My digital nomad journey: lessons I’ve learned (and relearned) working remote from around the U.S.

My digital nomad journey: lessons I’ve learned (and relearned) working remote from around the U.S.

Whether you call it digital nomading, location independent, extreme remote work or something else, this not-so-new lifestyle is something that a lot of new people are choosing. My best friend and I are two such people. We are living and working remotely from various places around the U.S. and learning a lot along the way. Fun times are also being had. Below I share some specifics of my digital nomad journey in the hopes that maybe they will help inform or entertain you.

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One of the very first things I learned on my digital nomad journey is that no two experiences are alike. You can read all the blogs and do as much research as possible, but you will quickly realize that there is no “right” or “typical” way to be a digital nomad. There is just you, your situation, and what works best for you. To give some context to the experiences and lessons described below, here are some of the specifics of my particular situation:

  • I have a full-time job in corporate America and have worked for the same company for over 15 years. I like my job and I am not looking for a different opportunity.
  • I am experiencing this lifestyle with my best friend, R.
  • I can work outside the U.S. but R cannot, so we are sticking to the U.S. (for the most part).
  • #vanlife is not for me. This adventure is happening courtesy of Airbnb and VRBO.
  • I still have a home base (thanks to loving and supportive parents) where I can get mail and store stuff.
  • I am 40 years old, single, and I have no kids. I also do not have pets.

The beginning of my digital nomad journey

I never gave much thought to becoming a digital nomad. I only heard the term for the first time a couple of years ago and it brought to mind twenty-something freelancers and social media influencers working from coffee shops. Although I love to travel, I also love my steady job with good benefits and security. So I did not give digital nomading more than a passing thought. Even when the pandemic hit and I began working from home for the first time in my life, I never gave any serious thought to changing my lifestyle. I still thought of digital nomads as young creatives and not someone like myself: settled in my career and approaching middle age.

However, the pandemic and working from home did convince me to try working from other locations. If I could work from my bedroom in Boise, why could I not work from a bedroom in another state? So I decided to try it out. Then I tried it out again. And again. Before too long, planning remote work trips was a given. And every remote trip I took, I learned something new. I did not know it at the time, but those lessons would come in very handy when I made the leap and became a fulltime digital nomad.

So many lessons learned and fun times had

It has now been two years since I first tried working remotely from someplace other than my house in Boise and I have learned (and relearned) things with every trip. I have listed those lessons below. Below that list, I detail my digital nomad journey and include some highlights from each location. Warning: the list gets longer and longer with every new place we visit.

  • Lesson #1: When you switch locations on a work day, you are not going to get a lot of work done.
  • Lesson #2: Working remotely is a skill that takes practice.
  • Lesson #3: Digital nomading is not cheap.
  • Lesson #4: Things will not always go as planned.
  • Lesson #5: Location, location, location.
  • Lesson #6: Keep consistent hours, no matter where you are working.
  • Lesson #7: Put everything important in your carryon.
  • Lesson #8: When it comes to choosing a location to work from, think beyond the obvious.
  • Lesson #9: You do not have to rent a car for the whole trip.
  • Lesson #10: Explore different modes of transportation.
  • Lesson #11: Schedule time to play.
  • Lesson #12: Do not hesitate to jump on a great opportunity.
  • Lesson #13: Good wifi is crucial.
  • Lesson #14: If the trip is short, stay in one place.
  • Lesson #15: Look for rentals that cater to longer stays.
  • Lesson #16: Pay attention to the weather.
  • Lesson #17: You may get homesick.
  • Lesson #18: Pace yourself.
  • Lesson #19: If you rent a bigger place and go somewhere cool, people may visit you.
  • Lesson #20: Take advantage of unexpected in-person work opportunities.
  • Lesson #21: Make sure the place has a washer.
  • Lesson #22: Gift certificates to local places make good gifts for digital nomads.
  • Lesson #23: Two weeks can be fun, but it feels a little rushed.
  • Lesson #24: Take advantage of Little Free Libraries.
  • Lesson #25: Digital nomading is easier with a car.
  • Lesson #26: Take pictures or a video of your abode when you first arrive.

Working remotely from Arizona and New Mexico (my first remote work trip and the beginning on my digital nomad journey)

Timing: two weeks in November

The first time I worked remotely from somewhere other than my house in Boise was both fun and a really good learning experience. I made a plan to visit and work from four cities over the course of two weeks. The cities included Tempe, Tucson, Santa Fe and Albuquerque. I planned this trip like I plan my vacations. This meant I had a lot of fun. However, I quickly learned that some of my plans were not conducive to being productive at work and living like you are on vacation is not sustainable by any stretch of the imagination. Still, I have no regrets. It was a great start to my digital nomad journey.

