A “Digital Nomad” Experiment


  • Life as a digital nomad requires you to minimize stuff so that you can increase the possibility of new experiences.
  • For many people, the increased opportunities far outweighs the nomadic life “tax” for a season of life.
  • A digital nomad lifestyle is a great way to figure out your preferences, interests, passions, and values, but generally is not the best way to pursue what you discover. Most digital nomads settle somewhere to build community.

I became intrigued by the digital nomad lifestyle in the 1980s. I got to know a number of the early digital nomads, and follows many more via blogs and websites. My minor claim to fame was that Rolf Potts noted one of my travel light provided useful information in his book Vagabonding. The majority of the people I got to know “settled down” after 2-4 years, almost all within 10 years. The most cited reason for “settling down” was because they had discovered what was most important to them was deep connections, and that the best way to pursue that was to live someplace where they could build a community. An example of this is Mark Manson who wrote a piece about his experience as a digital nomad and after 8 years settled into a city. Four Thousand Weeks (chapter 13: The Loneliness of the Digital Nomad) has insights into how external constraints can make it easier to build community resulting in greater joy.

I have experimented working as a “digital nomad” over the years though I have spend the majority of my time living in my “home base”. In the last couple of years I lived as a nomad in Portland, Charlotte, Ashville, Denver, and Santa Cruz. Next will be several locations outside the US. I have no desire to be a full time digital nomad, though I think it’s a great way to experiment with a more minimalist lifestyle. I often leave most of my stuff packed away, using the same things “at home” that I use when traveling. I have been using my “nomad” trips as a way to explore new cities to determine if the next season of life will continue to be based in Mountain View, CA or new city. Rather than reading about possible locations I believe it’s better to check out a location for 1-2 months to get as sense of an area and then lived there for 6-12 months before making a hard commitment.

The first half of 2022 our home was going to be under utilized due the household (except me) taking an extended trip to see family in Taipei, an extended vacation in Europe, and spending time in Santa Rosa to work on a property. This seemed like a perfect time to let someone rent our home via AirBnB which would provide net positive cashflow while provide an opportunity for me to further experiment with a digital nomad life. I work full time for HashiCorp, a remote first company which makes it easy to live pretty much anywhere. Much of my work is meetings with people who are primarily in timezones associated with the Americas which encouraged me to stay in those timezones.

As previous trips, the core of what I will use fits into a 23l, carry-on size bag. I am staying in AirBNBs which have a kitchen so I can prepare my own meals. Originally I was thinking spending the first month in San Jose Costa Rica, but that isn’t going to work out. I will have to try Costa Rica at some later date. Over the next four months I am staying in seven places, three cities, not counting our vacation. The following is a combination of the lessons I learned on past trips and current trips.

There is a “moving” tax

Each move requires around five hours beyond the actual travel time. This includes time to clean out fridge and pack, load/unload baggage, assess a new place, unpack, and prep a new kitchen for real cooking.  Emotionally, it seems like it takes two or three days to adjust to a new physical location, and maybe a week before life within the abode is fully settled.

There is a “new” tax

We have refined / optimizing our home and life to support our activities. The utensils we use are easily accessible in the kitchen.  Supplies are ready to go and near where they are used. We know the most efficient path to destinations, where to acquire everything needed, what parks have easy access / adequate parking, safe bicycling routes, etc. Daily friction has been minimized.

Each geographical location change requires several weeks to adjust on the basics. During the first couple of weeks normal “life maintenance” activities like getting groceries, exercising, etc take significantly more energy than when doing these activities in a location that is well known. For example:

  • groceries shopping requires you finding a store has the products you are looking for (some of which might not be available in any of the stores) and then you need to figure out the stores layout. What is a 10 minute frictionless trip to a “home groceries store” could be a 30 minute exercise of frustration which results in only part of a shopping list filled.
  • running requires finding a good route. Once you have a new route you need to memorize it. Eventually you might have enough context to be able to improvise your routes. When home it’s possible for the run to be almost fully on automatic, allowing the time to be focused on the experience or something you are thinking about rather where is the next turn I need to make, oops… I missed it, can I continue this way or do I need to backtrack?

After the first few weeks the most common activities will proceed smoothly, but there will continue to be friction each time you try to do something that you haven’t tried in the new location.

I know people who move daily or weekly. That wouldn’t work for me. I would want to spend at least two month in a location which provides time to get through the learning curve and to have time to enjoy a location.

Sidenote: High quality Internet service is critical. I have been spoiled by AT&T Fiber. When Internet service has been flaky (thanks Comcast) it really disrupts productivity and produces significant stress which spill into all of life.

Need “Recovery Time” from “Work”

In the last two years my work has been filled with a lot of collaborative meetings over zoom. While I typically feel energized when meeting in person, meet over zoom typically leaves me feeling emotionally exhausted. Others have written about the cost of zooming. When “daily life” doesn’t have a lot of friction, it provided time for me to “recharge”. I could then jump into “fun” without realizing that work had taken a fair amount emotional energy.

