Lessons from five years on the road

Five years is a pretty long time. In that span, you could pursue a JD/MBA, witness a child's journey through kindergarten, or even write a couple of books. During the past five years, I have experienced more of the world than I ever thought possible in a lifetime. I've started businesses, formed enduring friendships, improved my fitness, and truly lived life. The lessons I've learned during this time are countless, but there are a few that stand out, and these are likely to shape the rest of my life, whatever form it may take.


You don't need a lot of stuff.

My storage unit is filled with boxes. I do not have an accurate inventory of what is inside them but I suspect that more than half contain clothes. Button-down shirts by the dozen, fancy cashmere sweaters, expensive shoes. I have not seen or worn any of these in the past 5 years. I've traveled with 6 everyday tee shirts and a sweatshirt or 2 in addition to the basics like socks underwear and shorts. Everything fits in a 60 liter Osprey backpack. Although I would make use of the clothes in storage if I had access to them, I have come to realize that I don't need them. In fact, I suspect that when the time comes to empty the storage unit one way or another, the majority of it will be donated or tossed out. Think about what you really need in life and prioritize what matters: friends, family, new experiences, and personal growth.

Hardship can create the fondest memories.

When I look back on the times and places I've come to hold most dear, I distinctly remember that many of them were rife with challenges. In africa, we struggled to find reliable wifi. Renting an apartment near the beach in Zanzibar was a great idea, until we found ourselves watching the owners remove tree branches with a machete in an attempt to strengthen the signal of their over-the-airwaves-based internet. On the walk to Macchu Picchu, it was freezing at night (and there was a lot of walking). I remember being so cold that I couldn't fall asleep. Remembering these experiences now brings a smile to my face. Despite slow internet speeds, the beach was spectacular. Seeing the sun rise over the mountaintops and hit those ancient stones made every frigid step worthwhile.

Anywhere can feel like home.

Over the course of our travels, we have stayed in more than 100 Airbnbs and have learned how to make any place feel like home. Ultimately, being with the person or people you love is what truly creates a sense of home. If you are safe and comfortable and can get a good nights sleep and prepare meals, there is not much else that constitutes basic needs. Add in a family photo or 2. Organize the closet so you can access your wardrobe. Spread out the items you need in the bathroom. There is much to be said about having a space that is your own, that becomes a part of you over time, that you could navigate in the dark with your eyes closed. What I've learned is that you can create a small sense of that with you wherever you go.

Shared experiences forge meaningful friendships.

We've been fortunate to have forged some lasting relationships during our time traveling. There is something about having a shared vocabulary and experience that brings people together. I imagine this is why people with children of similar ages often become friends: you immediately relate because you are going through the same stage in life and can converse in a meaningful way about the joys and challenges of that experience. Choosing to forego a stable home for a nomadic existence is an uncommon path, especially prior to COVID. When you come across others who have made the same choice, there is an instant connection, an intuitive understanding that there is more out there than we've been led to believe. Even if you do not have much else in common, this baseline consensus provides a solid foundation for friendship. When you pair that with experiences and adventures that are out of the ordinary, truly powerful bonds can be formed in short periods of time.

You can be productive from anywhere.

When we set out to travel, I made a commitment that I would prioritize work in the same way I would if I had continued showing up at an office each day. While I quickly found myself far more productive without the distractions of the typical office environment, it was not without challenges. Shared coworking spaces require you to set up and break down each day, effectively limiting the number of "things" on ones desk. This constraint highlights the importance of optimizing such gear to maximize productivity. Mouse, keyboard, laptop stand, extended display, noise-cancelling headphones. This requires some trial and error, but once you land on an ideal setup, you'll know. There is also a level of focus that is required - and further developed - to effectively work from somewhere other than a quiet space of your own. Coffee shops and WeWorks are rife with distractions, but once you've developed the ability to block those out and focus on the screen in front of you, that is a skillset that translates elsewhere.

If you make use of your time, you will (seemingly) have more of it.

I have written before about my fascination with how humans perceive time. The example I use to set the stage is a week-long vacation whereby the first half is spent sitting on a beach napping and reading and relaxing and the second half is filled with activities, sightseeing, nonstop movement. I think we've all experienced both of these scenarios and for me at least, the former is over in an instant. When I look back, as blissful as those days may have been, time flew by quickly. On the other hand, while it may have been somewhat exhausting, those days that were filled with activities seemed to be longer. This isn't to say one is better than the other. All of us certainly need time where we are effectively doing nothing, and ideally thinking about nothing. However, when you zoom out and think about the scope of a lifetime, it seems to reason that one filled with adventures, different chapters, various hobbies, experiences in novel environments will feel larger and more satisfying on the whole.


If you had told me five years ago that I would be effectively homeless, having traveled to over 30 countries, started businesses and made lifelong friends, I would have thought you were crazy. It's amazing what can happen when you do scary things. One seemingly crazy decision leads to countless small decisions which ultimately lead to real growth. Find that growth for yourself, whatever your life might look like. Think about what you could learn, who you could be, 5 years from now.

Bart Boughton