I decided not to renew my lease in my apartment in December of 2021 in exchange for a life on the go. It’s been three years since that fateful decision and I have learned a great deal of life lessons along the way — some the hard way.

Today I will share with you some of those lessons. I had already by this point done a lot of traveling prior which gave me the confidence to set off into the world full-time. Even having visited all fifty states and three continents by the time December of 2021 rolled around, I had only but scratched the surface of understanding what it truly meant to live a “well-traveled” life. Nothing could have prepared me for what I would learn other than lived experience itself.

Lesson 1: The grass isn’t always greener on the other side

We’ve all heard the saying, “The grass is greener on the other side.” I prefer to rephrase it as “The grass isn’t always necessarily greener on the other side,” because it captures the nuance that no place is universally better or worse — it’s just different, and that perception is deeply personal. In some ways the grass may actually be greener, but that doesn’t mean it doesn’t also have its weeds. Life, after all, is too complex for sweeping generalizations. This lesson hit me hard as I set out on my journey, fueled by a mix of curiosity and a quiet hope to find Utopia and a place where I might finally feel a sense of belonging.

Growing up in the U.S., I’ve always felt a bit out of sync with the world around me. It wasn’t enough to be gay, but my interests, perspectives, and values even as a young boy often seemed to clash with those of the people I was surrounded by. As I got older, travel became my means of discovery. Not just of the world, but of myself and my potential “place” within it. I ventured to countries I admired from afar, searching for signs of warmth, and alignment with my values. What I found, however, was a more complicated truth: no place is perfect. Every country has qualities to admire and lessons to teach, but none are free of flaws. The dream of a utopia — a place that ticks every box and feels entirely like home — was just that: a dream.

The dichotomy of good and bad exists everywhere, in everyone, and in everything. Countries I had expected to love (and do) like Canada, Chile, and New Zealand offered aspects of life that resonated deeply with me, despite their own unique challenges. Meanwhile, places like Spain, Denmark, and Colombia — countries I that had also idealized — just didn’t ignite that spark I had thought they might. The reasons varied, from cultural mismatches to an intangible absence of a “home” feeling. These experiences forced me to confront my own rose-tinted ideas and reevaluate my expectations of what I sought in life. Ultimately, the “grass” may in fact be greener in some respects, but it comes with its own weeds and whether it’s worth it depends entirely on your perspective and priorities.

Travel didn’t reveal a singular answer or a perfect place. Instead, it gifted me with empathy and a nuanced view of the world — inclusive even of, albeit somewhat reluctantly, my home country, the U.S. While my travels didn’t cure my sense of disconnection, they helped me recognize that belonging isn’t solely about finding the “right” external environment. It’s an exceedingly subjective, layered experience, one that can’t be reduced to a checklist of pros and cons. Sometimes, the answer is far more metaphysical, and will always ultimately be imperfect. It’s worth evaluating your expectations realistically so you don’t wind up with a nasty case of Paris Syndrome.

Lesson 2: You can run, but you can’t hide

If you thought hopping on a plane would leave your troubles in the dust, think again! When I set out to explore the world, I unknowingly packed some extra baggage — of the emotional and mental variety. Like many, I had naively hoped that a change in scenery would magically resolve my inner struggles that have long caused discontent in my life. But as it turns out, wherever you go, there you are. The traumas, biases, and stresses that shape your life at home don’t simply vanish when your boarding pass is scanned.

I once heard someone say, “I tried traveling to escape myself, but it turns out I had just brought myself with me.” That sentiment socked me squarely in the gut when I realized that I too brought myself along with me. Whether you’re reeling from heartbreak, grieving a loss, or simply feeling discontented with life, those feelings don’t dissolve the moment you set foot in a new country. Compound those issues with the judgment and ugly beliefs people will sometimes have and project onto you because of where you come from, or what you look like, etc — it can be incredibly demoralizing. Despite what the glossy travel montages in movies or on Instagram suggest, life doesn’t pause for a scenic backdrop. On short vacations, you might feel a temporary sense of freedom and escape, but for long-term travelers, the merging of “travel life” and “real life” can make your internal struggles feel inescapable. 

