Traveling Full Time as a Remote Worker

Is not for everyone

We’ve all read the articles about the individual or couple that set out on a nomadic journey. They live out of a van or hostels, indulging themselves in cultures and experiences. They work remotely, making more than enough money to fund their journeys. At the end of it all, they come out enlightened and can never see themselves living in one place for long ever again. I took one of those journeys, but my experience was different.

Last year, my wife and I packed up nearly all our belongings, put them in a storage unit, piled into our SUV, and drove from Portland, Oregon to Seattle, Washington. This was the first stop of 15 during our 5 month nomadic journey. During those 5 months we worked full-time, taking off a handful of days to extend our weekends. As wonderful as the journey was, working the entire time dulled the experience more than I was expecting. 

Before setting out on this adventure, I had been a remote worker for about 10 years. I mainly worked from my home office. Occasionally, I'd work from coffee shops and the kitchen tables of family members. I almost always had the ability to go back to my workstation, plug my laptop in, and do the bigger work in my safe space. When your safe space no longer exists, it throws off your flow. If you wondered why you didn’t see a newsletter from me in the past 5 months, that might be why. 

This trip was not done on a whim. My wife and I thought about this trip for a long time. It was something we envisioned, developed a practical need for, and made into reality. The underlying ethos was that the United States has so much to offer, with most of it within driving range and worth exploring. The practical need was different. Our apartment lease was ending and we were not sure if we should call Portland home for the foreseeable future. So we combined both ideas into one trip. 

To preface, my wife and I are both remote workers. I work for myself as a consultant and she works for an agency. This allowed us the freedom to even try this. 

The Journey

We set off from Portland, Oregon on November 11, 2023. We packed up a storage unit with 99% of our belongings and put the rest in one large suitcase, one small suitcase, 2 backpacks, and a few loose items in the trunk. We have a Volkswagen Taos, it’s a small SUV, but the perfect size for this journey. 

We ended up slowly heading North through the Pacific Northwest, stopping in Vancouver, Canada. We then headed back down, stopping in half a dozen places in California. We went east, through the desert, stopping in Colorado. We hopped on a plane and stayed in Raleigh, NC. Finally, we flew back to Colorado and drove south to Texas to visit family and then flew to Florida to visit more family. This journey ended March 19, 2024 back in Portland, Oregon. 

If you want me to go into the details of every location I stayed, please comment on this post or reply to this email. I might write something that covers some of the locations. 

I learned a lot on this trip. How to travel efficiently and comfortably. How to work as a nomad – tools, software, and working styles. If you are thinking about setting out on your own nomadic journey, I have some tips for you that might make the process more enjoyable. 

Efficiency

We read the blogs and travel guides, but none of them aligned with how we wanted to travel. We had an idea of what that looked like, but the method we settled on was different. We wanted to spend 2 weeks to a month in most locations, so we could live like a native. Get past the initial “getting used to it” stage and really know an area. The best way to do this is to walk, bike, and get lost in a neighborhood. Meandering block to block allows you to interact with the people around you, find hidden gems, and see the best and worst parts of it. While we did stay in a few places for more than 2 weeks, this didn’t feel like a good use of time after the first few. 

Our method was – three days or less = hotel, four days or more = Airbnb. The main reason for this was laundry. We needed a washer and dryer, within reach. This allowed us to work and do laundry at the same time and not waste hours at a laundromat. Yes, most of you are probably thinking about sleeping in your car or couch surfing with friends or internet acquaintances. While those are options, they were not options for us. I was not traveling as a single 20 something, I was traveling with my wife and we are in our mid-to-late 30s. As much as people don't like to admit it, bodies age, and sleeping in strange circumstances does not bode well for someone my age. 

My wife and I also enjoy taking care of our physical health. We generally lift 4-5 days a week and exercise at other capacities 5-6 days. To make this happen we found a few nation-wide gyms we could join. We did this through Active and Fit, a service that was provided by our health insurance. It allowed us to sign up for multiple gyms for a flat rate. This allowed us to have access to fitness equipment and a guaranteed mechanism for getting to know a city or neighborhood. 

Since we were working full-time. We tried to always find lodging with some form of working area. In some places that was a large dining room table, a kitchen island, or a dedicated desk. We missed our standing desks and monitors the entire time. We did find a few Airbnb's and coffee shops with standing desks, but it was rare. Even fewer Airbnb's offered any form of external display. 

The biggest expense while traveling like this is not the lodging, it's the food. We made sure to find places with full kitchens. This allowed us to go to the local grocer and pick up food for meals. We set rules around going out to eat. We decided that we could eat full meals out 1-2 times a week and grab coffee/snacks 2-3 times. This is a bit of a trade off. While it does save the most money, food shows a city's culture, so going out less often exposes you to it less. 

