What 2.5 Years on the Road Taught Me

May 7, 2026

I’ve always been a 7 on the Enneagram. For better or for worse, the kind of person who could never help but wonder what else was out there, was there something more? Even as a kid, I remember feeling restless. I had this deep sense of wonder and excitement for the world. I wanted to see the world, but more than that, I wanted to feel it, to experience it. I wanted to understand how other people lived, to be surprised, challenged, and changed by places and people completely unlike my own. I wanted to collect experiences, perspectives, and moments that would quietly reshape the way I saw the world.

I never really wanted a predictable life. Even when I tried to settle into the idea of conventional life, some part of me always felt like it was staring out the window, imagining another place, another version of myself, another way to live. I had big dreams, and somewhere deep down, I knew I was going to live them. While parts of this restlessness have been difficult, parts have also been beautiful – it’s what’s ultimately led me here, to where I am today – discovering the world the way I always dreamt.

The funny thing is, it didn’t happen the way I imagined. Up until 28, I had been fully immersed in the Silicon Valley tech startup life. My life revolved around work, and while I was passionate about what I did, somewhere in the back of my mind, I always knew that one day, I was going to quit my job and follow the open road. And 2.5 years ago, that’s exactly what life unexpectedly brought me. My job and I parted ways under difficult circumstances and what felt, at the time, incredibly destabilizing, ended up becoming one of the greatest gifts life has ever given me. What initially felt like loss, slowly revealed itself as serendipity – an opportunity to pursue the life I had always dreamt of, in ways I hadn’t thought possible at the time. So I packed everything into a backpack and did the thing I always dreamt of: I followed the open road, and let it take me wherever it wanted to go.

Since then, my life has unfolded in ways far beyond what I ever thought possible. I’ve chased endless sunsets from places I’d never heard of even days before, where daily sunset beers slowly turned strangers into little temporary families. I’ve jumped on buses, trains, and planes, on whims, just saying yes and trusting the road would lead me where I was meant to be. I’ve spent countless nights dancing barefoot on the beach with strangers who felt like lifelong friends for a night. I’ve felt so present, so alive, so full of love, so full of joy, that in so many moments, I’ve found myself looking around just trying to soak it all in, knowing it wouldn’t last forever. I’ve spontaneously jumped on crazy adventures with people I only met hours earlier, not knowing where we’d end up by nightfall. I’ve quietly spent New Year’s disconnected from the outside world at a silent meditation retreat while everyone else celebrated somewhere far away. So much of this life has been saying yes to the unknown – and that’s where I’ve always found the magic.

And somewhere along the way, I fell in love more times than I ever expected to in a lifetime.

I met someone who became the travel and adventure partner I had always dreamt of, and we spent four months exploring the world together the way I'd always imagined it – embracing the open road, immersing in the local culture, and seeing what adventure would bring us. It felt like the fulfillment of a lifelong dream. I met another person whose soul I deeply connected to, who saw beauty in life and love the same way I do, and we built a quiet, simple life together on a beautiful little island of the Philippines, something I never thought I would do. We shared slow mornings, blissful surf sessions, fresh coconuts on the side of the road, built a hostel, and cuddled away our rainy days in – a life that was so simple and so beautiful. I met someone else who brought back a childlike joy in me I hadn’t felt in a long, long time. Someone who I felt so light and easy and free with, and together we shared the biggest laughs and most peaceful stillness. And in between, there were so many other little moments of love, if even for a day.

There were so many surreal, beautiful, deep moments of love that I count myself as lucky for having gotten to experience. Traveling through foreign countries with people I had only just met, sharing deeply, our intimate little worlds together, the kinds of experiences people imagine when they think of honeymoons or great love stories. Riding scooters through tropical islands, embarking on the greatest adventures, endlessly discovering new places, waking up in cozy bungalows at the sea, making love until sunrise, laughing until we cried, becoming each other’s best friends in impossibly short amounts of time, feeling completely consumed by another person and the temporary little life we created together. But maybe because life on the road is so emotionally heightened, just like I’ve experienced so many moments of love, I’ve also experienced equal moments of heartache. So many intense connections that entered my life quickly and disappeared just as fast. And just like I’ve experienced more love than I ever thought I would, I’ve also cried alone on the streets and experienced more pain than I ever thought I would. But even those experiences taught me something about love, attachment, human pain, and myself.

One of the most meaningful parts of all of this has been the people along the way. You realize how quickly strangers can become family. Nobody cares about your job, where you live, what you own. People care about who you are – your character, your kindness, your values, your energy, your vibe. Sharing such intense, intimate experiences with people, brings about deep relationships quickly.

Along the way, I also made home in so many places. Volunteering at hostels for months at a time, meant living with people who slowly became some of my closest friends. There’s something weirdly intimate about building a life together so quickly — sharing bunk beds, late-night conversations, cheap dinners, heartbreaks, hangovers, inside jokes, and tiny everyday routines. Some of my favorite memories are from those chaotic months where we danced until 5 in the morning and then somehow dragged ourselves into our 7am shifts barely alive. There were so many moments where people I had only known for a short amount of time became my community — the people who shared my best memories and held me together through some of the hardest moments too.

