Experiment Report: My First Month As A Digital Nomad

If you’re a regular reader of this blog than you know I love experiments! I’m currently in the midst of a 4-month experiment where I am traveling with a group of digital nomads on Remote Year.

I designed this experiment to explore a longstanding question in my life about travel: would I enjoy a fully nomadic lifestyle?

Travel is one of my favorite hobbies, it’s my single greatest container for growth, it’s the vehicle in which I engage in experiential learning, and it’s been a tremendous bonding experience for my closest relationships.

Traveling is such a priority that my husband and I plan our lives around it. For example, in 2011 we moved from Chicago to Detroit so we could have our home base in a city with a low cost of living. This domestic geoarbitrage enabled us to use what we saved in housing costs and property taxes to fund our travels.

Currently we spend every December in Mexico for our annual retreat. Our winters (January – May) are spent in Venice Beach, California. And we plan several short international trips throughout the rest of the year (e.g., last year we visited Bhutan, Italy, Germany, Nepal, Switzerland, Tibet, and Thailand).

We plan our lives around traveling because of our annual planning process. During that process, we envision our optimal life in terms of our relationships, purpose, health, and growth.


And when it comes to experiential growth, our vision is that:

we visit the most magical and mystical places on earth and live in the most inspiring locations.

For most people (including my husband), 6 months per year of travel is more than enough. But I have found myself desiring more travel and have a long list of places that I want to visit and live before my time on earth expires. And the older I get, the stronger my motivation for seeing new places, meeting new people, and learning about how other people construct meaningful lives.

While I went through my own post-retirement transition process after we FIRE‘d, I’m still conducting early retirement experiments. So this summer, I designed an experiment to focus on answering my burning travel questions: would I enjoy making travel a lifestyle (instead of a scheduled activity)? In other words, what would my life be like if I became a digital nomad?

Designing an experiment to answer this question was quite easy because there are plenty of programs that allow travelers to try the digital nomad lifestyle. It was just a matter of picking one that best fit my needs, inviting my boo to join me (he declined), registering, and packing my bags.

I chose Remote Year for my experiment to test the following hypotheses:

  • Hypothesis #1 :Traveling more than I currently do will increase my happiness.
  • Hypothesis #2: A different pace of traveling (a new country every month) will be more satisfying than our current pace (several months in the same place every year and a few short multi-country sprints).
  • Hypothesis #3: Traveling with other nomads will enhance my travel experience.

My Remote Year cohort consists of 22 humans, ranging in age from 26 – 71. We are mostly American, slightly more women than men, and I am one of only 2 married people (both of us are traveling without our spouses). Every month our group is supplemented by several “citizens” (Remote Year’s term for alumni) who join us in a specific city for the month.

Our travel itinerary is as follows:

  • June: Split, Croatia
  • July: Lisbon, Portugal
  • August: Valencia, Spain
  • September: Cape Town, South Africa
Split, Croatia

I set off for Croatia in late May to join my Remote Year cohort (we are called “Davinci”). During the first month, I shared a flat with two men (who were delightful flatmates). If you’re curious what our flat looked like, here’s a short video tour:

As of this post, we’ve completed our first month of travel in Croatia. It was a month full of adventures, challenges, and growth including a whole bunch of firsts for me:

  • Zip-lining over Cetina Canyon
  • Presenting in the Pecha Kucha format
  • A romantic holiday with my husband in Venice, Italy
  • Attending the wedding of dear friends in Vittorio Veneto
  • Side trips to London, Oxford and Stratford-upon-Avon
  • Seeing the gender-reversed version of Taming of the Shrew at the Royal Shakespeare Theater
  • Attending FI Chautauqua
  • Reading great books by people I connected with this month (The Simple Path To Wealth by Jim Collins and Smart Investing by Sun-Jung Choi)
  • Birthing a brand new idea for a philanthropy project and getting immediate feedback on it from likely participants (and then iterating….) and
  • Completing the 30 Day Alcohol Experiment

In the midst of all those firsts, I’ve also learned quite a bit about myself. I’m not judging any of it as good or bad, just recording it as observational data. For example:

  • I prefer quality over quantity of experiences
  • I’m more people-curious than place-curious
  • I feel JOMO (joy of missing out) more frequently than I feel FOMO (fear of missing out).