The “new” tax resulted in my daily activities often costs emotional energy rather than provide a time to recharge. As a result it’s hard to really “enjoy” a new location on the days I am working. I discovered that it was hard to even enjoy eating out on workdays because when I am tired from work it’s hard to eat healthy food.

During a vacation I can enjoy a “go-go” agenda filling up almost every spare moment. It’s different when I am working remotely. On the days I am not working (the weekend) I need some time to recharge. I have been able to enjoy my new location, but I only have energy for a few activities or experiences. Then I need a recharge so I am ready to work the next week.

I can explore an area more completely in a couple of weeks during a vacation than a couple of months while I am working.

Workspace matters

For much of my professional life, I have done a fair bit of work using a laptop which was actually sitting on my lap. I could sit in our living room or anywhere that had a comfortable chair or couch.  I have come to realized that when I was doing that work,  I was typically doing focused work. Real-time collaboration was typically not required. When I needed close collaboration I would go into “the office”.

In the world of remote work I have found that my laptop screen does not have enough real-estate. I need at least a second high resolution screen which can hold “my work” while the laptop screen is used for video conferencing. At home I use a 27 inch 4K display mounted right above my laptop which works quite well.

When traveling I initially tried using an iPad Air via Sidecar as my second monitor, but that didn’t work so well. First, I want more real estate. Second, I found that the connection to the iPad was unstable and I had to reset it several times each day due to marginal WiFi in many AirBnBs.  Later I realized I should have used a USB to tether the iPad. I switched to using a portable 14” 4K display which is tethered to my my laptop via a USB-C cable. I have found the portable screen’s connect is stable and it’s lighter and more transportable than an iPad. Displaying at full resolution makes the characters too small for my poor eyes, so I scale the display. I don’t have a way to mount it above my screen, so it sits to the side. When I look at it – for example when taking notes during a meeting, I am looking away from the camera on my laptop which can mis-communicate that I am not paying attention. I now know there are second screens that can attach to my laptop. If I was flying between locations I would make do, but since I was driving between locations, I retrieved the folding desk I use at home and my 27″ monitor which easily fit in our car’s trunk for transport. The desk is small enough I can set up just about anywhere. This allows my workspace to be just like home wherever I am.

When working remotely in a space that doesn’t have walls and door that separate me from others I find myself distracted and not able to focus fully on the people in the virtual meeting. Using earbuds/headphones can lessen this need, but I find myself very self conscience in these situations which impacts my ability to be present, and focus on the people I am meeting with.  I learned of the article “The invisibility cloak illusion: People (incorrectly) believe they observe others more than others observe them” from a Hidden Brain podcast which reinforced my concerns of doing private things in public spaces. My solution now is to only book locations which proves me with a work space that gives me walls and a door between me and other people.

The Challenge of Community

I value community. Regularly moving locations can make forming and maintaining community very challenging. I keep in contact with my closest friends with weekly “walking” phone calls. We have found talking while we walk in our neighborhoods or nearby parks works better than zoom calls. I think this is because zoom calls require us to process visual signals which is taxing, but the fidelity isn’t good enough to get useful signal.

As a nomad you will need to purposefully engage and initiate to find community. We have found that when we jump in, volunteer to help, initiate time that a fair number of people (outside the Bay Area) are happy to engage. Leverage your interests, passions, hobby, and professional networks to find community. The traveling entrepreneurs I know often look for workspace, professional societies, and alumni organizations to tap into. They have found that if they offer to host gathers for the group they are quickly welcomed. We have attempted to meet people via meetup.com (mostly hiking groups) and by attending a local church. We try a new church each week until we find one that practices grace and hospitality. Besides attending Sunday morning worship we will attempt to join some sort of mid-week activity to get to know people on a personal level. We expect most of the relationships we start will be short lived, but they have been rewarding. Ten years ago I wrote about how I discovered the benefits of being open to surprising relationships and still find this to be true.

One thing we really miss when being digital nomad is that it can be difficult to host gatherings. Many AirBNB agreements ban “parties” or even having a guest or two. It’s also challenging to find a reasonable cost airbnb which is well suited to hosting gathers.

Some people are using their nomad experience to build community. They do this buy staying in shared housing which is filled with other digital nomads. When they “click” with someone, they select their next destination as a team. Over time small clusters of people become a roaming band.

AirBNB Expectations

People have different standards. This can be obvious when reading AirBNB reviews. Some people talk about how nice a place is and how well it was cleaned, but others complain about the same location. While the conditions might be different I believe this is more of a reflection of people’s expectations. Some people are expecting the same sort of care found in high end hotels where every surface has been scrubbed by professional cleaners. Other people’s standards would be more typical of someone’s personal home. For example, most people would clean surfaces like counters, sinks, floors, etc on a regular basis, but generally don’t completely unload their cabinets each time they are cleaning their home.

