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Reading it alongside another recent post, Europe Won’t Fix You by
stirred something deep in me. Both pieces explore a truth I’ve lived through and learned the long, hard way: that running away from the problems of your life — whether through movement or migration — doesn’t mean you’ve solved them. The dream of freedom can quickly morph into a quieter kind of trap, especially when it’s built on fantasy instead of foundation.And I get it. I understand the ache to be free. The thrill of buying that one-way ticket, of stepping outside the system. But the truth is: that’s the easy part. The hard part is what comes after — when the freedom you chased starts to feel like a cage made of air.
This is my story — not from the edges of the nomad movement, but from its messy middle. From someone who had to lose the dream to start building something better.
Not just a life in motion.
A life that can hold still — and still hold you.
Before “Nomad” Was a Noun
Before coworking visas and curated retreats. Before Instagram made it all look so glossy. Before “digital nomad” was even a buzzword, I was out there with one of the first travel laptops the world had ever seen — this chunky little thing made by a company that doesn’t even exist anymore, that weighed down my backpack more than I care to admit.
I left Canada with a one-way ticket and no clear plan. Just the feeling that I couldn’t breathe in the life that had been laid out for me. Everything back home felt too structured, too predictable. School, university, job, sitcoms after work, drinks on the weekend, retire, die. There was no room for wildness in that formula. No wonder. No me.
What I craved wasn’t just freedom — it was belonging. A place that felt like home, even if it didn’t look anything like the one I’d left behind.
In those early days, I’d pick up any online gig I could get my hands on. SEO articles for $30 a pop, written from hot, sticky internet cafés in places like the Hundred Islands in Laos. These weren’t quaint WiFi-enabled cafés with banana pancakes and kombucha on tap. These were bare-bones, sweat-dripping internet dens with machines that were maybe one step up from dial-up and a mouse that sometimes worked.
I remember one specific day so clearly — my fingers pounding out articles under flickering fluorescent lights while the power kept threatening to cut out, all so I could afford my next overnight bus and a few fried noodles. It sounds gritty and romantic in hindsight, but at the time it was just hard. Scrappy. Uncertain. And somehow, still thrilling.
I didn’t yet have a name for what I was doing. But I knew I was chasing something real.
Searching for Belonging in All the Wrong Places
After a year of bouncing around Southeast Asia, I was exhausted — in more ways than one. The weight of my backpack had become too heavy, and not just physically. I was tired of being in transit. Of always arriving, never landing. I had been looking for a place that felt like home, and ironically, I ended up in the one city I’d previously sworn I’d never live in: Bangkok.
I didn’t go there for the temples or the street food or the nightlife (though all three are solid reasons). I went because someone told me, If you want to make this women’s travel support business work, you need to be where the action is. And Bangkok is the hub of Southeast Asia. So I listened.
At the time, I was trying to get my startup, BlondeTraveller, off the ground — a support service for solo female travelers, back when solo female travel wasn’t even a category yet. I was still blonde then (hence the name), and still optimistic enough to believe that I could bootstrap a business from scratch in a city I didn’t even like, with zero funding and just a gut feeling.
Looking back, I admire that girl. She was bold. Maybe a little naive. But she was in it.
I thought I’d been clever by “escaping the 9-to-5.” But what I didn’t know yet is that digital freedom comes with its own set of chains. When you’re hustling to stay afloat in a foreign country, when your income fluctuates wildly month to month, when there’s no health insurance, no safety net, no one to call when you get sick or scammed or stranded — that’s not freedom. That’s just DIY capitalism with a passport.
But I kept pushing. I wanted belonging. I wanted purpose. And I wanted it to work.
Freedom, But Make It Capitalist
Eventually, I made the move to Koh Phangan — the place I’d always dreamed of living. You know the fantasy: a breezy little beach hut, a hammock swaying on the porch, azure waters stretching out in front of you, and me finally writing the book I’d been carrying around in my head for years.
Yeah. That didn’t happen.
Turns out, you can’t live on good vibes and mango smoothies. So I took on more freelance writing work. And then more. Until suddenly, I wasn’t freelancing — I was running an agency. I had clients like Shangri-La, Calvin Klein, The Ritz-Carlton. I was writing hotel content at midnight, managing writers across five time zones, juggling deadlines like fire. On paper, it looked like success. In practice? It felt like a slow-motion burnout.
There’s one memory that sums it up perfectly.
I had set up shop in an old wooden restaurant our landlord let us convert into an office. It was hot and humid and smelled like gecko poop, but it was mine. And while all my friends were off partying at my boyfriend's (now husband’s) waterpark — which was basically one big pre-party for the island’s infamous Full Moon Party beach rave — I was hunched over my laptop, trying to meet a deadline for yet another luxury brand’s newsletter.
That moment hit hard.
Here I was, “living the dream,” on a tropical island, surrounded by palm trees and boat parties and beach bars — and I was chained to a keyboard in a sweatbox in the jungle. My friends were drinking cocktails in the pool. I was triple-checking brand voice guidelines and dealing with unpaid invoices. I wasn’t free. I was just self-employed. And underpaid. And utterly exhausted.
