What you need to know about working and traveling – my lessons learned from 18 months on the road

Thinking about trying life on the road? I couldn’t recommend it more! If you are one of those lucky remote workers, why not dip your toes into a nomadic lifestyle while keeping your day job? This is the perfect opportunity to experiment with a new kind of lifestyle with minimal risk. Even if you do not foresee a future as a lifelong nomad, experiencing extended time away from the monotony of day-to-day life has a litany of positive effects. Why not try working and traveling for just a few months?

Whether you are ready to hit the road tomorrow or are just fantasizing, I am excited to share my greatest lessons from the last 18 months on the road.

1. A newfound sense of urgency to experience the world

Working and traveling - Great Falls, Montana
Great Falls, Montana

At the beginning of my travels, I moved from place to place every 4 weeks. As a full-time remote worker, that only gave me 2 full weekends that were not bookended by travel to and from another destination. This meant using all of my spare time to see and do as much as I possibly could. I began to feel a new sense of urgency to explore and became hyper-aware that each moment was truly fleeting. 

2. It’s possible for a cat to become your best friend 

I’ve been unapologetically in love with my cat since we first met. However, traveling together has brought our relationship to a whole other level. There is something really special about being the only constant in each other’s lives. This kind of experience is sure to strengthen an already strong bond between a pet and their human. 

3. Working and traveling is hard on clothing – leave your favorite items in storage

Definitely a less intuitive piece of advice, it’s best to pack clothing that you are not too attached to. The reason is that traveling full-time will take a massive beating on your clothes. Between wearing the same thing more often than normal and the range in quality of laundry facilities that you will surely encounter, your clothes will wear and tear at an alarmingly fast pace. And, even if your clothes are immune to the stress of travel, you will also get sick of them. I found that I prefer to cycle out old clothing and replace it with something new every few months. 

4. The value of being minimalistic 

While we are on the subject of stuff, becoming truly minimalistic has been one of my favorite lessons. Having fancied myself as “lean” with stuff in a previous life, traveling full-time has really pushed my limits. I am currently using a system where I allow myself three trips from the car each time I move. Anything more than that starts to encroach on the joy of the journey. I suggest thinking about the number of personal belongings you are willing to deal with before embarking on your journey. Don’t your experience of a new destination be dampened because you are already dreading moving to the next one.

5. Acceptance of new environments

Working and traveling - Anchorage, Alaska
Anchorage, Alaska

Another important lesson is that you are truly at the mercy of other people, especially your hosts. Since you will be booking most housing sight unseen, you will inevitably run into living situations that are not up to the same standards as your personal home. The good news is that you can always make minor modifications to increase your comfort level. If I can save $1000 a month by booking a lower-end Airbnb, why not spend $100 to spruce it up? Instead of worrying about the mess in the fridge or the lack of dish towels, I simply clean it up and make a trip to the Dollar Store. Problem solved.

6. While working and traveling, always arrive on a Saturday 

Speaking of the inevitable surprises in housing, when checking into new housing it’s also helpful to arrive on a Saturday. Assuming you work Monday through Friday, like me, this will allow you a full day to troubleshoot issues with the internet, do some extra cleaning, buy groceries, and make a Target run for any needed items. 

7. Being prepared with a backup plan for the Internet 

Since I rely on the Internet to do my job, I had to mitigate the risk of increased outages. In fact, one of the most frustrating aspects of working and traveling is that you often have to share internet access with your host. This may mean limited (or no) access to the router. In this case, I always ask the host the best way to handle an outage.

I also upgraded my Verizon plan to include 25 GB of mobile hotspot data and carry a Verizon Jetpack, which is a small piece of hardware that provides an additional 150 GB of data per month. So far I have not activated my device, but carrying it around gives me a sense of security that is worth the investment. I do, however, use my mobile hotspot data fairly consistently. 

8. A new level of self-expression

The pressure of fitting in during regular day-to-day life had been more stifling than I could ever imagine. Once I left my home in Los Angeles, CA, I felt freer to dress the way I wanted to. Additionally, cycling through a small set of clothing every few months also allowed me to experiment with new looks without too much commitment. There is something about true anonymity that is surprisingly empowering. 

9. Working and traveling can be heart-wrenchingly lonely (and that’s okay!)

Tucson, Arizona

For some reason, loneliness never occurred to me as a potential hurdle in working and traveling. So, when it hit me, it hit hard. But, powering through the long stints with little interaction with close friends and family taught me an important lesson. In a sense, I finally became comfortable with who I am. I found this to be the most unexpected benefit of long-term travel.

10. The value of connecting with different kinds of people 

A combination of becoming more secure with myself and an extended life on the road also taught me to appreciate other people for exactly who they are. Once you leave your bubble it can be shocking to run into people who speak differently, have opposing political views, or simply don’t like you. It took a while, but I eventually learned to accept this and find connections wherever possible. 

11. New hobbies are extra fulfilling while working and traveling  

Even though I am constantly trying to see everything as fast as possible, I still end up with more spare time in the evenings than I was expecting. Getting out of your daily grind is the perfect time to start a new hobby. I took up blogging to fill the extra time!

12. Healthy habits must be nurtured during extended travel

It’s no surprise that traveling makes it easy to go into perpetual vacation mode and ignore your healthy habits. In order to prevent this, I use an app called HabitShare to hold myself accountable for my goals for my diet, exercise, and meditation. Traveling is a good time to focus on maintenance while still leaving space to experience new things. As with everything in life, discipline and freedom are a delicate balance.

13. Set up local safety alerts before they are needed

Lincoln, Montana

One thing I learned the hard way was to opt into local emergency alerts before moving to a new destination. Upon arrival to Rapid City, SD last spring, a wildfire came dangerously close to my end of town. Unfortunately, I had not researched the local emergency alert systems, so I had no idea if my housing was affected. Flustered, I spent nearly an hour trying to figure out what to do. Luckily I did not need to evacuate, but in a real emergency, I would have been wasting valuable time. These days I use a mobile app by Everbridge to manage my alerts.

14. Perform car service early and often

This may seem obvious, but it’s easy to forget if you are like me and rely on the service light. While this method may work when you live 5 miles from the dealer, when you are 500 miles from the next large town, you need to be a little more careful. I suggest adding this to your departure checklist and always going in early for your next service appointment. When living on a perpetual road trip, your car is your lifeline.

15. Boundaries are meant to be pushed

Finally, the biggest benefit of traveling for extended periods of time is shaking yourself loose from the comfort zone that you may not even know you are in. Take the time to feel scared, uncomfortable, lonely, and lost. Do not immediately retreat into a new comfort zone. Extended travel is the time to push your boundaries. And the reward will be personal growth beyond what you thought was possible. 

White Sands, New Mexico

Conclusion on working and traveling

While these are some of the most important lessons that I have learned, everyone’s path will be different. The beautiful thing about travel is that it tends to reveal exactly what you are ready to see.

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