The road taught us what no postcard ever could: you can’t outrun real life, even with a one-way ticket.
When my ex-girlfriend Emma and I sold our Brooklyn apartment and most of what we owned to travel indefinitely, we felt like we'd cracked some secret code. Everyone else was stuck in the grind while we'd be sipping coffee in Lisbon, working from Bali, living the dream.
Six months later, we were back. Not because we ran out of money or had some dramatic breakup (that came later). We came back because the fantasy and the reality were two completely different things. Here's what actually happened when we tried to escape everything.
1. The "location independence" myth hit different
Remote work sounds amazing until you're troubleshooting Zoom calls at 3 AM because your client is in New York and you're in Thailand.
Nobody mentions that "work from anywhere" often becomes "work from everywhere, all the time." We'd be at a beautiful beach, and I'd be refreshing Slack. Emma would be editing photos in a cafe in Morocco while fielding emails about a project that couldn't wait.
The boundaries we were supposedly escaping? They just became more blurred. At least in Brooklyn, I could leave the office.
2. Minimalism looked better on Instagram
Before we left, we did the whole Marie Kondo thing. Does this spark joy? If not, sell it. We were ruthless. Down to two backpacks each, proud of ourselves for being so enlightened.
What nobody tells you: constantly replacing basic things you need gets expensive and exhausting. Need a proper kitchen knife? Buy one, use it for a month, give it away. Need a decent pillow because the hostel one is basically a sack of rocks? Same cycle.
The minimalist aesthetic is beautiful until you realize you're just creating waste with extra steps.
3. Community isn't something you can Airbnb
I'm an introvert—I figured I'd be fine with surface-level connections and moving on every few weeks. Turns out, humans are wired for belonging, and transient relationships hit different when they're all you have.
You meet amazing people in hostels, have deep conversations, exchange Instagrams, and then... nothing. Everyone's always leaving. Including you. Emma and I started having the same conversation with new people every few days. Where are you from? How long are you traveling? It started feeling like Groundhog Day with different accents.
Meanwhile, my friends back home were deepening their relationships, showing up for each other's hard moments. We were collecting acquaintances.
4. Decision fatigue became the actual job
Every few days, we had to figure out: Where next? How do we get there? Where do we stay? Is it safe? What's the visa situation? Can we find reliable WiFi?
The mental load of constant decision-making is real. What started as freedom became its own kind of exhausting routine. Emma and I were spending hours every week just on logistics. Planning the next move. Researching. Booking. Adapting when things inevitably fell through.
I remember sitting in a cafe in Lisbon, spending my entire afternoon trying to figure out our next three stops, thinking: "Is this really what I quit my stable life for?"
5. The relationship couldn't hide behind routine anymore
Here's the thing nobody mentions about traveling as a couple: you're together constantly. Not "come home after work and watch TV together" together. Twenty-four hours a day together.
Emma and I had been fine in New York because we had our separate routines, our own friends, our different spaces. On the road, we were each other's everything—social life, coworker, roommate, entertainment. Turns out we'd been using our busy lives to avoid noticing we'd grown apart.
Without the buffer of normal life, every incompatibility became obvious. She wanted to party in hostels. I wanted quiet guesthouses. We broke up two months after getting back, but honestly, the relationship ended somewhere between Vietnam and Cambodia.
6. "Finding yourself" is mostly just... boredom
The spiritual awakening I was expecting? Didn't happen. Instead, I spent a lot of time just... waiting. Waiting for buses. Waiting in airports. Waiting for the next thing to feel meaningful.
Social media makes travel look like one peak experience after another. The reality is mostly mundane moments punctuated by occasional "wow" instances that you then spend 45 minutes trying to photograph correctly. I did learn things about myself, sure. But I could've learned them faster and cheaper through therapy.
The geographic distance didn't create the psychological distance I thought it would. Wherever you go, there you are—and apparently, I'm someone who likes structure, routine, and a drawer full of matching socks.
7. The privilege guilt got heavier
This one's uncomfortable but needs saying. We were traveling through places where people earned in a month what we'd spend on a nice dinner. The economic disparities you can intellectually understand from afar become visceral when you're living them.
Emma and I would be complaining about slow WiFi while watching people work construction jobs in extreme heat for wages we couldn't fathom. We'd haggle over price differences that meant nothing to us but might mean everything to a street vendor.
The "finding ourselves" narrative started feeling embarrassingly self-indulgent. We weren't doing anything meaningful. We were just consuming experiences in different locations.
Final thoughts
Coming back felt like failure at first. We'd made this big dramatic exit, told everyone we were done with conventional life. Having to admit it didn't work out was humbling.
But here's what I actually learned: the life you're running from is usually the life you need to fix, not flee. Geography doesn't solve internal problems. The "digital nomad" lifestyle works for some people, genuinely, but it's not the automatic upgrade the Instagram posts suggest.
I'm back in a one-bedroom in Queens now. I have a drawer full of matching socks. I see my friends regularly. I have a favorite coffee shop where they know my order. And honestly? I'm happier than I was in any of the "paradise" locations we visited. Turns out roots aren't a prison—they're just what happens when you stop running long enough to actually grow.
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