In 2011 I went to a dinner at a friend’s - one of my old high school teachers - and at some point in the conversation he asked “How’s your job?” I had a great job, but I really wasn’t happy being in Halifax anymore. I remember answering that “my job’s awesome, there’s no other job I can imagine that could be better…but god, I really just want to work on my own stuff. And I wish I could travel.”
It was a feeling that had been building up for a long time.
The next morning my boss fired me and I remember a feeling of so much freedom and releif that I didn’t even ask why. I just kind of lit up inside and said “ok”. He eventually did tell me why, it was because I was so focused on my own stuff and not the company’s stuff, but while he was explaining that my mind was already racing with thoughts of “I can do anything now.” Before this I’d been struggling because I knew I wanted something else, but at this point in my life my do what you’re passionate about muscle was still in development and I needed this push.
Now I had to choose what to do next. I’d built a video aggregator which was getting a few hundred thousand views per month - a few friends wanted to invest and some others in the local community were starting to pay attention to me for the first time, mostly due to the reputation of the company I had been working in. The thing is, the only person who didn’t seem to think it was a real business was me. I had built it to learn how to code something other than a basic WordPress theme, and I’d achieved that goal while building something cool that I used myself, but I didn’t really want to dedicate years of my life to this thing.
About a week later I did what my gut told me to - forget the video aggregator. I was going to sell everything I owned in Canada, put my life into a duffle bag, book a one-way ticket to Thailand and figure the rest out when I got there.
My old boss referred a freelance client to me and taught me a bit about his time freelancing. I decided that I’d wait a few weeks to see if the freelance work kept coming in steady, and when it did, I booked my one-way ticket.
Thailand
Everyone was telling me to get a job - nobody really thought the whole one-way to Asia ticket was a good idea, but I didn’t really care. I’d just say “no, I’m going to Thailand” and ignore them.
A blog post had called Thailand the best place to start longterm travel, which is why I was headed there - other than that blog post I didn’t know much about it. I booked a hostel in Bangkok and a hotel in Chiang Mai, to try both hostels and hotels since I didn’t know if I’d like staying in a hostel. Bangkok was the place that I’d heard of so I flew there first for two weeks, and I’d read online that Thailand’s seedier tourists tend to steer clear of Chiang Mai so I decided to head there too for a week, taking a train between the two.
I spent most of my time in Bangkok getting on the metro or into a water taxi, taking it as far away as I could, then getting out and trying to find my way back to my hostel on foot.
It was a lot of fun. I remember taking the water taxi to a random place and deciding “I’ll get out here” - I was getting weird looks from all the Thai people on the water taxi so I knew this was a strange place to get out. It was military barracks for miles - eventually I made it to something like a sparse city area, where I stumbled onto the last metro stop on the outskirts of Bangkok. I made some friends at the hostel, and I spent a lot of time doing freelance work, but my Bangkok experience was mainly about this type of walking around in random directions.
After taking the train to Chiang Mai, I settled into the hotel and started to do the same type of on-foot exploring, but this time with a direction in mind: going hiking, to the old city, or visiting the aquarium and zoo. I’d work in cafes, then walk for hours in a new direction.
Around the same time I was fired from my job I had quit a correspondence MBA program I’d been taking for about a year. The day that I quit I bought an e-Reader to undertake self-education as an alternative, and I spent a good part of my time in Chiang Mai reading and learning. This is a picture of a mountain where I’d hiked to spend the day reading.
Singapore
I’d planned both the Thailand and Singapore legs before leaving Canada - there was a tech conference going on in Singapore so I thought it’d be a good way to make some friends. I’m still friends with the people I met there, I see some of them all the time, so the conference was time well spent.
I started hanging out with a guy named Haegwan Kim which was lucky for me because besides Haegwan being cool, he also had a lot of cool friends. One of his friends was a well-off Japanese banker who started showing us around Singapore. I guess due to Japanese culture he treated us anywhere we went (because he was older than us). We then started hanging out with another of Haegwan’s friends Loki, who at the time of writing I’ve now seen in I think 4 countries since meeting in Singapore.
