The backpack weighed eleven kilograms. I know this because I weighed it obsessively for the first three weeks, convinced I could shave another kilogram if I just found the right merino wool shirt or switched to a lighter pair of shoes.
This was 2019. I was twenty-four, between things in the way that people in their twenties describe it — which is a polite way of saying I had no fixed plan, a modest savings account, and the kind of restlessness that can only be cured by movement.
I bought a 40-liter Osprey Farpoint. I packed what I thought was the minimum viable wardrobe. I flew to Bangkok. And for the next twelve months, everything I owned was on my back.
The Packing Philosophy
Here is what I carried, because everyone asks and because the list reveals more about psychology than logistics.
Three t-shirts. One long-sleeve shirt that could pass as “nice” if I rolled the sleeves. Two pairs of shorts. One pair of lightweight pants. Seven pairs of underwear and socks — the only item I didn’t try to minimize, because laundry in transit is an unreliable art. One rain jacket. One pair of walking shoes that looked enough like normal shoes to get me into restaurants. One pair of flip-flops.
A laptop. A Kindle. A phone. Charging cables. A small first-aid kit. A microfiber towel. A headlamp. A padlock.
That was it.
The first thing you learn about long-term packing is that you’ve packed too much. By week two, I had mailed a shirt and a pair of shorts back home from a post office in Chiang Mai. By month two, I’d lost one pair of socks and didn’t replace it because I genuinely could not justify the weight.
This sounds absurd written down. It was absurd. But there’s something that happens to your brain when every physical possession has to be justified by its weight-to-utility ratio. You start seeing everything through that lens. Not just what’s in your bag, but what’s in your life.
The Route
Bangkok to Chiang Mai. Chiang Mai to Luang Prabang. Laos to Hanoi, down the coast of Vietnam. Cambodia. Back to Bangkok. Down to the islands. Over to Myanmar, which was still open to tourists then. Nepal. India — Rajasthan, Varanasi, Kerala. Sri Lanka. Then west: Turkey, Georgia, a brief stop in Armenia. Down through Jordan. Morocco.
It wasn’t a straight line. It was more like a weather pattern — following the climate, the visa rules, the recommendations of other travelers, and occasionally my own curiosity to places nobody had suggested.
I spent anywhere from three days to six weeks in each place. The length of stay was usually determined by one factor: how much the place surprised me. If I arrived and it was roughly what I expected, I moved on quickly. If it defied my expectations — if it was stranger, more beautiful, more uncomfortable than I’d imagined — I stayed.
This is why I spent three days in a popular Thai island (exactly as advertised: beautiful, expensive, crowded) and six weeks in a small town in northern Laos that isn’t in any guidebook, where I rented a room above a noodle shop for $4 a night and spent my days reading, walking, and having halting conversations with a family who spoke almost no English and found my existence endlessly amusing.
The Freedom Part
The freedom is real. I want to be clear about that, because the next section is about the parts that aren’t in the Instagram posts, and I don’t want the honest parts to overshadow the transformative ones.
Waking up in Hanoi at six in the morning, stepping over the threshold of a guesthouse into a street already alive with vendors and motorbikes and the smell of pho from three different directions. The knowledge that I could stay here or leave today, that nothing anchored me to any specific place, that the only deadline was my visa expiration.
Sitting on a rooftop in Jaipur at sunset, watching the Pink City turn gold, and deciding in that moment that I would go to Varanasi next because a German backpacker at dinner the night before had said, “It will ruin you in the best possible way,” and that seemed like a good enough reason.
Taking an overnight bus in Myanmar from Mandalay to Bagan, arriving at dawn, renting an electric bicycle, and spending the entire day riding between two thousand temples spread across a dusty plain, without a plan, without a guide, without anyone knowing or caring where I was.
That kind of freedom rewires something in your brain. Not permanently — the rewiring fades when you return to routine. But for the duration, you experience a version of yourself that isn’t organized around obligations, schedules, or expectations. You find out what you do when you have nothing you have to do.
What I did, mostly, was walk. Read. Write. Talk to strangers. Eat things I’d never eaten. Get lost on purpose. Sit still in places that rewarded sitting still.
The Loneliness Part
Now the other side.
Long-term solo travel is lonely in a way that’s hard to describe to people who haven’t done it. Not lonely like “I’m alone tonight.” Lonely like “I’ve had meaningful conversations with forty people this month and none of them will remember my name in a year.”
