportunity to settle into a routine and get to know the local people and services better. We enjoy a place more when we invest more in figuring it out. But we’re not locked into any particular plan or schedule. We’ll keep experimenting, and we’ll see how it goes.

We’re leaving Italy in a few days and heading to Ireland. One of our kids is doing an internship in Dublin, so we’ll visit and then head off to the countryside. We’re sticking around Ireland until early September. Then we’ll head over to Scotland for a month, after which I’ll visit America for a few workshops. Then it’s back to Southeast Asia for four or five months, followed by Jordan.

Below, I’ll answer some of the most frequent questions I’m getting about our lifestyle:

How’s It Going?

Working remotely isn’t new for me. I’ve been working from home and coffee shops since 2008. I like it. For me, adding travel to the mix has made it even more interesting and fun. I love taking walks in new places, and using our weekends to see local sights is an amazing opportunity. Having new neighbors all the time keeps it all fresh, new, and interesting.

How Is the Business Coping?

The business worked well with my remote work for a long time before I left the country. It continues to go well and grow. The biggest issue with “coping” has been time zones. For instance, when I’m in Asia, it’s hard to schedule voice calls, due to the extreme time difference. On the other hand, working without interruption results in more productivity.

Is It Like Vacation All the Time?

Sometimes yes, and sometimes no. We pick good spots, and, during our time away from work, there are awesome opportunities for exploring and adventure. We often have great views and great restaurants. But sometimes, it’s just head down, earbuds in, cranking away on the work. There are days when I have to stay focused and push onward in the face of a deadline. Those days don’t feel like a vacation. It’s just work in a different place.

Is It Stressful?

Sometimes, yes. It’s hard to maintain systems and routines when the setting keeps changing. That’s both a benefit and a detriment. It’s especially challenging when something goes wrong. Getting sick, dealing with unexpected stress or upset, or having a crisis of any sort is harder when you lack a routine to get you through the day. On those occasions, the stress level gets high, and it’s easy to miss the comfort of “home.”

Where’s Your Stuff? Do You Have a Home Base?

We sold most everything. We’ve got two banker’s boxes in storage in New York for our winter clothes and some mementos. We don’t have a base. Everything else that we own fits in our carry-on bags.

How’s the Technology?

The technology is pretty good. I’ve got everything working really well from anywhere, so long as I can get decent Internet. We’ve been in a couple of places where the Internet was incredibly frustrating, but we’ve overcome the issues by tethering off phones, finding better co-working spaces or cafes, or batching the work in some way that avoided the bad connection. We’ve found shockingly good connections in the weirdest places and shockingly bad connections in places you’d think would be speedy. But the connections are mostly fast, even in places off the beaten path.

How’s the Budget?

Shockingly, it’s great. We’re spending less now than we did living in Raleigh, North Carolina. In Southeast Asia, we mostly stayed in hotels. That area is known for being inexpensive. In Europe, we’ve stayed in apartments rented through Airbnb. Most of us think of travel as expensive. I think it’s expensive because we have very little flexibility, tend to go to popular destinations, and are forced—due to our schedule—to book expensive hotels. Lisa and I have been able to mostly take short, inexpensive flights on a flexible schedule, which reduces the price. Also, many of our flights have been free as a result of my interest in the points-and-miles hobby. We’re also getting long-stay discounts on housing. Most significantly, we’re not hanging out in places where prices are driven up by the popularity of the destination.

How Does It Feel?

Mostly, it’s a blast. I’m in my element bopping between places and cultures. I never tire of the novelty. I’d give it two thumbs up, with only a few qualifiers. Two issues come to mind.

  1. The biggest downside for me is having less control over work. When something comes off the rails, I feel less able to fix it. Between the distance, the time zones, and the technology, there’s a disconnect that makes it hard to repair a situation immediately. I have to talk myself through being comfortable with the speed of getting things back on track.
  2. The other issue for me is that it’s harder to read people when you’re 10,000 miles away. Misreading people can make bad problems worse. I can’t always detect subtle emotional cues in employees, vendors, and advisors when we’re on videoconference instead of sitting across from one another. That’s challenging, and sometimes results in miscommunication growing into upset.

Having Any Second Thoughts?

Nope. We’re still loving our adventure and plan to keep on rolling. If you’d like to come along, please follow me on Facebook and Instagram, where I post regular updates and pictures.

Anything Unexpected Happen So Far?

Most every day, there’s something unexpected, whether it’s the police in riot gear surrounding protestors, having dinner with a guy who turned out to be a Google Ventures partner, or meeting someone who hooks us up with “her guy” who finds us an apartment in a magical city we’d never heard of before. There were the hours we spent talking to the guy who saw most of his family killed by the Khmer Rouge, and the chicken that attacked me in the street. Something unexpected happens before lunch most days.

Any Plans to Settle Back Into a Non-Nomadic Existence?

Nope. It’s going well, we’re having fun, and we’re getting our work done. We’ll keep going so long as those conditions continue.

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