Fun times that were had on my digital nomad journey to Arizona and New Mexico:

  • Exploring Saguaro National Park. I particularly enjoyed catching the sunset.
  • Meeting up with friends for dinner near Tempe, Arizona.
  • Breakfast and a walk through the Casa Grande Neon Sign Park in Casa Grande, Arizona. 
  • Driving the Turquoise Trail and shopping along the way.
  • Staying in and exploring Santa Fe. Even though we got there right before a shutdown (for covid), we saw and explored a lot.
  • Discovering Duran’s Pharmacy in Albuquerque. This place is awesome. It also happened to be one of the few places open during the shutdown.

Lessons I learned from my first remote work trip to Arizona and New Mexico

Lesson #1: When you switch locations on a work day, you are not going to get a lot of work done.

This concept seems obvious, but it completely skipped my mind when I was making plans. (Remember, I planned this first work trip like a vacation.) So I learned that when you try to switch locations on a work day, you are either going to be physically changing locations and unable to take phones calls and respond to email, or you are going to be displaced without a good place to do your work (i.e. checked out of one lodging by 10 a.m. with a check-in time at the new lodging around 3 p.m.). If it is the latter, sure, you can go to a coffee shop or some place similar. But I would venture to guess that you will not be doing your best work.

For this first trip, I ended up physically moving to a new location twice in the middle of the week. I am not sure what I was thinking, but very little work got done on those two days because I was in a car for several hours. When we stopped for breakfast at Casa Grande on one of those days, I did call into my department meeting. But I ended up having to use vacation hours for the rest of the day. Taking time off was not a problem, but it was not very good planning on my part and an important lesson to learn early on on my digital nomad journey.

Lesson #2: Working remotely is a skill that takes practice.

The first two days I worked on this trip were hard. My brain was in vacation mode and it did not want to be sitting in front of a computer for eight hours while there were so many fun things to do outside. I immediately worried that I was not cut out for working in fun places. Thankfully, things did get easier. In fact, I continued to get better at working remotely the longer I did it. Now I don’t think twice about it. When it’s time to work, I work. When it’s time to play, I play.

Lesson #3: Digital nomading is not cheap.

This is especially true if you have a permanent residence. You are essentially paying for lodging twice. Add in flights, rental cars, eating out, shopping, etc., and the expenses add up real fast. Since I planned this first work trip like a vacation, I spent money like it was a vacation. It was fun. A lot of fun. But I came home knowing it would be some time before I could do it again since I needed to save some money. Even if you do not play as much as you would on a vacation, traveling in general can be expensive.

Lesson #4: Things will not always go as planned.

You cannot always predict what will happen in your new home. Unfortunately, by the time we arrived in New Mexico, the state was planning a second lockdown related to covid. We had a couple of days of fun, but then we lived under restrictions just like the rest of the state. Luckily, we could still spend time outside and we did a lot of exploring on our feet. But it was disappointing and really limited what we could do.

Two shadows in Saguaro National Park on the first trip of a digital nomad journey
Exploring Saguaro National Park after work.

Working remotely from the Mississippi Gulf Coast

Timing: one week in February

The second work trip we embarked on was to the Mississippi Gulf Coast. Pass Christian (or The Pass) to be exact. This was a birthday trip for me. I enjoy visiting the south, but the time it takes to get there from Idaho discourages any sort of long weekend or micro trip. It took me some time (I’m a little embarrassed to admit how much) to realize that working from a location in the south meant I could extend my trip. But once I did, I opted to stay and work in a location I had only driven through but wanted to explore more: the Mississippi Gulf Coast. The plan was to stay a week over my birthday.

Fun times that were had on my digital nomad journey to the Mississippi Gulf Coast:

  • Eating fresh seafood and southern cuisine. Yum, yum, yum.
  • Walking along the coast anytime, but especially during my lunch hour.
  • Experiencing warm temperatures in February (I even got a sunburn).
  • Exploring and shopping in small coastal towns like Pass Christian and Bay St. Louis.

Lessons I learned working remotely from the Mississippi Gulf Coast:

Lesson #5: Location, location, location.

