Hi, I'm Kaila: Reintroducing Myself and My Life Abroad Journey

How failures, love, and a tropical island shaped the journey behind Home Abroad.

Jul 06, 2025

Hi friend — thanks for stopping by.

This story comes from deep in the archives, and it feels like a time capsule of everything I’ve learned (and unlearned) about living abroad. So much has shifted since I first hit publish that re-sharing it now feels like a way to honour where I started — and where we’re headed next.

Home Abroad — and the community we’re building here — is about more than just living abroad. It’s about the messy, beautiful, imperfect journey of trying, failing, learning, and finding a way to belong far from where you started.

If this resonates with you, I’d love to have you join us.

Or become a paid subscriber to unlock premium posts, behind-the-scenes updates, and tools to help you build a life abroad with more ease and meaning.

I feel like I need to start at the beginning, because this blog started with a lot of my friends and family who already know me, but there's been a lot of new people joining, so I think it's about time for me to reintroduce myself.

Hi, I'm Kaila, and I've been living abroad for my entire adult life which I'm pretty sure qualifies me to talk about what it's like living in a place that's a completely different culture, language, race, climate, continent, everything to the one you grew up in.

My living abroad story starts with me moving to Japan with my long-term boyfriend and being dumped three weeks after hitting Japanese soil. I don't know how it ends, but I'm currently 18 years deep, married to a Scotsman with a 4-year-old cross-cultural, strangely accented boy, running a property development company on one of the most desirable tropical islands in the world.

Fraser and I met in the toilets of a beach bar during Thai new year on his 21st birthday. I was 26. He told me he'd come visit me at my home in Bangkok. I was sceptical. But he did.

I was even more sceptical when he said that he was going to come back a month later. But he did.

And he never left.

Fast-Forward to Family Life

We were married 7 years later not far from the toilets where we met on that fateful night in Koh Phi Phi, at a beautiful resort in Krabi, Thailand, in front of over 100 of our nearest and dearest who'd flown in from all over the world.

A month later, I was pregnant. We went to Scotland to have Hudson Ron, whose middle name comes from my dad's.

Ron had passed away from melanoma a few years before. Having had a taste of wealth before losing it all, my dad had spent his entire life trying to scrape it back. He never did. But he left us enough of his life insurance to buy land with, I guess in hopes that we would finish the job.

"Your money is always safest in property," he advised me one afternoon over a ron y Coca at his favourite restaurant on Lake Chapala, just a few blocks from his and my mom's house in Mexico, where they'd moved around the same time I moved to Bangkok.

We later held his wake there, too.

It was great advice, and much needed since our other projects had been total flops. There was a waterpark called Slip ‘N Fly (where flops were so common that a signed safety waiver was necessary for each participant). And then there was The Content Castle, a one-of-a-kind writing home where writers could pay their rent in words.

Both achieved some degree of success — the waterpark more so than the writing house. Both floundered and failed right before COVID hit — which would have been their final blow anyway, had they not.

But it doesn't end there. I've tried and failed at all kinds of businesses since moving abroad.

My Far-Flung Flops

First there was BlondeTraveler — which I suppose was an early and far too complex version of this very blog. It was a support service for women traveling Southeast Asia. But it was also a blog, and a discount card, and at one point I was even in talks about starting our own travel insurance. It was trying to do too many things, and hence, it never made a dime.

Then there was Archipelago Communications, my marketing agency. When I landed a social media contract with the Shangri-La hotel group, I decided to double down and open a social media agency. It was in the golden years of social where no one really knew what they wanted, why or how. So clients were throwing money at people who did, expecting mega ROI. And when it didn't produce, they wouldn't understand.

It was incredibly stressful.

So I pivoted and shifted into the content marketing space. Blogs, I reckoned, were much more straightforward than social media. I had good writers on my team who could research and write excellent blogs. Plus, having started my career in journalism, blogs felt more aligned with my path.

Me at The Content Castle when it first opened.

That's when I opened The Content Castle, which produced the writing for the clients I'd signed at Archipelago. It was a cool idea, but the deck was stacked against us from the get-go.