After a few days the conference was over, Haegwan was headed to the airport so I decided to share a cab and go with him. When I got to the airport I went to find an airport computer - I didn’t have a plane ticket to actually go anywhere yet, so I needed to figure out where I wanted to go.
Malaysia was close and I had an aunt there, so I booked a ticket leaving a few hours later.
Malaysia
Malaysia was interesting.
My aunt had moved to Malaysia about 10 years earlier and had been living in Kuala Lumpur ever since. I got her number from my parents, called her a day or two after arriving, then went out to meet her. I didn’t know it yet, but when she heard that I was in Malaysia she’d had a plan for what I could do there.
She works at an international school in Kuala Lumpur making costumes for the theatre department. When I arrived, she’d taken a freelance job doing costumes for a play about the life of Napoleon Hill, and they were looking for actors.
She brought me to a rehearsal to meet the director, I think knowing that he’d try to recruit me. When the director heard my deep voice he decided almost immediately that he wanted me to play a U.S. senator, despite the reservations of some others due to me literally cowering in a corner for the whole rehearsal given how uncomfortable the whole situation made me.
When he asked if I’d join the cast I said I’d think about it, and I sat down in the corner watch the rehearsal. My first plan was to be as vague as possible for as long as possible about whether I’d do it, until they got tired of asking me. I found the idea terrifying - I’d always been very shy/socially-anxious and I couldn’t imagine anything that would make me more uncomfortable than joining the cast of a musical.
But then I realized that’s exactly the point. The fact that it was terrifying was a good thing. I didn’t want to be shy - I hated it - and this was the best opportunity I’d ever have to change that. I told him I’d do it.
We rehearsed daily for the next three months. Besides being some of the most extroverted people I’d ever met the rest of the cast were also some of the most accepting people I’d ever met, so I was never made to feel the odd one out despite that obviously being the case. I was actually surprised how much patience they had while I slowly struggled with the discomfort of what I was doing.
I’d made great friends, and had a lot of fun - that in itself was worth it. But what I’d hoped to accomplish going in was an exercise in practiced discomfort to overcome whatever insecurities made me feel uncomfortable in these types of situations. You can hear Tim Ferriss talk about practiced discomfort below:
^ click photo to play video
It worked. I hadn’t gotten over things completely, but I was a changed person compared with three months prior, and I had laid the foundation on which I could continue to change that part of myself over my next few years of travel. My life would be a in a very different place right now if I’d told the director no after watching that first day of rehearsals, and practiced discomfort has been an important part of my life ever since.
We had months of rehearsals, a flash mob at Kuala Lumpur’s biggest mall, and a few weeks of live shows at the end. It was one of the best experienced I’ve ever had. And Malaysia also changed how I travel. I’d spent 3 months there, which felt like a good span of time, and over the next few years I’d spend at least a few months in each country I visited.
Oh, and I spent some time on the Perhentian Islands with some of the cast, which was awesome, but the musical was the highlight of Malaysia so I’ll stop the story there.
Cambodia
My aunt had always wanted to visit Angkor Wat in Cambodia - but she’s the only one in our family living in Asia so she’d never had the chance. We decided we’d go together after the musical.
Angkor Wat was hot. A heat wave hit during our visit. At first we thought this was a problem because we couldn’t survive outside too long (though we tried anyway), but at the end of our trip when the heat died down we realized that it had been the only thing keeping the crowds away. In our final days Angkor Wat filled with people, whereas until then we’d had the whole place to ourselves.
After visiting Angkor Wat, my aunt headed back to Malaysia and I headed to Phnom Pehn to spend a few weeks catching up on freelance work in cafes; Brown Coffee in Cambodia is still one of my favourite cafes in the world.