If you do not rent a car, make sure there is good public transportation. We did not rent a car and this beautiful little spot has terrible public transportation options. So we had to rely on Uber and Lyft and they were not particularly reliable. We also walked a lot. It was difficult to explore and looking back, it was the kind of place where you need a car. Thankfully, there was a Walmart half a mile away where we could buy groceries. We also picked up some necessities when our luggage was lost. Without that, we would have been really challenged staying in this location without a car.

Lesson #6: Keep consistent hours, no matter where you are working.

Staying on Idaho hours works best for me and my team. It can be a little confusing when R and I are making plans outside of work, but sticking to a consistent schedule has made the transition from location to location just a little bit easier.

Lesson #7: Put everything important in your carryon.

This includes your computer’s charging cord. Our luggage was lost on the way to Mississippi and it took a couple of days to get it back. We were able to replace toothbrushes and face cream easily enough, but R’s charging cord for her laptop was another animal. Thankfully, she was able to use mine while I was off galivanting on my birthday. But it was an important lesson we will not soon forget.

Two palm trees at dusk on the Mississippi Gulf Coast.
Walking along the Mississippi Coast during my lunch hours and after work was a highlight of this work trip.

Working remotely from Little Rock, Arkansas

Timing: one week in May

Work trip number three was to Little Rock, Arkansas. The best part about this trip was that Little Rock was not on the radar for either R or me. But plane tickets were affordable and there were Airbnbs available near downtown. We looked at each other and said, “Why not?” That led to a lot of research and a really fun week playing and working in Little Rock. We also rented a car for part of the trip and explored Hot Springs, Arkansas.

Fun times that were had on my digital nomad journey to Little Rock, Arkansas:

  • Exploring Hot Springs National Park and the surrounding town. This place is really cool.
  • Getting spa treatments at Quapaw Baths and Spa.
  • Digging for diamonds at the Crater of Diamonds State Park. Unfortunately, we were not successful at finding the mother lode.
  • Enjoying all the southern food. Did you know Little Rock is famous for its cheese dip?
  • Being humbled at the Little Rock Central High School National Historic Site. This site is a must-see for anyone coming to Little Rock in my opinion.
  • Exploring Little Rock and the capitol building.
  • Getting educated (and shopping) at the Esse Purse Museum. It was right down the street from our Airbnb.
  • Riding scooters for the first time. I may have gotten distracted from the experience by two police officers on horseback. I love it when horses are part of a police force.

Lessons I learned working remotely from Little Rock, Arkansas:

Lesson #8: When it comes to choosing a location to work from, think beyond the obvious.

Like I mentioned earlier, Little Rock was not on my radar. But it was such a fun trip and a place I would highly recommend. Finding gems like Little Rock is a big draw for me on this digital nomad journey.

Lesson #9: You do not have to rent a car for the whole trip.

Remember when there was a rental car shortage and the cost to rent a car went through the roof? I do. It was a painful time for trip planning and it had an impact on our Little Rock plans. We dealt with the issue of sky-high rental car prices by not renting for the whole trip. Instead, we rented a car for the weekend and used that time to explore Hot Springs, Arkansas, drive to Crater of Diamonds State Park, and get groceries. It worked out well for us.

Lesson #10: Explore different modes of transportation.

We did not plan to rent and ride scooters in Little Rock. But we found ourselves in need of transportation and there were scooters available. So we hopped on and got on down the road. It was fun and something I would not mind trying again.

Lesson #11: Schedule time to play.

Since work is the priority (unlike a vacation), it may take some extra planning to make sure fun stuff happens around the work. R and I will often compare work schedules with the list of things we want to do to see what time will work best. We have been known to go do something fun in the morning (like visit the Little Rock Central High School National Historic Site) and work a little later simply because that fun thing is not open in the evening. It just takes a little extra planning.

Lesson #2 (again): Working remotely is a skill that takes practice.

It can be tough to fly somewhere new and jump right into work. One thing I learned from this trip is that doing something fun right off the bat is a good way to ease into a new location. After we arrived in Little Rock, R and I rented a car and headed to Hot Springs, Arkansas, for the weekend. We had a fun-filled weekend before returning the car, settling into our Airbnb and getting to work. It is not always possible to do something like this, but it is a good idea when you can.

Two friends on scooters in Litte Rock, Arkansas on a digital nomad journey
Giving scooters a try in Little Rock, Arkansas.

Working remotely from Nashville, Tennessee

Timing: one week in September

By the time this forth trip rolled around, I was feeling a little too confident in my abilities to plan a remote work trip and I had to relearn a bunch of lessons. Luckily, those lessons were balanced out by the good times that were had in Nashville and Kentucky.