First of all, we were massively overpaying in rent. Which put our overheads beyond our reach. Which meant that residents had to write more words per week than they were comfortable with so that we could stay afloat. Plus, me being on another island (I live on Koh Phangan, The Content Castle was on Samui meant that I couldn't be there all the time — a recipe for disaster.

I tried my best to keep everyone motivated and provide more and more benefits for everyone staying at the house. But no matter what I did, our in-house managers kept rebelling and saying that they were overworked and underpaid. The residents too kept saying they couldn't keep up with the content demands.

I dug deep and tried everything I could to get us high-paying content clients so I could lower the weekly word count for the residents and pay the manager more. I slashed the weekly required word count in half. I even funded a second assistant manager out of my own pocket to help, but it still wasn't enough.

My dream house for writers — a concept I'd put so much time, effort, and money into, slowly devolved into a nightmare. My manager quitting when I was across the world in Scotland and 8 months pregnant was the final nail in the coffin for The Content Castle. She took her sidekick I'd hired to help along with her and managed to turn all the residents against me as well.

Belly full of a soon-to-be-born baby, I sunk to the floor in my in-laws’ guestroom and decided it was time to pull up the drawbridge.

It was around the same time that we decided to sell Slip ‘N Fly. Which would have been great timing if we'd ever received the money from that sale.

Because that was also when Hudson Ron came into the world.

I began applying for writing jobs at my in-laws' place in Edinburgh with a newborn attached to my breast, navigating the laptop and typing with one hand. We simply couldn't move back to Koh Phangan if I didn't find one — Fraser had carpentry work in the UK, but back then before we were building villas, the carpentry jobs on the island were few and far between.

Just in the nick of time, I landed something. It was a writing role for an AI startup building intelligent chatbots based in Germany. It paid well enough for me to support our needs and it was only part time, so I could keep trying to make Archipelago Communications work. (I'm tenacious AF, you'll see.)

I pivotted again, closing The Castle to breathe life into the Digital Nomad Writing Club. It was basically an online version of the writing house.

I hired a small core team, and we worked our butts off. Our goal was to offer even more benefits to being part of the writing club than our residents had been receiving at The Castle.

We built an online writing school.

We held weekly Zoom workshops.

We paid for special writing software for our members.

We even offered one-on-one tutoring.

But without the accountability of being in a house where you have to face your manager and fellow team members each day, it turned out to be almost impossible to stay on top of our client content demands. Not to mention the fact that the quality of the writing our students were producing was incredibly unreliable. We ended up doing a lot of the client writing work ourselves, which entirely defeated the point of having the school, and actually just doubled our workload.

(Stick around and you'll see that I do tend to create a lot of unnecessary work for myself.)

There were a lot of last-ditch attempts to keep the writing school and content agency afloat during its final year.

Laying Our First Foundation

It was also around the same time we started building a villa on the land we'd bought with the money my dad left us. We'd bought the land years before upon our sorrowful return to Thailand after my dad's passing.

But we had no funds to build on it. So when a friend gave us the idea to get architectural drawings created and sell a villa off plan, we jumped on it. And no sooner were the drawings made then we met someone who wanted to buy it.

Contract signed and funds in our account, we secured a contractor and started building our first two villas — one for the buyer, and one for us to sell to someone else.

But on top of the demands of having a newborn baby in a foreign country with very little support from friends or family, we couldn't hack it. COVID was ravaging the world and decimating our island, making our already disconnected lives even less bearable.

Unable to cope, Fraser and I separated. I found a beach bungalow at a great deal (thanks COVID) and moved in there. We shared Hudson one week on one week off.

It was heartbreaking. I never felt so alone in my life.

And when I finally, painstakingly let the pillars of my house of cards marketing agency crumble, I actually felt more relieved than anything.

I knew it was finally time to surrender to defeat. Life had beat me. I thought I'd hacked the system by moving abroad, but the realization was slowly starting to sink in that you simply can't enjoy paradise if you don't have your basic needs met.

I was a nervous wreck whose anxiety was eating her alive.

