Interview with Keith Williams: Working Remotely from 34 Countries in the Past 3 Years

Meet Keith Williams, a senior engineer at Kopa. Keith makes our fully remote team extra special (besides being an incredible coder). He has traveled all over the world in the past few years. We sat down to get the full scoop and learn more about moving around every few months as a digital nomad, a term he doesn't like, by the way.

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What was your childhood like?

I grew up in Roanoke, Virginia [in the United States]. It's a place where very few people leave, and if they do, it's normally to move somewhere nearby, like D.C. or Charlotte. When I was a kid, we didn't travel much, but my mom traveled with my grandmother, and eventually, she also started traveling more for work and I started going with her.

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What did you do before you started traveling as a digital nomad?

I had a very typical Virginia life. I went to Virginia Tech, which was close to home. When I graduated, I got a full-time job as a software engineer at a company near Christiansburg, VA, where I lived at the time. I ended up working for that company for 10 years.

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When do you first learn about the concept of the "digital nomad lifestyle?"

In summer 2016, I decided I needed to experience something "more." I always wanted to live in a bigger city just to know if I would like it or not. I had to try it. I remember vividly: I was laying on our 15-year-old green couch at my parents' house and searched "how to travel and work remotely", hoping to find some travel programs where I could move to different cities. I stumbled upon Remote Year. After investigating their program, I decided it wasn't feasible to commit $26,000 and an entire year to try out this digital nomad life. So I then searched "alternatives to Remote Year" and found Hacker Paradise.

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What made Hacker Paradise so special?

I knew that when I left to travel internationally, I wanted to go with other people. The idea of Hacker Paradise was and still is extremely compelling: "Pack your bags, meet up with 25 other people from around the world, live in a different country, work together in a co-working space or at your apartment, have nightly activities with your working community, attend weekly Monday lunches, contribute to weekly potlucks, and take weekend side trips to your heart's content." It sounds too good to be true, but that's exactly what it was and exacted what I wanted — to meet people from all backgrounds who speak different languages and who think differently than I think. That's something life in Virginia couldn't give me.

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I know you don't like the term "digital nomad." Why is that?

I'm generally just not a fan of labels. They tend to give people, lifestyles, and behaviors a stigma. My intention is not to do this because I just "want to be different" or because other people are doing it or because I want to fill up an Instagram account with my smoothie bowls in Bali. I'm doing it because this is the life I want to have.

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How many countries have you visited?

I've been to 39 countries, and 34 of those were in the last 3 years.

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What are some of the most amazing things you've seen?

First things that pop into my head are:

• Na Pali Coast (Kauai, Hawaii, USA)
• Sunset from Haleakalā at 10,000 feet (Maui, Hawaii, USA)
• Sistine Chapel, where I've cried each of the three times I've been there by being overwhelmed (Vatican City)
• David sculpture (Italy)
• St. Peter's Basilica (Vatican City)
• A soccer match between Peru and Uruguay in downtown Lima, Peru
• Views from Lion's Head in Cape Town (South Africa)
• Rock formations in the Philippines
• The precision with which people operate and how they respect the culture and others in Japan

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You met your partner during one of your travels. How did that happen?

We met in Buenos Aires in January 2017, which was the very first week of my travels. I joined Mundo Lingo, a program that sets up events in local spots across a variety of countries. You show up and tell them the languages you speak and the ones you want to learn. Based on this, they give you flags that you stick to your shirt so people know if they should come to chat with you or not.

My friends decided they were leaving, but I stuck around for a few more minutes and that's when we met. I walked over and spoke terrible Spanish to her, and somehow it worked. We ended up going on a bunch of dates during my month in Buenos Aires, barely able to communicate. Thank goodness for Google Translate and body language.

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How do you handle being in a relationship and moving around?

It's been tough. The first few weeks of being apart are okay, but after about a month, it's hard to keep the energy going in the relationship. Fortunately, she now travels with me most of the time.

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What do you pack?

I'm one of the few seasoned travelers who still travels with a big suitcase, but I have plans to get a proper carry-on so I no longer need to check bags. The overhead and stress of checking a bag are no longer worth having a few extra black t-shirts.

Besides my suitcase, I carry my backpack with two laptops, endless amounts of cables, adapters, batteries, headphones, and of course, my passport. I also have universal adapters, a mini router with a built-in VPN configuration, a SIM card toolkit, and a portable charger.

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Do you try to learn anything about the countries before going?

Absolutely! This is the #1 reason I travel. I used to travel to do all of the touristy things. Now, I travel to experience a different life. This means learning at least some of the language. I'm almost fluent in Spanish, I speak enough Italian to order meals and get through small conversations, and I speak enough Japanese to shock some locals. My goal is to be fluent in Spanish, Italian, and Japanese and to be knowledgeable in French and Mandarin by age 40. I'm 33 now, so I have some years to go.

I love the idea that when you learn a language, you connect yourself with many more people. For instance, learning Spanish has not only been beneficial as the language used in my relationship but now I can also communicate with 400 million native Spanish speakers. That's pretty amazing.