And the biggest challenges of my first month have been:

  1. Navigating the reality that I’m not drinking alcohol, but alcohol consumption plays a central role in group bonding and most evening/weekend activities.
  2. Realizing that I grossly underestimated how much alone time I need to re-energize on a daily basis. I said “yes” to too many activities, got drained, and then got sick at the end of the month.
  3. Acknowledging that I felt homesick a lot of the time. This is the longest I’ve been away from my husband in our 24 years of marriage. Even though we Skyped on a daily basis and spent a few days together in Italy, I missed him (and the life we’ve created) terribly!

I’m only one month into the journey, so it’s too soon to tell whether my travel hypotheses will be supported (or fail to be supported) by my data. But as we move on to Lisbon, I’m making a few adjustments to align my travel experience with who I am as a human being. Specifically, this month, I’m:

  1. shifting from a shared flat to a private flat,
  2. reducing the number of group activities I do each week (so I can fully enjoy those activities and better balance group-time and alone-time),
  3. planning to be more pro-active about meeting local people who share my interests (books, writing, entrepreneurship, personal development…)

The most important lesson I learned this month is that even though I’m traveling with a group, I am 100% responsible for my daily experiences. On the days I was clear about who I am and what I want, I had an amazing experience. And on the days I went along with the crowd, I ended up exhausted.

I hope that my transparency about what life experiments actually look like (the good, bad, ugly and beautiful) will help those of you designing them for yourselves.

Warmly,
Kerry Ann

p.s. – if you have any questions about Remote Year, the details of nomad life, living in Split, or designing life experiments, post them below!

5 Replies to “Experiment Report: My First Month As A Digital Nomad”

  1. This was so fun to read as I am so interested in creating this same type of experiment for myself (wanting to give up our place and go live in a different country each month).

    I am curious how you are planning to meet more locals this month who are interested in writing, books, entrepreneurship etc? Will you be attending specific events?

    1. Hi Kristen!
      I’ve been meeting more locals this month a few different ways. The easiest has been through AirBnB “experiences” (local people create opportunities to do cool things) so it’s been a good way in the first few days to learn my way around the city, get an insider perspective, and make friends. Here in Lisbon, Meet-up is very active! In particular, there’s a “Lisbon Digital Nomads” group that hosts several events every week. And there are a ton of local meetup groups for every interest imaginable. I’ve also enjoyed “eat with” (www.eatwith.com). Local people host dinners in their home and you go and “eat with” them. No professional chefs, just good simple food and great conversations.
      Also, I have to say that I try to be friendly and talk to people when I’m in places where I have interests (like bookstores).
      People I’m traveling with are taking dance classes at local studios, showing up and performing at open mic nights, playing in soccer pick-up games in the park, etc… I think that music and sports are the easiest ways to meet people!
      Finally, our coworking space is included in our monthly fee. But if I wasn’t in this program, I would find a big, centrally located co-working space. They are popular with entrepreneurs and the bigger ones host events which are great ways to connect with local start-ups.
      I think the key is to ask people wherever you go what the best local resources are and then just get started. The conversations you have in any one place will lead to new resources, new things to do, and new people to connect with!

      One additional resource I found that I thought was amazing was the emergence of “coliving” communities. If you don’t mind sharing, these would make an amazing home base in a city. I attended a talk by the founder of this one in Tenerife: https://www.ninecoliving.com/

      Hope that’s helpful and I would love to know more about how you plan to structure your travels!
      Warmly, Kerry Ann

  2. Oh my gosh! This is so amazing and enviable. Congrats on going for it and giving it a try. I can’t wait to see what is in store for you over the next few months and what answers you come across regarding your hypothesis.

  3. I really need downtime and alone time or else I feel my glitter starting to lose it’s sparkle. But I still have a hard time pulling myself away from good conversations! It was awesome to hang out with you in the UK!

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