Fun times that were had on my digital nomad journey to Nashville, Tennessee:

  • Exploring Germantown and eating dinner at Monell’s. Not only was the food delicious, but eating family style and getting to know the folks at our table was a lot of fun.
  • Seeing Lori Morgan at the Ryman Auditorium.
  • Catching a show at the Grand Ole Opry.
  • Hitting up Stones River National Battlefield because R loves herself a battlefield.
  • Shopping! I bought the cutest plaid cape to wear for Christmas in Paris.
  • Going on a cave tour at Mammoth Caves National Park.
  • Betting on some horses at Kentucky Downs. They race on grass!
  • Kayaking the Green River. Although I will say that this was a much slower activity than I was anticipating. I am used to Idaho rivers, and this was nothing like what I am used to.

Lessons I relearned working remotely from Nashville, Tennessee:

Lesson #1 (again): When you move locations on a work day, you are not going to get a lot of work done.

We decided to drive to Kentucky after work on Friday. It seemed like a good idea when we booked it, except we had to check out of our Airbnb by 10 a.m. That meant we had no place to work for the rest of the day. We found a coffee shop and did the best we could, but it was a challenge and not ideal.

Lesson #5 (again): Location, location, location.

Our place in Nashville was cute and located in a cute neighborhood. But it was a fair distance from downtown and it made exploring that area more difficult. We made do, but it involved a lot of driving and trying to find places to park.

Lesson #8 (again): When it comes to choosing a location to work from, think beyond the obvious.

For this trip, we picked our location based on two factors: the cost of a rental car and proximity to a national park. Almost everywhere we looked at in the U.S. had crazy expensive prices for car rentals. Nashville was an exception. It was also a reasonable drive to Mammoth Caves National Park (R is working on visiting every national park). So we made plans to work remote from Nashville and drive to Kentucky to do a little exploring.

Lesson #11 (again): Schedule time to play.

We did our best to do things like visit the cute little boutiques in the area on our lunch hours since they closed before our workday was done. We also took off work early a couple of days to enjoys things like a performance at the Grand Ole Opry. But overall, there did not feel like enough time to see everything we wanted to in Nashville.

The Opry stage in Nashville, Tennessee.
The Opry is a must when you are in Nashville.

Working remotely from Rome, Italy (my first international remote work trip)

Timing: one week in October

R cannot work outside of the U.S. so we mostly remain stateside. But I am allowed to work from almost anywhere. So when the price of a flight from Boise to Rome dropped to less than $500 (thanks Scott’s Cheap Flights), I jumped on it. A week is not a lot of time to spend in Europe, but I planned to stay in Rome for the whole week and try working. A week seemed good enough for this experiment. And it was!

Fun times that were had on my digital nomad journey to Rome:

  • Eating gelato every damn day. I would take a break from work around 7 or 8 p.m. and walk down the street to one of the local gelaterias (there were several). It was a daily highlight.
  • Learning to make pasta from scratch. The class started two hours late, but since I did not have a packed itinerary, I was able to make and enjoy my pasta at my leisure.
  • Touring the Colosseum, including the newly opened underground chambers. It was awesome.
  • Visiting Vatican City and touring the museums. I went on a Wednesday, which is when the Pope addresses the people. So the museums were not as packed as usual.
  • Going on a self-guided walking tour and wandering. It was my favorite thing about Rome. And pizza. That was also my favorite thing about Rome. Along with the gelato.
  • Experiencing Rome without all of the tourists. That is one thing I can thank the pandemic for.

Lessons I learned working remotely from Rome, Italy

Lesson #12: Do not hesitate to jump on a great opportunity.

Working remotely from Rome was an amazing experience and a highlight of my digital nomad journey. I am so glad I bought that plane ticket and gave working internationally a try. I probably will not do it a lot since R is not happy when I go on fun international trips without her, but it is nice to know I have the ability to work in other countries.

Lesson #13: Good wifi is crucial.

For the most part, the wifi at my Airbnb worked great. But then one evening it went down and it did not come back up. I started to work from my phone, which got the job done but was not ideal. After messaging the host, she got the wifi up and running again and I was back in business. Overall, it was not that big of a deal. But it made me realize that I was not quite as prepared as I could have been.

Lesson #14: If the trip is short, stay in one place.

Although it was really, really hard to stick to this one when all of Europe is just a train ride away, it was the right choice given the amount of time I had and the purpose of the trip. Plus, I did not feel rushed and I got to see and explore everything on my list.

Lesson #3 (again): Digital nomading is not cheap.