This life has also allowed me to experience so many different kinds of environments. I’ve found quiet places around the world that made something inside me soften — places where life slowed down enough for me to realize how little I actually needed to feel happy. Slow morning coffees, scooters to the beach, a surf session under the sun, long dinners with friends, swimming in the ocean at sunset, making meaningful connections, waking up without rushing anywhere. I think travel showed me that there are a thousand different ways to live a meaningful life, and none of them are any more correct than another.

One of the most beautiful and important parts of all these years, has been seeing how differently people live all around the world. Different cultures, different values, different priorities, different means, different ways of thinking about work, family, love, community, happiness. Every place has their own distinct version of normal. While in Western civilization, we prioritize work, money, and individualism, many people lack a deep joy or simple contentedness. While in other countries where people have so little, children laugh on the streets, adults dance in the workplace, and community and family is celebrated.

I think that’s what I wanted to learn all along. That the world is so much bigger than the tiny lens we grow up with. That life is far more expansive than we’re taught to believe. It's made me softer, more curious, and certain that no version of life is more correct than another.

At times, it feels like I’ve lived a lifetime of experiences within these last few years. And I’m deeply grateful for it. I feel proud, like I’ve lived the life that my 15-year-old self dreamt of. But the strange thing about living your dream for long enough, is that eventually, even the dream becomes normal life. And normal life, no matter how beautiful, still has weight.

One of the biggest things this life has given me is resilience. Traveling long term sounds romantic — and in many ways it absolutely is — but it can also be exhausting, lonely, and confusing. You get sick in countries where you can’t communicate properly. You navigate unfamiliar systems completely alone all the time. You spend months immersed in languages you don’t understand. You go through heartache without anyone to help mend your tears. Things go wrong constantly, and there’s nobody there to fix them except you. But after enough years of this, something changes. You start trusting yourself differently. You realize you can handle anything life throws at you. You become someone who knows, deep down, that no matter what happens, you’ll figure it out. A friend I met a year into my trip and then saw again one year later, he said to me the second time around: “You look like you’ve seen it all. Like nothing really fazes you anymore.” And honestly, this is deeply how I feel.

One of the more ironic things about this life, is that freedom has a heaviness to it too. Everyone imagines freedom as purely exciting, but they don’t realize how mentally exhausting it can be to have endless choice, endless uncertainty, and endless space to think. Most people’s lives are structured for them. But when you live this way, there’s no structure unless you create it yourself. Some mornings I wake up and spend an hour thinking about my future, my purpose, where I should live, who I want to be, what kind of life would actually make me happy. Sometimes I miss the simplicity of just waking up, grabbing coffee, going to work, and not having the time to constantly analyze everything. Sometimes I envy people with routines, homes, and lives that feel grounded. And then other times, I know if I had lived a “normal life” all these years, I would’ve spent all that time daydreaming about the life I currently have.

Lately, I’ve felt exhausted in a way that’s hard to explain. Not physically, necessarily, but something deeper than that. Because while this life has given me freedom beyond what most people ever experience, it’s also asked a lot from me in return. There’s no stability in constantly moving. No solid ground. No permanent home base waiting for you at the end of the day. You’re always arriving somewhere and leaving somewhere else. And over time, I think that stretches you open, but also slowly wears you down.

Recently, I spent a month living in a co-living space in Taiwan surrounded by people living lives similar to mine – remote workers, freelancers, people who had intentionally stepped outside traditional paths. And what struck me most was not how different we were, but how similar we all were. We all loved our freedom, and were deeply proud of and grateful for the lives we had built. But underneath that, we all shared the same struggles. There was also loneliness, uncertainty, fatigue, and this quiet craving for groundedness. It made me realize that escaping conventional life doesn’t mean escaping struggle. It just means choosing a different set of struggles.

And then there’s the practical side of all this: money, sustainability. The constant question of how long this lifestyle can really last. In Asia, my life is pretty ideal. I’m able to work relatively little, live comfortably, and have enough time to actually enjoy my days. But when I think about going back to California or spending extended time in Europe, reality hits differently. Sometimes I wonder if I should just go back and get a “real” job again. Make more money, build something stable, stop thinking about finances all the time. But then I imagine giving up this freedom, and I feel this deep resistance inside me. Because even with all the exhaustion and uncertainty, there’s still something about this life that feels profoundly alive to me.

Lately, more than anything, I’ve been trying to learn how to let go a little. To loosen my grip on life and my expectations of it. To stop trying to perfectly optimize every decision, every future possibility, every version of life I could have. I’ve spent so much of my life in pursuit of something — meaningful experiences, happiness, becoming a better version of myself — and I think part of my own growth, is realizing there is no perfect answer waiting somewhere out there. Every door comes with beauty and loss. And maybe every path eventually becomes ordinary in its own way. I’m loosening my grip on paving my ideal life, and instead learning how to be at peace inside whichever I’m in.

Right now, I’m sitting in front of a waterfall while writing this, and I’m just trying to be here. Not worry so much about the future. Not wondering whether I’m doing things optimally. Just listening to the water, feeling the air, and existing for a moment exactly where I am.