For me, the challenge was finding balance: soaking in the wonder and joy of new experiences and living the life I had always dreamed of while managing the realities of life that persisted no matter where I went. When I left my apartment as an eager 26-year-old ready to explore the world, I didn’t leave behind my past experiences, identity, culture, fears, or insecurities. I brought them along — right alongside my suitcase. The key realization was that travel didn’t offer a clean slate or a miraculous escape, to start over and become someone anew; as I had hoped it would. Instead, it became a stage where my real-life challenges played out in unfamiliar settings. That’s not to say you shouldn’t chase your dreams of seeing the world; it’s simply a reminder that travel, like life, is layered and imperfect. It’s not about erasing your problems but being realistic about your expectations and learning healthy coping mechanisms for when the going gets tough so it doesn’t weigh you down. 

Lesson 3: Slow and steady wins the race

Embody the turtle, not the hare. Or don’t — but don’t say I didn’t warn you.

Not everyone travels at the same pace, and that’s perfectly fine. But when it comes to long-term travel, slowing down can be key to sustainability. When I first started traveling full-time, I dove in headfirst, eager to experience everything. South America was (and still is) so full of wonder for me, and I approached it with unbridled enthusiasm, determined to see and do as much as possible while juggling a full-time job.

It didn’t take long for burnout to rear its ugly head. Within my first month, I had hopped through four countries, come down with COVID-19, followed by a mean case of food poisoning, all the while keeping up with work, exploring when I was healthy, and navigating everyday life. By the end of it, I was thrashed — and there was still so much more ahead! A harsh wake-up call.

The devil is truly in the details. Even just a presumably short one hour flight is never just a one hour endeavor. There’s the packing, getting ready, arriving at the airport two hours ahead of take off, checking in bags, shuffling through lines and navigating security, the actual flight itself (plus any delays), deplaning, if you’re on an international flight — passport control and customs. Then transit time to your new accommodations, assuming it’s ready for check-in. In total what appears to be just a one hour event ends up being more like a four-five hour exploit of your time and patience. Beyond just travel time, a packed itinerary doesn’t account for the curveballs like illness, jet lag, or the mundane tasks of “adulting” that follow you wherever you go, and this is a big one — rest. While the idea of doing nothing might feel counterintuitive to the spirit of travel, it’s essential for keeping those spirits high and you in one piece.

For digital nomads especially, the logistics of daily life demand more time than a vacation mindset allows. Balancing work, rest, exercise, and socializing is just as important as exploring your new surroundings. Grocery runs and cooking save money and keep you healthy but take time. Socializing combats loneliness but requires effort and you guessed it — time. Sightseeing, while thrilling and likely your motivator for being a nomad in the first place, needs to be balanced with time to recover, recharge, and sometimes to just simply do nothing. You’re not doing yourself or your sanity any favors by being ‘always on’.

Through trial and error, I discovered that doubling the time I’d usually spend in a destination on vacation makes a big difference. For me, that more than likely means two weeks minimum for a single city and at least a month for countries with a couple stops. For example, when I visited Chile, I focused on the regions that called most to me — Araucanía and Magallanes y Antártica Chilena in Patagonia. I spent at least two weeks in each general area and padded my trip with extra time for the capital and other transition points. In total, I stayed just shy of two months in Chile, and while that may sound excessive, it struck the perfect balance for me given the kind of experiences I wanted to have there and how high it was on my list of places to see.

Everyone’s priorities and travel styles are different, but I’d urge you to give yourself more time than you think you need. Slowing down doesn’t mean sacrificing adventure — it means prioritizing and creating space to truly experience a place, work, rest, and embrace the unpredictability of life on the move. Finding your rhythm is a deeply personal journey, but trust me, the turtle’s pace is worth considering.

Lesson 4: Prepare for the worst, but hope for the best

Proper planning is the cornerstone of success for anyone embracing the Digital Nomad lifestyle. If you’re not a Project Manager already, you will be one after some time on the go. From mapping out destinations to managing logistics, the nomadic journey demands meticulous preparation. Balancing factors such as personal interests, budget, accommodation, transportation, safety, internet reliability, travel requirements (like visas), and any other essentials is no small feat. While the challenge is exhilarating, it requires a level of foresight and adaptability that can make or break your experience.