As much as I would love to galivant around the world, travel can be expensive. I did a lot of cooking in my flat, which helped. But between transportation, tours, souvenirs and gelato, I spent a pretty penny on my week in Rome. #worthit

Lesson #5 (again): Location, location, location.

I debated for a couple of weeks on where to stay. I found an adorable little Airbnb for a great price. However, it required a train ride to get into the city center. Another option I found was not as cute and a little more expensive, but the location was walkable to everywhere in the city. I finally decided on the place that was close but cost a bit more. It was the right decision. The place was not as cute, but it still had a lot of charm and the host was wonderful. Plus, it was worth paying a bit more to be in the right location.

Lesson #6 (again): Keep consistent hours, no matter where you are working.

Even in Rome, I stuck to Idaho office hours. This worked great for me. I would start work around 4 p.m. and wrap up at midnight. Then I would go to sleep until around 9 or 9:30 a.m. That gave me 5-6 hours to explore Rome. I got plenty of sleep, had plenty of time to explore, and I was still effective at work. This schedule may be a little difficult if you are a morning person, but I am a night person and it worked great for me.

Lesson #11 (again): Schedule time to play.

Do not be afraid to take time off to play. Yes, the point of this trip was to see if I could work internationally. But that does not mean I had to work the whole time. I took two days off (Monday and Friday) and worked three days (Tuesday, Wednesday and Thursday). It was a nice balance of vacation and work.

Colosseum tour on an international work trip to Rome.
Touring Rome during the day and working in the evening.

Becoming a digital nomad full time

Between the end of 2021 and the beginning of 2022, R’s and my housing situation in Boise changed. Basically, we did not have to move, but we needed to move. Because we did not have to move, that gave us time to pause and reflect on what we wanted to do. Like most big life decisions, it was hard to know what to do. Should I stay in Boise? Did I want to move? Did I want to buy a house? Because there were so many options available to me, I started to get overwhelmed and then I just quit thinking about it at all.

A conversation with my brother-in-law set me on this digital nomad journey fulltime. He mentioned how much fun it would be to live in a city, like San Francisco or New York, for just a couple of months. Not for forever, but just to see what it is like. I immediately agreed with him. That did sound like fun. And then it hit me: I could do exactly that! I did not need a permanent home base right now. I could live and work from lots of places. For the first time since I realized I needed to move, I was excited. And lucky for me, R is always up for an adventure.

Someday I may tell you all the steps we took next to become fulltime digital nomads. But the short story is: we sold a bunch of stuff, stored a bunch of stuff and drove R’s Subaru to Washington to begin a fulltime digital nomad journey.

Working remotely from Port Angeles, Washington (my first trip as a full-time digital nomad)

Timing: six weeks in January and February

The first “long-term” stint did not take a lot of adjustment or time to settle into. I think that had a lot to do with all of the short work trips we had taken previously. Working in Port Angeles, Washington, for an extended amount of time was fun. I enjoyed the relaxed pace a lot. We were able to see a ton of the Peninsula and explore at our leisure. There was not the usual sense of urgency and go, go, go. PA itself was cute and gritty. Looking back, January was probably not the smartest time to choose to live and work in this area. But it all worked out for us in the end.

Fun times that were had on my digital nomad journey to Port Angeles, Washington:

  • Spending quality time in Port Angeles. We visited the farmers market, ate at local restaurants, shopped at local shops and managed to snag an elusive Sasquatch donut. There was time to see and explore a lot.
  • Visiting all the beaches. Well, maybe not all of the beaches. But we visited a lot of them and each one was unique and fun. Second Beach ended up being my favorite. I also enjoyed finding agates and poppy jasper on Rialto Beach.
  • Hiking and nature walks to waterfalls, around Crescent Lake and up the Elwha River past the washout.
  • Exploring nearby towns like Sequim, Forks (yes, that Forks), and Port Townsend.

Lessons I learned working remotely from Port Angeles, Washington, for six weeks:

Lesson #15: Look for rentals that cater to longer stays.

Our first long-term Airbnb rental was awesome. The host had it dialed in. Everything from the labels to the pots and pans were just right for a six-week stay and it set the bar very high. Some rentals require a minimum stay of 30 days. This can be helpful when trying to identify good places that cater to longer stays.

Lesson #16: Pay attention to the weather.

This lesson was actually two-fold. First, driving to our location in January was awful! It took hours longer than it was supposed to because we ran into three different blizzards. It was stressful and scary. Not the best idea we have ever had and a good lesson learned on this digital nomad journey.

