Two 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 to only 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 it 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 drifted 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 roller bag after watching my wife traverse airports without sweating.

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

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

I panicked.

“What did she say?” I asked my well-traveled 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.

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(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 perspective, 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 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 so 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.

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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.

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