Having a comprehensive travel plan, along with contingency strategies, is essential because no amount of research can fully predict the realities of a new destination – risk management becomes a critical skill. To illustrate this, I’ll take you on a little trip back in time to South America (again). This time to Puerto Iguazú, Argentina. The plan was to spend a week soaking in the grandeur of Iguazú Falls and take in the lush surroundings. Our Airbnb hosts were extraordinarily sweet, the weekend was idyllic. Saturday morning we arrived, explored the town and took a little excursion into Paraguay; we hit the falls on Sunday. However, when Monday brought the workweek, unreliable Wi-Fi and failing mobile hotspots derailed our plans. Despite our attempts to reset/move the router and our backup measures, the internet connectivity had proven to be unsustainable, forcing us to cut our stay short and retreat to Buenos Aires – of course driving up expenses. 

This served as a tough lesson in the importance of thorough research and realistic expectations. We hadn’t accounted for the weaker internet infrastructure in Argentina outside of Buenos Aires (at least at the time), which ultimately led us to cancel other destinations in the country like Ushuaia and Bariloche to avoid further complications. This was a major disappointment. Setbacks like this really underscore the value of thorough research and adaptability. The key is prevention. Life will always find a way to throw a wrench in your plans, but you’ll greatly reduce the type of fall from grace I experienced in Argentina by not making any assumptions about basic essentials such as internet connectivity, and exercising your due diligence to ensure all your needs are met.

Lesson 5: You know nothing and you never will. And if you think you do – you don’t.

Reading that probably feels a bit like a blow to your ego — and perhaps it is, but hear me out.

“When in Rome, do as the Romans do” is a phrase often touted as travel wisdom, but it carries an underlying assumption: that we know what it means to be a Roman — or otherwise, for that matter. The truth is, no one can fully understand a group of people as a collective, not even their own. Yet we so often have such strong opinions and ideas about what it means to be from somewhere. What it means to be American, Japanese, Russian, or Indian. Our perceptions of places and cultures are often based on fragmented ideas drawn from media, history, or fleeting personal experiences, all of which are limited in scope, and perpetually outdated. The world is vast, diverse, and in constant flux, making it impossible to truly know a place or its people in any definitive way.

Consider how rapidly the world changes. The highly romanticized Paris during Les Années Folles is a different city from today’s Paris, just as the China of the 1980s contrasts sharply with its current urban megacities. Even just the span of a few years can bring about great change in this modern era — the United States for example is certainly not the same place today as it was in 2015, or even just 4 years ago. Borders fall and shift while political consequences ebb and flow. Languages change and evolve while cultures blend and intermingle, ensuring that no one time or place remains static. Our collective understanding of a destination, whether shaped by movies, books, or personal experiences, is inherently flawed, one-dimensional, and fleeting — what is true for some today is not for others, and may no longer be true at all for anyone tomorrow.

Rather than clinging to preconceived notions, stereotypes, and statistical snapshots like we as human beings so often do, we’re better served by approaching the world with curiosity and humility. People are highly variable, even within single cultures. Letting go of rigid ideas so as to allow us to experience a place for what it truly is in the present moment, rather than what we expect it or want it to be. Travel becomes a more rewarding and transformative experience when we embrace the reality that we all generally know very little, and can never fully know anything about anyone from anywhere. This openness not only shields us from disappointment but also enriches our journey, offering a rare chance to witness the evolving story of a culture or place in a way that is unique to the moment we find ourselves in. Time marches on, and with it, change is inevitable — embrace it and stay humble.

Conclusion

In the end, the life of a digital nomad is one of constant learning and adapting. This is what we signed up for afterall, right? The past three years have shown me that the journey and the destination both are far more than what meets the eye. While I’ve learned to embrace imperfection and navigate life’s uncertainties, I’ve also realized that the true beauty of this lifestyle sometimes lies in its surprises. Whether you’re contemplating your own leap into the nomadic life or simply seeking inspiration, remember that every adventure, big or small, teaches us something about the world and our place in it. Here’s to embracing the lessons, one step (or one flight) at a time.