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 this decade of impermanence and travel indulgence isn't easy to shut off.

The Digital Nomad Dream

After backpacking around Europe and Central America with my friends in 2012-2013, I knew I had to choose a career path that allowed me the flexibility to travel. Growing up as a bit of a nerd, getting into software was the obvious choice.

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 while my friends were still in school, I moved my life across the world to become a surf bum.

A friend had introduced me to Shopify, and despite having zero professional experience, I started calling myself a "Shopify Expert Developer" on Upwork, a freelancing platform. I begged for contracts for weeks and got paid less than minimum wage for my first 5-6 gigs. It was 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 early 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.

The Nomad Bubble

We were all in the same headspace back then – reading Tim Ferriss, trading crypto, 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 small surf towns around the world, and did our best to justify our lifestyle choices as we were 'escaping the rat race'. We were all running from something... career expectations, relationship failures, taxes.

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 my stint in 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 most anywhere in the world with no limitations (I'm very lucky to have a Canadian passport).

I've now built a portfolio of small software businesses (bolle.digital) and have built my company in a way that gives me the flexibility to still do most of what I want: weeks off-grid camping, Fridays (and sometimes Mondays) off, no calls, no meetings, and the freedom to buy a flight to wherever I want without, for however long I want. It is truly the exact setup I dreamed off when I was 19/20 and envisioning my ideal lifestyle.

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 meant to be the grand finale - my favourite countries, seeing my old friends from past trips in Asia.

I tried settling in my hometown of Kitchener, Ontario 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 (boring, for me) 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 an apartment lease. My hands were 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 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, while I'm actively fighting the urge to book one-way flights on a weekly 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 and settle down.

But 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 for the past 10 years. 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, discussing life goals with a friend.

We casually chatted about our five-year plans, and I blanked when it came time for my answer. My subconscious took over and I blurted out: "I want to buy a sailboat and sail + surf around the world for a few years."

I thought I'd pushed away these feelings of travel, of long term adventure, for good, but clearly they still live inside me. I'm realizing this is the biggest question and dilemma in my life right now.

Do I truly try to push out those feelings of adventure and travel, force myself to settle down and stop moving — or do I give in to the temptation and book just another string of one way flights to escape Canadian winter?

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 the concept of leaving and moving?

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. I love stability, and having a good community of friends brings me so much joy. But after spending ten years building a life optimized for freedom, the idea of not using it to it's full potential feels like a 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 enjoy and friends I cherish, but 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.