The social life of backpacking is intense and shallow. You meet someone in a hostel common room. You have a four-hour conversation about your life, your dreams, your fears — the kind of conversation that takes years to reach in normal friendships but happens in hours when both people know they’ll never see each other again. It’s intimate and it’s disposable. You exchange Instagram handles. You say “let’s meet up in [future city].” You almost never do.
By month five, I was genuinely tired of introducing myself. Tired of the same getting-to-know-you script. Where are you from. Where have you been. Where are you going next. How long have you been traveling. The questions are reasonable and the conversations are often good, but the repetition creates a strange existential fatigue. You start to wonder if you’re a person or a routine.
I spent a week in a guesthouse in Kochi, India, mostly alone. I read four books. I ate the same meal at the same restaurant every evening — fish curry, rice, a lime soda. The restaurant owner, after three days, stopped asking what I wanted and just brought it. That small act of being known — of someone recognizing my pattern and anticipating my needs — nearly made me cry, which tells you something about how deprived of continuity I’d become.
What You Learn About Need
The most lasting effect of living out of a backpack isn’t the travel stories. It’s the recalibration of what you think you need.
Before I left, I lived in an apartment with a closet full of clothes, a kitchen full of appliances, a shelf full of books, a desk full of gadgets. Normal stuff. The accumulated possessions of a normal life.
After twelve months of having nothing, I came home and looked at all of it with alien eyes. Why did I own eleven t-shirts when I’d just spent a year proving that three was sufficient? Why did I have a blender, a food processor, and a stand mixer when I’d eaten better meals from street carts than I’d ever cooked at home?
This isn’t about minimalism as an aesthetic. I’m not going to tell you to throw everything away and live out of a capsule wardrobe. The insight is subtler than that.
What long-term backpacking taught me is the difference between need and default. Most of what we own, we own by default. We acquired it at some point, for some reason, and it’s still there because getting rid of it requires more effort than keeping it. We don’t need it. We just haven’t made the decision to not need it.
The backpack forces the decision. Every item is a conscious choice. And when you live with only conscious choices for long enough, you start to see the unconscious defaults everywhere — not just in your possessions, but in your habits, your relationships, your career.
I started PipelineRoad a few years after that trip. I don’t think that’s a coincidence. The backpack didn’t teach me business skills. It taught me to distinguish between what I actually wanted and what I’d accumulated by default. And the career I’d been building — the path I was on before the trip — was mostly default.
The Moments That Stay
I keep a list on my phone of moments from that year. Not photographs — moments. Sensory memories that compress an entire experience into a single image.
The sound of temple bells at dawn in Bagan, carried across the plain by wind that smelled like dust and jasmine.
A woman in a market in Luang Prabang laughing so hard at my attempt to say “how much” in Lao that she gave me the fruit for free.
The Ganges at Varanasi at five in the morning. The cremation ghats burning. The devotion and the horror existing in the same visual frame, inseparable.
Getting caught in a monsoon in Kerala and sheltering under a corrugated metal roof with six strangers and a goat, all of us soaked, all of us laughing.
The blue streets of Chefchaouen at midday, when the light turns the blue walls almost white and the town feels like a photograph of itself.
A bus breaking down in rural Myanmar. The driver fixing the engine with what appeared to be a wooden spoon and a prayer. We were moving again in twenty minutes.
Standing at the top of a pass in Nepal, altitude sickness buzzing behind my eyes, looking at mountains that made every other mountain I’d ever seen look like a suggestion.
The Return
I flew home on a Tuesday. I remember this because I’d lost track of what day it was months ago and only rediscovered the concept of weekdays at the airport.
The re-entry was harder than the departure. Everyone tells you that. They’re right, but you don’t believe them until you’re standing in a grocery store with forty-seven options for cereal, unable to choose, because you’ve spent a year in places where the options were “yes food” or “no food” and that simplicity had become a kind of relief.
It took about three months to fully readjust. To stop mentally calculating the weight of everything I bought. To stop feeling guilty about owning more than I could carry. To accept that a settled life isn’t a failure of imagination — it’s a different kind of choice.
But something from that year never went away. A lightness. Not physical lightness, though I did pare down my possessions significantly. A mental lightness. The knowledge that I had functioned, thrived even, with almost nothing. That the floor of what I need is much lower than the floor I’d been living on. That safety net sits underneath everything else I’ve built since.
When PipelineRoad had a rough quarter, when a client churned and revenue dropped and the responsible thing to do was panic — I didn’t. Not because I’m brave, but because I’d lived on $25 a day in Southeast Asia and been perfectly happy. The worst case scenario wasn’t that bad. I’d been there. I had the receipt.
Forty liters. Eleven kilograms. Twelve months.
More than enough.