How We Quit Our Jobs to Travel: Our Journey from 2008 to Now

This was the most exciting and most difficult time of our lives, and there was a time when we thought we might break up over it.

A lot of Instagrammers, Bloggers and YouTubers (including us) are always talking about how great it is to live a freedom life.

One where you can work from anywhere in the world, hardly work any hours per week and have money rolling in thanks to passive income streams like digital product sales, sponsors, ads, and affiliates.

But one part they always seem to miss out on is the act of actually making that change.

Quitting a job isn’t easy. When we were leading up to this enormous shift in our lives, we had tons of questions running through our minds:

“What if this is the stupidest decision we ever made?”

“What if we can’t figure out a way to sustain this life on the road?”

“What if we can’t sell this house?”

“What do we do with all of our stuff?”

We were actually terrified leading up to the moment we quit our jobs.

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Having run this blog now for over a decade, with millions of people visiting it every year, we figured it was finally time to talk about the story of our life transformation.

How we went from $12,000 in debt working and 60-80 hours per week at jobs we didn’t enjoy, to traveling the world, working from the road, loving our jobs, and working a fraction of the hours that we did in Canada.

In this article, I’m going to share the timeline of our journey from our old lives, to this new one.

I’m also going to share some tips that I hope will help you if you’ve ever considered this type of transition, and I’ll share some resources that weren’t available to us 16 years ago, but are available now and can make the transition a lot easier.

A Backstory

For those of you who are new here, we didn’t always run remote businesses while traveling the world and living abroad full time.

So here’s a bit of backstory…

Up until 2008, we both had good jobs in Canada.

Not “good jobs” in that they were jobs that we actually enjoyed… but good jobs in that they paid well (I worked on the Oil Rigs and later as a heavy machine operator, and Dariece was a Real Estate Legal Assistant).

We were pretty young. At 24 we had everything set out in front of us.

We already owned a condominium right in downtown Calgary.

We had a nice car.

We were earning over six figures per year and we were growing our “nest egg” as they call it back home.

We had the new TV, the fancy clothes, and went on some pretty posh week-long holidays. We were living a good life for a young Canadian couple.

On the surface… everything was awesome. Which is why I think it came as such a shock to our family when we told them we’re quitting our jobs, selling everything and going to travel the world… but I’ll get to that later.

We weren’t trust fund babies and neither of us had education beyond high school, so we actually felt like we had accomplished a lot at a pretty young age.

But there was definitely something missing.

First of all… I hated my job.

I loved the pay checks for sure… but everything else about my job as a heavy machine operator was depressing.

I had recently quit my job at the oil rigs. That job allowed me to pay off the $12,000 worth of debt that I mentioned at the start of this article, but that job was even worse than the heavy machine operating job so I had to quit.

When I had all of that debt, I was convinced that that was a big part of the reason I wasn’t content with my life.

I would say things to myself like: “If I could just pay off all of this debt, then I’d have money to buy the things I want and I’ll be happy.”

But that didn’t happen. The debt was gone… money was in the bank… but that feeling still lingered.

That feeling of:

“This can’t be it… can it?”

I went from one gruelling, physical job to another.

It wasn’t so much the physical labor that I disliked. It was the culture of the workplace.

I was lucky enough to work mainly with one guy, Aaron, who became like my best friend at the plant… and there were some really nice people working there… but for the most part, nobody wanted to be there.

People complained on every short coffee break about how they didn’t get any respect from management, or about how so-and-so was such a lazy worker and they had to pick up all of the slack.

Older guys, the ones who had been there for 40+ years, were constantly cautioning me to get out while I was still young.

They’d say things like:

“When I was your age I thought I’d just work in this plant for a few years and pay off my debt and then find some work I really love… now I’ll be retiring here in a couple of years and didn’t enjoy a single minute working in this hell hole.”

I’m paraphrasing, but believe me, the actual conversations had a lot more expletives and negative sentiment than that. Plus they were repeated almost daily.

The atmosphere was toxic. It was mindless work that paid the bills, but did little else to satisfy any human needs.