Sometimes being your own boss just means there’s no one to complain to when it all gets too much.
The Dream Cracks Wide Open
If you’d looked at my life from the outside at that time, you might’ve thought I had it all figured out. I was living on a tropical island, had a growing business, a beautiful baby, and an enviable Instagram feed. But inside? Everything was unraveling.
My partner Fraser and I had split up. For nearly a year, we shared our baby on a week-on, week-off basis, trading the role of single parent back and forth like a relay baton. It was brutal and lonely, and the only thing holding me together was the fantasy that my agency was going to save us, despite losing client after client due to Covid marketing budget cuts.
And then came the casino.
A giant casino in Hong Kong had been in talks to hire my agency for a major, ongoing content contract. We’d been negotiating for months. The money would have kept us afloat for a year, maybe more. I’d pinned everything on it. My team was ready. I was ready.
And then one day, the message came: it wasn’t happening.
No warning. No reason. Just... gone.
I remember reading the email and staring at the screen for what felt like hours. And then, for the first time in a very long time, I let everything fall. I crumbled. Fully. I cried until my body hurt. I stopped answering emails. I didn’t get out of bed. I felt like I had failed — not just as a business owner, but as a mother, a partner, a person.
It was the final straw after too many years of holding it together.
People think paradise heals all wounds. But let me tell you something: if you’re falling apart inside, the palm trees don’t make it prettier. They just make it lonelier.
Redefining Freedom: The Roots We Carry With Us
These days, I don’t really identify as a digital nomad anymore.
But I also don’t exactly have a home.
Not a real, permanent one. Not the kind with familiar neighbours and a favourite café and a kitchen cabinet that always has what you need. Since stepping back from Koh Phangan and starting fresh in Spain, we’ve been in a strange, liminal space — trying to land somewhere, but still floating. There’s been terrible luck with housing, landlords, leases that fall apart at the last second. It’s been… exhausting.
And yet, even in the chaos, I’ve found something to hold onto. A quiet kind of structure. Not the rigid kind I left behind in Canada — the kind where your whole life is already laid out — but something softer. Something that moves with me.
Lauren Razavi wrote, “The most liberated nomads aren’t the ones who abandon structure. They’re the ones who build their own.” That line hit me like a brick.
I’ve had to build my own scaffolding. Not out of ambition or adventure this time, but out of necessity. I call it my mobile foundation — rituals and rhythms that ground me no matter where I am.
Each morning, I do yoga. I meditate. I oil pull. I rinse with salt and clove. I drink a strong tea made of ginger and turmeric. I take supplements to support my body’s needs. These aren’t fancy self-care moments. They’re survival. Anchors. Reminders that I can still create steadiness, even without roots in the ground.
Because no matter where I am, I can always find a yoga mat. I can always breathe. I can always find a way to care for my body and mind. I can always find tea. There’s always salt. These rituals help me show up for my family with something resembling presence, even when the logistics of life feel like quicksand.
This is what freedom looks like now. Not a plane ticket. Not a palm tree. Not a flexible schedule or an open road. But the ability to stay soft in a hard world. To build something that holds me — even when everything around me is shifting.
What Comes Next
Here’s what I’ve learned: freedom without support isn’t freedom. It’s just instability with a prettier filter.
We chased escape thinking it would set us free. But real freedom doesn’t come from quitting your job or booking a one-way ticket or hopping borders every 30 days. That’s just motion. Real freedom is the power to choose the kind of life that holds you. One with meaning. One with care. One where you’re not always rebuilding from scratch.
There’s nothing wrong with wanting to run. God knows I’ve done it enough times to understand the appeal. But eventually, the thing most of us are actually running toward isn’t adventure or novelty or palm trees.
It’s belonging.
It’s enoughness.
It’s feeling like we’re not just passing through, but building something — even if that something is still in progress.
So no, I’m not a digital nomad anymore. But I’m still out here, living abroad, carving out space where I can, building a new kind of structure. One that can travel with me. One that can stretch and bend and grow into whatever this next season of life asks of me.
To those of you also living in between — between homes, between careers, between chapters — you’re not alone. We’re figuring it out together.
And if you’ve ever looked around your so-called dream life and thought, This can’t be it, I promise you: it’s not. It gets better. It gets clearer. And one day, it gets real.
Not just a flight plan.
A foundation.
What do you think? Do you have some points to add, or perhaps refute? I’ve left the comments open to all, because I think this is an important topic. Particularly now, with so many people moving beyond their home borders.
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See ya in the comments!
Thank you. What a wonderful post. I enjoyed reading your story. Life is what you make it. It's good to be part of a community. To feel at home somewhere. I am an international house sitter. My husband and I like to take on mid to long term sits so we can stay in one place for a reasonable amount of time. We get involved in the community and like to live like a local, not a tourist. Travel is our passion and there is so much out there in the world to explore and wonderful people to meet along the way. All the best.
Kaila, what a beautifully written piece. You always do a great job of connecting external events to the deeper emotions beneath. I, too, am at war with the exhilaration of freedom and novelty versus the allure of comfort and stability, and I think I always will be. However, the peace I've tried to make with my life is the knowledge that I can have it all, just not all at once.