On the other hand, we lucked out when it came to weather the whole time we were living in PA. It was one of the driest Januarys on record and almost every weekend provided sunshine and light-jacket-only weather. I have so many fantastic beach photos and memories and I know that is not the usual for that time of year. So lucky us.

Lesson #17: You may get homesick.

I was not worried about working, since I had had a lot of practice at this point. And I was not worried about living somewhere new since I have moved a few times in my life. But this was the longest I had been away from Idaho and my family since college. I was worried I would miss my nieces and nephews. And I did.

Lesson #18: Pace yourself.

This trip to Port Angeles was sandwiched between two international vacations. There were just a couple of days between each trip and it was not enough. I need more time between trips, whether they be work or vacation. I need time to unpack, decompress, spend time with my friends and family, get a haircut, go to the dentist, etc. 

Lesson #4 (again): Things will not always go as planned.

My mom called me on my first day in PA and told me my brother-in-law had Covid. I had stayed at his house before driving to Washington. The next day I had symptoms and the day after that I tested positive for Covid. Thankfully, I had a mild case. But it was a pain trying to self-isolate from R in a small house and it was a real bummer not being able to explore or get groceries. Thankfully, R never got Covid even though we spent 10 hours in a car together.

girl on second beach on a sunny day
Second Beach explorations on a sunny winter day.

Working remotely from New Orleans, Louisiana

Timing: five weeks in April and May

New Orleans was an awesome place to spend five weeks. (Technically, Robbie spent five weeks there and I spent four. I had some appointments at home I had to come back a little early for.) The weather was darn-near perfect, although it did get a little hot towards the end of our stay. We had no idea when we chose New Orleans that April is festival season. What a delight! We knew the food was going to be good and it did not disappoint.

Fun times that were had on my digital nomad journey to New Orleans, Louisiana:

  • Eating all of the tasty, tasty food. We did our best to try as many different beignets as possible. We also ate our weight in cake from Rouses grocery store, because Rouses makes great cake. I will note that we were there during crawfish season, but since neither R nor I enjoy crawfish, it was wasted on us.
  • Living in a shotgun house in Mid-City. Our Airbnb was not great in a lot of ways, but it was quintessential New Orleans living in a great neighborhood.
  • Experiencing three days of JazzFest. This was really cool and a bit overwhelming. But we got to see a wide array of artists and eat a lot of really yummy food.
  • Enjoying the Easter parades. I do not have the words to explain this experience. Suffice it to say, it was unique.
  • Playing tourist when friends came to town.
  • Renting a car for the weekend and seeing a little more of Louisiana. We toured plantations, visited the Longfellow-Evangeline State Historic Site, toured the Tabasco Factory, and stumbled upon the Blues Festival in Baton Rouge. It was a great little road trip and weekend out of the city.

Lessons I learned working remotely from New Orleans, Louisiana:

Lesson #19: If you rent a bigger place and go somewhere cool, people may visit you.

We had guests twice in New Orleans. Technically, they are R’s people, but I enjoyed them nonetheless. Because of them, we went on tours and ate at restaurants we may not have on our own. It was fun to explore our “home” city with them.

Lesson #20: Take advantage of unexpected in-person work opportunities.

Ironically, one of the largest conferences and trade shows that my work participates in was in New Orleans while I was there. It was a great opportunity to network and see my teammates.

Lesson #21: Make sure the place has a washer.

We never gave much thought to a washer and dryer until we realized our place in New Orleans did not have one. I bought a portable washing machine/bag before we left and it did an okay job. But it was not a great replacement and R finally ended up a couple of blocks away at the laundromat. The inconvenience was enough that we always make sure our place has a washing machine these days.

Lesson #22: Gift certificates to local places make good gifts for digital nomads.

Friend and follow traveler, G, gifted R with some yoga classes at a yoga studio in New Orleans. R was able to walk to the studio each week and enjoy a session. This was a thoughtful and useful gift for someone who no longer lives in one place and has gotten rid of a lot of her stuff. It took some research on G’s part, but it was very much appreciated by R.

Lesson #2 (again): Working remotely is a skill that takes practice.

I had a very productive week the very first week in New Orleans. That was when I realized I had adapted to working from different locations and could be just as productive, maybe more, than when I am in the office. This was a big win on my digital nomad journey.

Lesson #9 (again): You do not have to rent a car for the whole trip.

There was no reason to have a car while in New Orleans. Public transportation treated us just right. But there were a couple of things we wanted to see outside of the city. Solution: rent a car for the weekend. It was affordable and allowed us to get out of the city for a weekend.