The plant was devoid of sunlight, it smelled like chemicals, and it was deafeningly loud.

But the hardest part of the whole situation, aside from the atmosphere, was the fact that I was only allowed 10 days holiday per year.

5 days in the summer, and 5 days in the winter.

Barely enough to do any real travel, besides maybe an all-inclusive resort down in Mexico where we could lay on the beach, sip margaritas and try to recover from a year of constant work.

Dariece’s situation was quite a bit different.

For one, she got 15 days holiday per year (still not enough), but she actually enjoyed her workplace, her colleagues, and all the perks that came with working at a law firm.

She just didn’t like the pressure, stress and the whole routine of getting up early, dressing the part, coming home late, dinner…repeat.

She had a better office atmosphere, and she didn’t have to work graveyard shifts like I did.

But she was the more enthusiastic traveler of the two of us and it crushed her that she couldn’t have any significant time off.

We both felt like we’d already been working for 8 years of our lives that could’ve been spent doing something else.

The FOMO was real.

There had to be more to life than this, right?

But how?

The Lightbulb Moment…

It all happened on one of those short all-inclusive holiday trips to Mexico that pretty much all Canadians and Americans seem to take obligatorily.

For most of the trip, we did what everyone around us did.

We sat around the loungers on the beach and by the pool, swimming up for the occasional cocktail.

We dragged ourselves to a fancy 5-star a la carte meal each night and then passed out to repeat the next day.

The goal was to get as tan (or in my case, burnt) as possible so that when we went back to work people said things like:

“Wow! Someone’s been enjoying the beach!”

Those comments were like badges of honour for those of us who otherwise did little else besides work, eat and sleep.

I have to say… these trips were a lot of fun and they felt SO needed after the hard work we were doing back home.

But on this particular trip, one day we decided to do something different.

We hopped on an ATV tour to go check out some nearby cenotes and some local villages.

We thought we were being so intrepid by actually leaving the resort in Mexico, which is hilarious to think of now.

Looking back at the photos, I realize that this is one of the most touristy things we could’ve been doing in Mexico.

But still… the tour was a blast.

The moment that changed everything was when we passed by a local village.

The locals heard the ATVs approaching and they all ran out to wave hello.

Probably the same parents and kids did the same thing to every tour that went by.

But we had a moment with them.

Instantly I thought… I don’t want to just whizz past on an ATV.

I want to actually stop and walk around.

I’d like to ask them questions about their life… maybe learn some of their language… taste their food… find out about their lives and what they do for fun.

It was a total lightbulb moment.

A flash of realization in a young 23 year old kid who had only left Canada a couple of times to visit the US and, now, Mexico.

It was a sudden realization that there was an entire world out there to see and experience, and at this rate, I’d be working so much of my life that I’d hardly end up experiencing any of it.

That moment on the ATVs changed everything… or at least… the seed was planted.

A few days later, that short 1 week vacation came to an end and again the feelings of dread returned.

I knew I’d be back at work in less than 24 hours.

The plane would bring me right back to the chemical-filled plant where I’d go back to work for at least 6 more months before “earning” myself another 1 week holiday.

Part of me must’ve imagined at that point what it would be like to continue exploring the world full-time… but that thought was so far from my reality at the time that it likely didn’t linger long.

The two words that changed our lives forever…

It was probably around 3 months after returning home from Canada that it happened.

I had a particularly shitty day at work. My boss was screaming at me for a mistake that was the machine’s fault, it was 40°C inside the plant and I worked for 12 and a half hours straight with barely enough time to have water.

Days at the plant weren’t always like this, but this wasn’t the first really bad day at work and I knew it wouldn’t be the last.

I stormed out of the plant that day after my shift was over and swore to myself that I wasn’t going to work there forever.

I was going to take the advice of the old-timers and not waste my entire life making plastic bags for big corporations.

There had to be more to life than working for a pay check that I’d use to buy stuff I didn’t need, to impress people I didn’t like, all while living a life that I didn’t even sign up for.

