The Digital Nomad Hangover

Despite recently signing a one-year lease for my apartment in Vancouver, everything I own still fits in a couple suitcases. I've got a one-way flight to Bangkok booked in October, three half-planned international trips on the horizon, and a villa in Uluwatu reserved with some friends that I may or may not show up at.

I spent ten years perfecting the art of leaving – eight to ten months annually bouncing around the world, freelancing and building software from wherever had Wi-Fi and waves. Now I'm 30, have been "settled" in Vancouver for almost a year, and am quickly discovering that a decade of impermanence doesn't just switch off when you decide it's time to grow up.

The Digital Nomad Dream

In 2015, I finished the shortest programming diploma I could find in Ontario and immediately flew to Bali with a couple hundred bucks in my pocket. I'd heard there was decent enough Wi-Fi and amazing surf – so I left my friends, family, and any pathway to a traditional life behind.

A friend had introduced me to Shopify, and despite having zero professional experience, I started calling myself a "Shopify Expert Developer" on Upwork. I begged for contracts for weeks and got paid less than minimum wage for my first 5-6 gigs. It was objectively horrible work, but it covered surfboard ding repairs and daily nasi goreng from the local warung. I was happy.

Those first months were like living in a dream. Surfing all morning, coding all day, Sandbar and Old Mans in Canggu every Friday night. Dozens of us digital nomads crammed into Dojo Bali, hacking away at side projects until 2 AM, launching on Product Hunt, hoping to make enough for next month's visa run.

We were all in the same headspace back then – reading Tim Ferriss, trading crypto before it was cool, trying to optimize our lives for maximum freedom and minimum responsibility. We swapped tips on visa runs, compared notes on the best co-working spaces, and tried to justify our lifestyle choices with talks about "designing your ideal life" and "escaping the 9-to-5." We were all running from something... career expectations, relationship failures, suburban futures, maybe taxes - but we dressed it up as running toward adventure.

By no means was I close to being the first digital nomad (I know people who've been on the road since 2009), but I do think this era of 2014-2017 was one of the first large waves of this lifestyle making the rounds.

After Bali, I spent almost a decade chasing that same feeling across 60+ countries. Spending months living in countries that I didn't even know existed when I was a kid. The pattern stayed the same: find a co-working space in a new city/country, connect with other travellers, share stories of your adventures, become friends or more with locals and other travellers, and then fly off to the next spot when your visa expired. Rinse and repeat.

It was an unmatched level of freedom. I made very little money for most of this period, but with only a backpack of possessions and a very low bar for where I'd sleep, I could fly anywhere in the world with no limitations. The whole lifestyle was about optimization – minimize possessions, maximize flexibility, avoid anything that looked like a commitment.

I still check flight prices every morning like other people check the weather. Old habits.

The Year I Said I Was Done

After a decade of frantic movement - hundreds of flights and Airbnbs, thousands of meals in hole-in-the-wall restaurants, a couple of ruined/lost passports - I decided it was time to settle down. My last big trip (cycling around Taiwan, a few months in Japan, bouncing around Singapore and Malaysia) was supposed to be the finale.

I tried settling in my hometown of Kitchener first. My childhood friends and parents nearby, most of them getting married and having kids. "It's about time," I told myself. I was 29.

After a few months of normal life in southern Ontario, I got antsy. I booked a three-week camping trip in British Columbia and fell in love with Vancouver. In October 2024, I made what felt like the biggest decision of my life: signing a one-year lease. My hands were literally shaking as I signed the paperwork.

One year in one place? I hadn't done that since I was 20.

I told everyone this was it – where I'd settle down, find a partner, do the thing. Buy furniture. Build something lasting.

Vancouver Is Amazing

I've been here almost a year now, and Vancouver is objectively amazing. Every morning I run the seawall, one of the most beautiful ocean-front routes in the world. Every weekend I'm hiking, camping, or at drinking beers at Kits Beach with a great community of friends. For someone who lives for the outdoors, this city is paradise.

But there's no surf. It rains for months. It's outrageously expensive. Most people don't stay here for long due to the insane real estate prices.

A part of me still thinks there is a better place out there, one that checks all the boxes. That part of me keeps things in suitcases ready for a last minute trip, browsing surf reports across the planet.

My friends back home are buying houses and having kids meanwhile I'm actively fighting the urge to book one-way flights on a daily basis.

The truth is, I've set an expectation in my mind that I'd 'do the thing' – stay in one place, build a community, find a girlfriend.

I can't shake the feeling that settling down now would be selling short the freedom, money, and health I've worked hard to build. These next five years feel like prime time to actually use what I've optimized my entire life for.

So why would I stop?

"Where Do You See Yourself in Five Years?"

This all came to a head recently with a girl I was seeing. An amazing connection, we worked really well together. We were talking about our futures, and on paper we aligned – marriage, kids, a house in the future (probably back in Ontario given Vancouver's insane real estate).

But when she asked about my five-year plan, I blanked. My subconscious took over and I blurted out: "I want to buy a sailboat and sail around the world for a few years."

She was shocked. So was I.

I thought I'd pushed away these feelings for good, but clearly they still live inside me. We've since stopped seeing each other. It's been rough, dealing with this internal conflict – the opportunity to truly settle down versus the ever-lingering pull to book a flight for a multi-month adventure.

It's not commitment issues exactly – it's that I've trained myself to see every commitment as temporary, every plan as reversible. How do you build something lasting when your entire identity is built on leaving?

The Question Without an Answer

There are no clean solutions. I could compromise – take shorter trips, date someone who travels, move somewhere with waves. But that's not really the problem. The problem is that ten years of training yourself to leave creates a mental architecture that doesn't just disappear.

Maybe not a year-long motorcycle trip through Africa anymore, but a few months in Asia sounds reasonable, right? The issue is I do want family, kids, a home. But after spending ten years building a life optimized for freedom, using none of it feels like the ultimate waste.

I used to think this was a phase, something I'd grow out of. Now I'm starting to realize this might just be who I am – someone who needs both flexibility and routine. Freedom and grounding.

So here I am about to turn 31, in one of the best cities on the planet, with work I love and friends I cherish, still unable to buy furniture because it feels too permanent. Still fitting my entire life into suitcases despite having an address that says I'm staying.

I still haven't booked a return ticket from that flight to Bangkok in October.

Is this freedom or is this broken?