Lesson #10 (again): Explore different modes of transportation.

The public transportation system in New Orleans exceeded my expectations. That is probably because the Le Pass app was easy to use. The trolley stopped just a couple of blocks from our place and then it was about 20 minutes to downtown. The app was not always accurate, but it was easy to use and very affordable. I definitely recommend it in New Orleans.

Lesson #15 (again): Look for rentals that cater to longer stays.

This was not one of them. In fact, our New Orleans Airbnb may be the worst one we have stayed in as far as being equipped for long-term stays. I do not expect things like spices and baking supplies (although I appreciate them). But I do expect things like butter knives. There were no butter knives! We ended up going to the dollar store and purchasing typical kitchen items so that we could cook and eat for a month. It was a little ridiculous.

New Orleans trolley on my digital nomad journey
Heading to the quarter on the trolley.

Working remotely from San Antonio, Texas

Timing: two weeks in May

San Antonio is my favorite big city in Texas. This last work trip only confirmed that for me. I love the Riverwalk (north of downtown), the food, the music, the shopping, the vibe, etc. I do not love the weather a lot of the year and unfortunately, we experienced a heat wave during our visit. It was not lovely. But the fun times made up for the bad weather.

Fun times that were had on my digital nomad journey to San Antonio, Texas:

  • Living within walking distance to The Pearl. We could enjoy the farmers market on the weekend or get ice cream in the evenings.
  • Walking the Riverwalk north of downtown. The downtown section can be slow moving, especially on the weekends. But north of that area is always pleasant and made for nice evening strolls.
  • Shopping at Market Square.
  • Catching The Saga on the San Fernando Cathedral.
  • Road tripping to Luckenbach, Fredericksburg, and New Braunfels.
  • Enjoying live music at Sam’s Burger Joint and Gruene Hall.
  • Going to the top of the Tower of the Americas.
  • Being confused (again) by the Alamo. The site itself is a little underwhelming and if you dig into the history of the Alamo at all, you are going to be left scratching your head. But you’ve got to visit it when you are in San Antonio.

Lessons I learned working remotely from San Antonio, Texas:

Lesson #23: Two weeks can be fun, but it feels a little rushed.

I enjoyed the time we spent in San Antonio very much and I feel like we did a lot. But two weeks was not an ideal amount of time if you want to feel like you are living somewhere. I learned that I prefer longer stints.

Lesson #24: Take advantage of Little Free Libraries.

Although I have converted to an electronic reader (I currently have the Fire HD 8), R still prefers hardcopy. That presents a big challenge when you are nomadic. Enter Little Free Library. No membership is needed and these cute little libraries can be found all over. When you finish reading a book, you simply return it and grab another. The only disadvantage is the limited selection.

Lesson #9 (again): You do not have to rent a car for the whole trip.

We actually rented a car twice while we were in San Antonio. Once so that we could see a concert at Gruene Hall. But the second was because we had a whole day to kill with our luggage. Since storage options were limited, we opted to rent a car and go exploring. It was fairly affordable and a lot more fun than lugging around luggage in the heat and humidity.

Lesson #10 (again):  Explore different modes of transportation.

San Antonio has a public transportation app very similar to New Orleans. It is affordable and easy to use. And there was a bus stop less than a block from our house. It was very easy to get downtown and back and it was also very easy to get groceries. We could catch a bus, go to the grocery store and catch a bus back all in under an hour and for less than $2.

Lesson #16 (again): Pay attention to the weather.

This one was not entirely our fault. A heat wave went through the area and instead of May temperatures, we experienced summer temperatures. It was awful and only confirmed for me that although I enjoy visiting Texas, I do not want to live there.

Lesson #20 (again): Take advantage of work opportunities.

Ironically, there was another conference in San Antonio that my company was participating in while I was there. So I showed up and did some networking. But we also have an office in San Antonio. I decided to visit and although it is not a large office and plenty of folks were working remotely, I did get a chance to talk to a couple of engineers. It was a fun experience.

fish art on the San Antonio riverwalk
A fun and less-crowded part of the Riverwalk in San Antonio, Texas.

Working remotely in Philadelphia, Pennsylvania

Timing: two weeks in July

The point of this trip was to experience the 4th of July in a city on the east coast with a lot of history. Mission accomplished. There was so much to do and see and two weeks was not enough time. But we had a wonderful 4th of July and got to experience a tiny slice of what it is like to live and work in Philly.