Renting our Place Out While Nomading

Over the years we have simplified our “stuff”. This enabled us to box up and move most of our “personal” items into the garage in a couple of hours. There were a few pieces of art that we couldn’t replace which we moved into a protected space, one closet and one cabinet that we left personal items with with a sign which said “personal”. Otherwise we left all our family gear for our guests to use and enjoy. We have found guest generally treated out stuff with respect. A few things were broken, much like what would have happened if we were living at home.

We have experimented with what to leave in the fridge and cupboard. I though leaving our complete collection of spices, oils, staples, and maybe some goodies in the fridge would be appreciated. Jackie suggested just the bare basics would be better. I have come to believe Jackie was mostly right, that a much more curated and “fresh” set of supplies is preferred with the fridge being sparkling clean on the inside.

When people are staying in your place, everything that has ever been an issue for you, even if it happens only once every six months will happen to your guest within the first few days. It’s likely a few new things will happen that have never occurred in the past or you never noticed. It’s critical to have someone who is local, available, and can help care for your guests. Quick and friendly response is often more important than immediate resolution. Many of the issues were very simple. I expect that if people were in their own home they would have figured things out themselves and not asked for help.

People don’t read “manuals” or long documents. If you want to impose rules or restrictions it’s best to have something that convenes that “just in time”. For example, one place I stayed in put a small dowel which stopped a closet door from opening. This let me know that space was for their private items. The space didn’t need to be secured. I was going to respect their space. There were a few spaces in the same place that didn’t have this treatment which I mistook to be available to me until I later read the manual.

What I am  Using

I am using my typical travel/packing list with “high sweat exercise”, and “sunny” added. All of my “personal” items fits in a 23L daypack. Since I am often driving rather than flying between location I have decided to bring some additional items. I am bringing both my personal and work laptops (Apple MacBook Pros). For the first part of the trip I will have a 26L daypack filled with various documents and office supplies to prepare my tax return. I am bring some exercise equipment discussed below.

Finally, I am bringing some family gear which is also discussed below.


  • Roku stick. Nearly everyplace we have stayed has a smart TV with an accessible HDMI slot. Rather than having to configure the smartTV with our streaming services we just connect the Roku stick to the WiFi and immediately have all our content configured and ready to go.
  • Bluesound Flex Speakers: Configured as a stereo pair. Surprising good sounding for their size. Allows us to listen to music together without cringing at the sound quality of standard TVs or the speakers on the iPhone.


I originally decided to bring some fitness equipment to avoid having to find a gym. I am back to doing a slightly modified “simple 6” workout and riding my bicycle. Items carried include:

  • Withing Body Weight Scale: Isn’t letting me change it’s WiFi network. My solution was rename my iPhone to be the same as our home network, set the password to be the same as home, and turn on hotspot compatibility mode. This allows the scale to update via my phone’s Hotspot.
  • adjustable kettlebell
  • door-jam pull-up bar
  • bicycle
  • helmet
  • cycling shoes
  • Pump
  • chain lube
  • charger for bicycle di2
  • oLight magnetic battery charger for lights and power meter peddles

Transporting these items is a slight hassle. I would prefer heavier weights, but they won’t fit in the Mini Cooper. If I was going to be a digital nomad “full time” I would either need to development a body weight only workout plan or join a gym near wherever I was staying. For my last stay I joined a gym to get heavier weights, a rowing machine, and a pull up bar because my door jam bar didn’t fit where I was staying.

Kitchen, Food

I (later we) are cooking most of out meals rather than eating out. I am bringing a number of kitchen items which are often absent in the places I have stayed:

  • Kitchen scale
  • SodaStreamer + 1L water bottle (to avoid purchasing bottled soda water)
  • Sharp chef and paring knives (because most places have dull, crappy knives)

I am transporting whatever food hasn’t been consumed and a few staples in a folding cooler and a large re-usable shopping bag. Staples I am carrying:

  • Favorite teas
  • Red Pepper Flakes
  • Cajun Spice
  • Curry
  • Olive Oil
  • Good Balsamic Vinegar
  • Sliced Raw Almond (which I roast as needed) 
  • Mustard
  • Garlic
  • Ginger
  • Lemon Juice


I initially left my ChiliPad behind. Since I am by myself right now I can drop the temperature of the room I am sleeping in without making Jackie uncomfortable. I hoped this would let me sleep as well as I do with the ChilliPad. No such luck. I am finding that without the ChilliPad I wake up each time I transition from REM sleep and am less rested at the end of the night. This has confirmed to me that the ChilliPad is really been useful. Furthermore, my resting heart rate has been higher during this time. The second half on this journey I am using my ChiliPad and find I am sleeping better.

1 Comment

  1. Very good blog. I think we are all torn by two sides. On the one side, we are going stir crazy working from home and would love the change of scenery. On the other hand, home is so convenient as you have pointed out. At home, I have 3 monitors to do my work, and I find that even with 3 monitors, it is not quite enough so I cannot imagine working from another location without that. 🙁

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