The combined weight of the last few years…

From the torment of having to travel back and forth from Mexico to Thailand and back again while I watched my dad wither and die.

To the stress of running a barely legal business made up of people who hated me on another island.

To the duress of selling our waterpark shares and being lied to for years about the whereabouts of our payment. (When we could have really, really used the money.)

To the rollercoaster that was trying to pivot and pivot and pivot until I was basically doing pirouettes to keep my overly complex companies alive.

To the soul ache of having split up with my partner and best friend and the duress of then trying to be a single mom coping with burnout during a time of total isolation on an already isolated island.

To the sheer heartache of feeling I was neglecting my baby when all I wanted was to be close to him.

And it actually felt good to finally admit that I didn't have life by the balls like I was trying to portray.

A Turning Point

And in its first kind gesture in a long time, the universe responded with a smile.

The guy who had bought our first villa was now interested in the second one. It was still 2 months from completion.

When the funds from the second sale hit our account, we were finally able to breathe for the first time in years.

I needed to decompress. Take a break from entrepreneurship. Spend time cuddling my baby.

Fraser started making moves to turn our villa ventures into a company.

He built up a relationship with the most sought-after architect on the island. Bruno began feeding him construction jobs when he started to see how capable Fraser was.

Eventually, Sand & Stone Development was born.

Meanwhile, I landed a part-time writing job for a heavyweight copywriter that paid well and didn't require too much of my time. Which meant I could work and spend lots of time with Hudson.

But eventually, inevitably, my love of writing for myself took hold.

Sure, I was getting paid to write. But it was all editing other people's words. Or writing stories about products or services I had no stake in.

I missed having a blog — something I'd always kept, from Japan to Bangkok, Bangkok to Koh Phangan.

Which is when my client introduced me to Substack. He asked me to research it in view of him potentially hosting a blog on the platform.

He never ended up going for it, but I went ahead and started my own channel.

Which you're reading now.

I also decided it was finally time to start my book. Tell the story I've been living since I left Canada. Originally, it was a guidebook. A guidebook to living abroad. Or, Girls’ Guide to Living Abroad, if you will.

Then I formed a writers’ group together with some fellow islanders who were also writing their books. Their feedback spun me in a new direction. Through my blog posts, which were a combination of guidebook-type posts and personal stories, it became clear that my more personal stories revealed the same lessons as the guidebook-style posts, while being infinitely more interesting.

So I pivoted. Again. I began turning my story of living out all of my adult milestones in a foreign country, culture, and climate — the very story you're reading right now, in fact — into a book.

My story of heartbreak and soul-tormenting anxiety and of bad decisions and treacherous failures on an island people seek out to forget those very things.

In addition to that, I have plans to transform this blog into an online home and community for those living abroad. Its new name: Home/Abroad (still working on the logo…). Its mission: to provide people living abroad with a cozy online space for culture, conversation and connections.

I’m working on an editorial calendar for the year and am also recruiting more writers to be part of my team. (If you’d like to write for this blog, apply here.)

Letting Go & Moving On

Now Sand & Stone Development is building 14 villas, including our own. Hudson is nearly five. And we are on the cusp of finally, after 13 hard-AF years, being able to enjoy the perks of living abroad.

I read something recently that gave me hope for the future. It was in Kabil Gibran’s book The Prophet. I realized that I had not just one but two copies of it on my bookshelf, so the universe was probably trying to nudge me to read it.

“The deeper that sorrow carves into your being, the more joy you can contain.”

On the back of a friend of mine recently pointing out that drama has seemed to follow me since he first met me, it gave me pause. Maybe all the hard lessons I have learned have borne deep into my being only to soon be filled with the joy and freedom living abroad can offer.

Maybe now, it's my turn to finally have some fun.

Stick around. If they're anything like my life’s last few chapters, the coming years are going to be one hell of a ride.

If you’ve made it all the way here — thank you. Sharing these chapters of my life abroad is not only vulnerable but also liberating, and I’m so grateful you’re here to witness it.

Have you faced your own big pivots, heartbreaks, or adventures abroad? Share your story in the comments — I read every single one.