Fun times that were had on my digital nomad journey to Philadelphia, Pennsylvania:

  • Celebrating the 4th of July! Philadelphia really treated us right with music from the Philly Pops, the parade, free entrance to various museums, a big concert, fireworks show and more.
  • Eating at the Terminal Reading Market. This unique place was located just a little over a block from our apartment which made it convenient for donuts and lunch.
  • Riding bikes from the city’s bike share program all over town.
  • Going to a Phillies game.
  • Eating cheese steaks. Obviously.
  • Experiencing the Chinese Lantern Festival.

Lesson I learned working remotely from Philadelphia, Pennsylvania:

Lesson #4 (again): Things will not always go as planned.

We worked hard to find the right place to stay in Philly. But three weeks before our trip, our Airbnb host canceled on us. The timing was especially awkward because we found out right as we were boarding a cruise to Alaska. So rather than relaxing and finding a bite to eat, we were looking for good reception so we could research and find a new place to stay. Thankfully, we were able to find another place and book it. But the whole experience was more stressful than I would have liked in general, and certainly more than I wanted the day I’m embarking on vacation.

Lesson #10 (again): Explore different modes of transportation.

Philly has an excellent bike share program and we rode all over the city. We got a monthly pass even though we were only there for two weeks since that was the most affordable option. It was a great experience.

Lesson #23 (again): Two weeks can be fun, but it feels a little rushed.

Two weeks is a little too short. It is better than nothing, but there was a lot to pack in and I was feeling a little exhausted at one point. I just wanted to relax, but that was tough to do because time was so limited.

Two girls on bikes in downtown Philadelphia.
Bikes are an excellent way to get around Philly.

Working remotely in Mackay, Idaho

Timing: four weeks in July and August

Idaho is a wonderful place to be in the summer, particularly the mountain areas. Mackay is a very small town located near Idaho’s highest mountain peak, Mount Borah. It is not located near anything else really. The town itself boasts a population of around 500 people. We actually stayed in an Airbnb about 6 miles south of town. It was country-living at its finest. I grew up in a small town very similar to Mackay, so I knew what I was getting myself into and I was excited to spend some time there and relax.

Fun times that were had on my digital nomad journey to Mackay, Idaho:

  • Exploring the great outdoors. I was especially happy to practice my terrible fly fishing skills.
  • Enjoying the local entertainment including the tractor driving competition and ranch rodeo. We were also fairly close to Challis, Idaho, where the annual Braun Brother Reunion takes place. So we were able to attend the concerts without having to camp.
  • Eating at every restaurant in town (there are just a handful).
  • Gazing at the stars. There is not a lot of light pollution in this area so the night skies are impressive.
  • Taking evening walks and enjoying the sunsets. They were impressive almost every night.
  • Observing two bull moose enjoying a snack in the field right at dusk.

Lessons learned working remotely from Mackay, Idaho:

Lesson #25: Digital nomading is easier with a car.

Having driven to two places and flown to three, I can say that having a car makes it easier to explore, buy groceries, etc. I still plan to fly to out of the way places, but I recognize that having a car makes life on the road a lot easier.

Lesson #26: Take pictures or a video of your abode when you first arrive.

I do not know about you, but we will often do a bit of rearranging when we get to a new place. It may be for comfort or it may be to set up a better work station. When it comes time to leave, there is a good chance you are not going to remember how things were originally arranged. A picture or a video will help you remember where everything goes.

Lesson #13 (again): Good wifi is crucial.

The internet in this rural location is good, when it is online. But it has a tendency to drop unexpectedly. After a couple of minutes, it goes back online and all is well. But that drop off can be frustrating when you are on a conference call. I came up with two workarounds:

  1. I started calling into important phone calls using both my computer and my cell phone. This way, if the internet dropped, I could still hear them and they could still hear me. It was a hassle, but it got the job done.
  2. I drove to our corporate headquarters, which is a couple hours away from Mackay, and stayed for a few days. I had an important presentation that I really needed the internet to not drop on. So I made the trek, enjoyed the Wood River Valley and saw some friends and coworkers.
Sunset in Idaho during a digital nomad journey
Summer sunsets in Idaho.

Conclusion (for now)

I do not know how long I will continue on this digital nomad journey. But I do know I am not tired of it and I have plans to continue to live and work from various places. The approach changes based on the lessons learned, but the fun times keep happening no matter where we go. 

Up next is Omaha, Nebraska, the Mississippi River (yep, you read the correctly) and Bend, Oregon.

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