We were driving from city to city and state to state, so we also set a driving rule. We could drive no longer than 6 hours in the car. Any longer would make us feel like shit and not allow us to travel on weekdays. 

Comfort and Affordances

We brought way too many items of comfort when we first set off. Luckily, we passed through Portland coming down from Vancouver, Canada. We promptly dropped off anything extra at our storage unit. 

Comfortable sleep is something that is always important for us. While we could not pre-test our beds, we were able to bring pillows with us. We brought around a few pillows and packed them in vacuum sealed bags during our trip. This gave us some semblance of normality to our comfort, even when the beds and bedding changed regularly. Sure, it is not our wonderful king sized bed, but it made a difference. 

Clothes are the biggest affordance on a trip like this. The biggest challenge for us was that we were traveling over a period of 2-3 seasons, across many environments. We traveled from cold and wet to dry and warm numerous times over the months. Since we were working out full time, we needed gym clothes. We also had a wedding to go to, right in the middle of the adventure, which required a bespoke wardrobe just for that occasion. I ended up going down to one pair of shoes, a handful of shirts, pants, and shorts. I only had 3 workout outfits. Plus, one thin coat and a few sweatshirts. My wife had a similar wardrobe.

Comfort is something that you have to part with on a trip like this. Personally, I am very particular about my comfort. I take care of myself by exercising, stretching, and eating well. Not being able to rest, sit, and stand comfortably made this trip challenging. Some might think this is just me being difficult, but it’s not. Once you get to a point of physical health that you feel good, I mean really good – you’re flexible, strong, you have minimal aches, standing isn’t a chore, and you don’t grunt as you sit or stand – being in situations that make you uncomfortable make you frustrated. Over months that frustration can compile. Try to find ways to mitigate that, however you can. 

Productivity

While I hate using the term productivity, I think it is somewhat purposeful in this context. Mainly because over these 5 months, I did not have the ability to work intentionally or foster creativity. I was brute forcing my way through my work, which ended up exhausting me sooner than I thought. 

I love to write, hence this letter. I love to curate my PKM and distill learning into new ideas and questions. I love to photograph and design. While traveling full time, I didn’t have the mental space to pull any of that off and in turn it leaked into my work, my “productivity”. 

Rather than recommending hardware and software, which was in the first 3 revisions of this letter, I recommend intentionality. While working nomadically, don't plan to work 8 hour days. Switch to a 4 hour workday and enjoy the experience. If you don't have that ability, this adventure won't last long or your work will suffer. 

Find your most productive time of your day, for most people this is when they first wake up. Set this time 100% for work. Focus on your most challenging task first and knock it out. Once the energy rush wears off, do some admin work – email, Slack, and other communications. Check off the light-weight, high-impact tasks on your list. 

Depending on your autonomy at work, group your meetings and other work at this time. Get all 4 hours done. If possible, do this really early in the day, 6-10 am. If you don't have that autonomy, then split it up – 2 hours in the morning, followed by 2 hours after lunch. Taking these gaps or focusing it all into one block, when you are at your peak, will allow you to do more work and more impactful work faster than you thought. Again, this requires trust and autonomy from your employer or clients, but it works, with diligence and practice. 

With your new found time, you can save that space for the things that fuel you, the things that you love. Some days can be used for exploring that new city. Others, it can be used for street photography of that city. Maybe you can sit at a coffee shop and write, design, or think; rather than getting a project done or taking a video call. Working so little a day might not seem sustainable, but it is the best way to find time for yourself, whilst not eating away at your travels. 

For those seeking the more practical tips, I do have a tech load out recommendation. Bring the least amount possible. Both for the weight and size of it, but also the constraints. Bring the largest screen laptop you have, especially if you are used to using a monitor when you work. I only had a 13" MacBook Pro M1, so I paired that with my 11" iPad Pro. This was essential for the days I needed to facilitate workshops, as I could have chat and peoples faces on my iPad, with the screen share on my laptop. I also recommend bringing a stand for your laptop, I think the Roost laptop stand is a perfect balance in size and functionality. Also, do not leave your keyboard and mouse at home. If you are a trackpad person, Logitech recently released a very cool option – The Casa Pop Up Desk. 

While on this trip I had the ability to see more of the United States than ever before. I realized how much there is in the US and how diverse it could be. I also realized that I do not like working full-time while traveling. Of course, I will have to work while traveling in the future, but I will not do it to this extent again. I plan on working less hours a day, maybe even less days a week. I don’t plan on starting a trip again without having a homebase. I also think I’ve seen enough of the US and its major cities for now. Most future domestic travel will be for National Parks and all international travel will be for art and culture in old, history-rich cities. Other people might have had different experiences, I am glad, but after 5 months of working and traveling I know it’s not how I’d want to do it again. And if you are wondering, I am very happy to be back home in Portland. I cannot imagine living anywhere else.