I got in my car and sped out of that parking lot like I was on a mission, but at that point I had no idea what that mission was.

When I got home, I went onto the internet and started Googling (Or maybe it was MSN back then? I don’t remember…), but I was searching for: “what is ‘backpacking’?”.

I remembered when I was a kid my aunt did this “backpacking” thing around Europe, but I didn’t even know what it really meant.

How do you get from place to place?

Where do you stay?

How much does it cost?

How do you communicate?

Somewhere in those frantic web searches I happened across a blog about gap years.

I don’t know, maybe it was Nomadic Matt’s blog. He was probably about the only one travel blogging back in 2007.

But I was suddenly introduced to the idea of an entire year off work.

As a Canadian, this concept had never even crossed my mind.

We don’t really do “gap years”.

We finish high school and then either go to work or college. There’s no “time to find yourself“.

There’s barely time to find a yourself a job.

This new keyword took me down a rabbit hole of intrepid travellers who saved up money to literally travel the world for a year or more.

By the time Dariece came home from work, I was absolutely buzzing.

She barely made it through the door when I asked her that fateful question….

“If you could travel anywhere in the world for a year… where would it be?”

Without any hesitation she answered “Southeast Asia”.

Those two words changed our lives forever.

So that was it. We would make this happen… no matter what.

It’s time to quit our jobs…

The idea of quitting our jobs was terrifying.

We were well aware of how fortunate we were to have them.

We knew that if we stayed at those jobs, our lives would be pretty much set.

We’d always have the bills paid.

We’d be able to easily save for our future.

We’d be able to afford a comfortable house and a nice car…

But we also knew that life wasn’t for us.

We wanted to see the world. We wanted to live the next 50, 60, or 70 years of our lives without the regret of never giving it a shot.

We wanted to live every moment like it was our last (as cliche as that sounds, there’s no better way to word it).

And while we had no idea how we’d make that happen beyond the one year we’d saved enough money for… we knew there had to be a chance.

If some random blogger online can do it… surely we can too.

So within about 10 months since the 2 fateful words were spoken, and thanks to working A LOT of overtime and managing to sell our house and our car, we had about $25,000 CAD to travel with.

Our goal was to travel the world on $50 CAD per day including all flights, accommodation, food and experiences.

That would be a total of $18,250 for the year, and then we could come back with a little bit of buffer money to figure out our next steps.

Even with more money in our banks than we had ever seen before… we were still scared to quit.

Our families were supportive of the entire idea of us traveling, but we could hear the worry their voices when we told them we were quitting our jobs.

There were a few “Are you sure you want to do this?”.

But we knew we had to do it.

However… actually quitting my job wasn’t so easy.

I’d love to tell you that I still remember the day I quit like it was yesterday.

That I walked into my bosses office and threw my letter of resignation at him and said “I QUIT!”

But the truth is, I barely remember it.

I remember telling him I was going to go traveling, and I vaguely remember him saying something about me being able to come back when we returned… but the rest is a blur.

Honestly I think part of me blocked out the memory.

Even though looking back now, that was easily the best decision I ever made, and I can’t even imagine my life if I had stayed there… I think it was so terrifying at the time that I just lost the memory of it.

Dariece and I almost break up…

Not surprisingly… selling a house and a car, storing all of your things, working 80 hours per week to save money and then uprooting your life to travel to a foreign land is pretty stressful.

Stressful enough that it almost broke me and Dariece.

Not to mention, we had only been dating for about a year when we began planning this first world trip, so we didn’t even know if we were going to get along while traveling.

As the trip deadline approached, we were arguing about everything and it was stressful.

Now, after 17 years together and having pretty much no fights that entire time… it’s clear to us that the pressure was just getting to us back then.

We’ve come to realize that during the biggest transformative times in our lives, our old selves hold on to how things were.

We want to keep the norm. We desperately grasp on to what we’ve known for a long time and that causes friction within us that translates to frustration between each other.

But what we’ve also learned is that in those moments come the biggest positive changes in our lives.