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Do you go out for every meal, or do you cook at home?

We pretty much eat out every meal. It does get quite expensive, but I love trying local cuisine. I search for places with menus only in the native language because they tend to be more authentic and less touristy.

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How do you budget when you're surrounded by so many places to see and things to do?

I used to want to see and do everything. But now I've realized that tourist attractions are just a small piece of being somewhere. I'd rather go find a hole-in-the-wall bar and chat with the locals.

As far as a budget, I'm admittedly pretty bad about this. When traveling with Hacker Paradise, I try to watch my expenses because it's so easy to want to go out and about with the group to do things every day. Over a month or two months, that can start to add up.

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How often do you switch places?

It depends on how much energy and desire I have to move. Everything that goes into moving to a new location like finding a gym, finding a laundromat, and finding good coffee shops to work outside of the apartment can get exhausting and overwhelming. Generally speaking, I spend 4-6 weeks in a given location.

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How does your family feel about you being so far from home?

My family is extremely happy for me. They always knew I wanted something different than the life I was living in Virginia. They miss me, and I miss them. But when I go back, I stay with them at our family house for at least two weeks at a time — sometimes longer, and we make up for the lost time. In total, I spend about one or two months with them each year.

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What's been the hardest thing about moving around as often as you do?

Losing old friends. I try extremely hard to stay in contact with them and meet up with them when I'm home, but inevitably, some are not interested in continuing our friendship because I'm not around much. I understand that.

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How easy or difficult is it to make new friends while traveling?

Making friends is easy. Since this lifestyle appeals to a particular type of person, you are likely to meet people who have many of the same interests you have. This could be anything from enjoying to work in cafes, always saying "yes" to the wildest of trips or simply being open-minded and wanting to learn about the world.

Like my hometown friends, maintaining those friendships is the hard part. We have a saying amongst our friend group: "See you at some point in some part of the world." It's cheesy, but it explains our lives and our friendships. We know that we won't always see each other. We know that we can't call each other up to go out for a coffee in 15 minutes. But we do know that if we plan a trip to Vietnam or the Philippines, our friends will come.

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How has your team reacted to you working from across the world?

In the past, it has been challenging. I worked for a company where everyone on the engineering team was at the office except for me. Last year, I worked on a predominantly remote team that still believed if you lived in the Bay Area, you should come to the office every Wednesday. My travel made these situations difficult because people who wanted to be remote workers couldn't because of their spouses, kids, or fear, and they treated me differently.

Now, I work at Kopa, which has a fully remote team that appreciates that I live differently and in lots of different cities. It's a huge relief to have a team that supports this culture.

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How do you create your own schedule with teams in different timezones?

To prevent disrupted communication and maintain work dynamics, I stick to the timezones of the main team. When I was in the Philippines, I worked from midnight to 8:00 a.m. to match the workday of my team, which was based in the United States and Canada. This schedule sounds crazy, but I like it. I agree with that Herm Edwards' saying "Nothing good ever happens past midnight." I don't feel like I'm missing out on anything, and I enjoy having an entire day free to go to the gym, run, explore, get a massage, or try street food.

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What types of tools do you use to stay in touch with your team?

We stay in contact more often than the usual team. We use Slack and Google Meet as our go-to applications for communication. We try to check notifications somewhat often to make sure we're available to chat when needed. As a remote worker, it can be hard to disconnect fully from work. I try to turn off notifications during non-working hours so I can maintain some work-life balance.

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How do you feel about going into the office vs. remote work?

I would definitely work in an office again. While I lived and worked in San Francisco, I went to an office 1-3 days a week and worked remotely from home during the other days. I still love the idea of mingling with people, just like in Hacker Paradise. Working in an office has that benefit. You have the opportunity to get to know your coworkers which can potentially help with communication.

Having said this, for me, working in an office is a productivity drainer. If there is one thing I've learned about myself in the past few years of working remotely is that I love physically being by myself when working. This is a tricky part of working remotely because if you have significant others, friends, or others around you while working, you're just as subject to distractions—if not more—than being in an office.

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How has your view of traveling during remote work changed over the past few years?

I've gone from wanting to see and do everything in the Trip Advisor Top 10 List to now just wanting to live like a local. I love getting into a routine, even if only for a few weeks. I don't feel a burning desire to go see and do everything. When I find places I like and I feel comfortable in, I tend to go back and slowly check off the Top 10 List.

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Where do you classify "home" as?

Home is now technically Buenos Aires, Argentina. My girlfriend owns an apartment in the city and we are calling that home base when we aren't traveling.

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Where to next?

In just a few days, I leave Buenos Aires and head to Portland, Oregon, which I'm extremely excited about because I'll be spending time with our Kopa team at our company retreat. From there, I'll be in Blacksburg, Virginia; Florianópolis, Brazil; Buenos Aires, Argentina; Paris, France; Tokyo, Japan; and Francavilla al Mare, Italy.