Luckily we made it through the bickering and we boarded our flight on November 17, 2008.

And yes… it was an enormous positive change in our lives.

Lift-off

While the memory of me actually quitting my job still evades me… the memory of the plane wheels leaving the tarmac in Calgary International Airport on November 17, 2008 are engraved in my mind forever.

That feeling was one I can’t really explain.

All of the stress and anxiety of selling the house, saving enough money, storing our things, quitting our jobs, telling our families, and then planning an epic 1 year trip around the world suddenly left and I could physically feel a weight lifting from my shoulders.

On top of that, it suddenly hit me that I’d just left Canada and I wouldn’t be back for a year.

I had spent the last 8 years of my life without more than a week off per year, and before that I was in school since I was 4 years old.

This would be the first time in my life I’d have complete freedom for more than a few weeks at a time.

Experiences like that incredible ATV tour in Mexico could happen to me every day for the next 365 days.

I had no idea what to expect… but I knew it was going to change me forever.

Two and a half years on the road… how do we do this forever?

Fast forward to 2012. We finished that first year long trip around Southeast Asia, which actually ended up being 13 months.

Then we went back to work our same jobs in Canada to save up for another trip. That’s right, when both of our bosses found out we were back in the country, they called to offer us our jobs back!

But this time it wasn’t just Southeast Asia, it was a world trip.

And this time we swore to ourselves that we’d find a way to keep traveling and living abroad forever.

But then there we were…. again nearing the end of that trip.

We’d had the most amazing 2.5 years on the road that we could’ve ever imagined.

We made so many friends, learned so much, tasted so many different types of food… it felt like our minds were expanding with every day on the road.

But then the same familiar dread returned.

The bank account was low and it was going to be time to go home and get those same jobs back… again.

If they’d even take us back again.

“Not this time”, we thought.

We’ve gotta figure out a way to make this our lifestyle.

It all came to a head when Dariece had an emotional breakdown on a beach on Koh Phangan Island in Thailand.

We had a few weeks, maybe a month worth of travel money left and it was inevitable that it was going to run out.

Dariece started crying on the beach when it hit her.

There was nothing that we both wanted more than to keep traveling around the world.

How could we possibly go back now?

We had become so detached from our 9-5 jobs and that lifestyle that it didn’t even feel like it would be possible for us to go back.

We were like puzzle pieces that no longer fit into the picture of our home lives.

Seeing Dariece crying on the beach set something off in me.

She was terrified of what all of this meant, so I told her what any young guy probably says when his girlfriend is crying and he has no idea what to do….

“We’re going to figure this out. Don’t worry. We will make this work.”

From there I went straight online and started looking for ways to make money on the road.

We were supposed to have found jobs on this trip, but we got lost in the excitement of travel and never even looked… so now it was do or die.

I found a few listings of schools in China who would hire English Teachers but all the forums I was reading said that you needed a University Degree to get a job, something both Dariece and I didn’t have.

I went back to Dariece and said: “We’re going to China. Once we get there we’ll find a job.”

We had no idea how we were going to do that, or if it would even be possible to work without a degree, but we went anyway.

A couple of weeks later we were on a plane to China.

Teaching in China… the gateway to remote freedom.

We were in China for a week or so when I finally decided to take the job hunt seriously.

We had seen a listing for an English teaching job posted at a cafe on one of the first few days in the country, so one Friday afternoon we decided to go around to a bunch of different cafes and look for similar listings.

Sure enough, on bulletin boards in pretty much every cafe and small restaurant, there were listings for English teaching jobs with emails printed on them.

I probably emailed about 5 or 6 different schools that day.

Then we waited for replies. But of course it was the weekend.

So Saturday passed…

And Sunday…

And then just as the idea of teaching was being replaced by more epic travels around China… we got an email.

Then another…

Then another…

I’m pretty sure every single school emailed us back.

Within 10 days we had hopped on a couple of calls with the head of schools and settled on Shane English School in Yangzhou, China.

We lucked out.

With so many horror stories coming out of China about schools not paying teachers or not helping them find accommodation, but we had the best experience ever.

We loved teaching our students and our one year contract flew by.

China was a blast.

Remote freedom at last…

Just before we got the job teaching English in China, we had started a blog.

It was more just a way to share our travels with our friends and family, but we did know of one blogger who was actually making money from it.

His name is Johnny Ward and today he’s a good friend of ours, but back then he was just a god-like hero who had somehow managed to fund his travels by sharing photos and writing blog posts online.

Because of Johnny’s inspiring blog posts about making from his blog and social media, we kept at it.

We worked on our blog the entire time we were teaching English in China.

We didn’t work a lot of hours on it. We had to teach around 20 hours per week, so we’d spend about 10 or 15 hours per week on the blog.

Even though at one point I gave up on it because I didn’t feel like it was going anywhere… luckily Dariece kept up with it, and after just 8 months we earned a little bit of money from it.

We sold calendars and gift cards with our photos on them which mostly our family bought from us.

We made $588 in the month of December 2012 and we were ecstatic.

Then we made exactly $0 from the blog for nearly 6 months until in June of 2013 the business made it’s first “real money”.

We started getting advertisers contacting us, and despite not knowing ANYTHING about how to start a successful blog, slowly the blog grew and so did the income.

We went from $500 to $5,000 per month, $5,000 to $25,000 and the revenue just kept growing from there.

Suddenly we had a real business.

We were traveling the world and living the life we always dreamed of, doing something we loved and earning multiple times more than we ever did in Canada.

We could’ve never imagined this…

Honestly when we look back at those first few blog posts we wrote, or those first few shares we did on social media, we could’ve never imagined that it would turn into what it is today.

It still amazes us that our businesses run on autopilot. Generating enough income to travel the world, live overseas and save for our future.

We are so grateful every day for this life that it has created for us.

And the fact that we’ve been able to do it not just once, but 4 times over, and the fact that the students in our blogging courses have followed our methods and had the same results, means it’s repeatable.

It’s an amazing time we live in right now. We thank the “internet gods” every day for allowing us to have a creative outlet, build a fun community, and earn a full-time income all while traveling around the world and working from our PJs.

I know this sounds too good to be true… and 12 years ago if you told me I’d be doing this today, I’d say the same thing.

But there are thousands of people turning their passions into real, life-changing businesses online and it’s happening every day.

Why isn’t everyone doing it?

Over the years, our courses including our Beginner Blogging Course and our Complete SEO Course have helped over 1,000 people start their own online businesses.

But we know from teaching all of those people that the biggest thing when it comes to being successful building a remote business is having community, accountability, and guidance to keep you focused on the right things.

In my opinion, there are a few reasons why so many people fail…

Feeling overwhelmed…

There are a million things people think they have to do when they first start building a brand online.

But really, you just need to focus on a few things, and do them right.

Picking the wrong niche…

For one, you need to pick the right niche right off the bat. People spend years aimlessly posting about THE WRONG THING simply because they didn’t narrow down their audience, didn’t do the right market research, and didn’t ask themselves the right questions before getting started.

This game can be lonely…

Everyone needs accountability. They need to know that what they’re doing is going to work and to have some encouragement along the way.

Accountability from a mentor, and from a group of people in a similar situation is vital in actually being successful at this.

I honestly believe that the vast majority of people give up just before they hit it big, and it’s not because they aren’t good enough. It’s because they didn’t have someone there to tell them that they were on the right path.

Introducing The Creator Kickstarter Coaching Program

This is why in our coaching program we have our exclusive Niche-Finder Framework. This is the framework we have used to find out which of our passions is actually a viable business plan.

We also have live, one-on-one AND group coaching to keep everyone accountable and to make sure all of the people in the program are on the right track.

And we also have lots of fun, but super useful pre-recorded lessons and modules to walk each person through EXACTLY what is needed to build a remote business quickly.

If you’ve always wanted to turn your passions into a remote business that can allow you to spend more time with loved ones, travel the world, and live a truly free life… then fill out our quiz!