A few weeks later, after I’d spent the entire time in Phnom Pehn working, I had one day left. I took the day off to walk across the city, one side to the other. When I got to the other side of the city I wanted to keep going, so I kept walking into the villages on the outskirts of the city. There, standing on a dirt road surrounded by farmer’s fields, a monsoon rain started pouring on me.
I started walking back to the city in the rain to hide under overhanging roofs and ledges, zig zagging my way back between different shelters on my way into the city. I was hoping I could find a tuk tuk once I made it back. But, once I made it back into the denser part of the city the rain got even heavier. I was forced to hide under an overhanging roof in knee-deep water for a few hours, in a small street on the outskirts of the city. It was actually fantastic.
Kids were playing in water that was gushing from storm pipes, people were washing their clothes and playing with their children in the rain, and anyone not playing in the rain was hiding under an overhang beside me. I stayed there a few hours enjoying the experience and thinking about books I wanted to write when I’m old and retired.
^ click photo to play video
Once the rain stopped I managed to find my way back to a place where I could get a tuk tuk - it turns out there were a few tuk tuks a few blocks away the whole time - and made my way back to my hostel to dry off. The next day I was headed for Japan.
Japan
Southeast Asia-living is pretty cheap so by this time I’d banked enough money to visit somewhere more expensive. I had always wanted to go to Japan so I had booked myself a ticket the same time I’d booked my Cambodia tickets.
I wanted to continue pushing my comfort zone in social situations, continue to practice discomfort, so when I arrived in Tokyo I signed up for Hip Hop class. But it turned out that this really didn’t make me feel uncomfortable anymore, so I had to move onto something else.
^ click photo to play video
I got to do a lot of cool things in Japan, some friends took me surfing and I went back to my random-walking routine and I got to visit a friend from high school, but the real highlight came with a trip to Okinawa.
Okinawa’s got two groups of islands. There’s the islands around Naha, that’s where Mr. Miyagi’s from and I call it Japanese Hawaii since it’s pretty touristy. Then there’s the group of islands around Ishigaki - it’s far less touristy - you can think of it as a collection of tropical Japanese islands which each have a tiny Japanese town on them, surrounded by untouched coral reefs.
This was a very, very good trip. I think the main highlight was staying in a guest house owned by a guy named Yoshi - everyone staying there had met each other, and Yoshi’s father came to visit the island one night bringing with him a traditional Japanese instrument to play for us. Eventually Yoshi decided to take us all out in the boat to swim the reef under moonlight. Okinawa was a chain of great experiences just like this.
Korea
After Japan I headed to Korea, with no plan what to do when I got there.
I rented a place near Seoul station and settled in for a 3 month stay. A few weeks in I’d gotten over the initial excitement of how good the wifi and the cafes were, so I decided to find something to do. Summer intake for Korean Language programs was happening, so I figured why not learn Korean. I became a student of Korean language at Sungkyunkwan University.
I’d always been interested in languages - I’d learned everything from French to Icelandic while in high school - so I knew I’d enjoy the class. But I was really just hoping to make some friends, which is exactly what happened. The school paired us up with local Korean students studying English, and I spent the next few months exploring Korea with these friends. It was pretty awesome how much effort they put into showing us the country.
After the program finished I spent a few weeks in cafes catching up on freelance work and hanging out with some friends. I took a trip to Busan, where I would walk as far as possible in a random direction like I’d done in Thailand. I’ve been back to Korea for 1-2 day trips here and there since, but I really want to spend more time in Korea someday.
Taiwan
I’d gone to Korea because it was the closest flight form Japan, so I followed the pattern and headed to Taiwan next. I’d had a Taiwanese friend Ray in my Korean class, so I figured I’d have a friend there as well. Within a few days in Taiwan I met Reynold, then Ian, then Gaetan and we spent a lot of time together over the next few months in Taiwan.
I’m writing this blog post so that I don’t forget about the period of my life I spent traveling - but the one thing I know I won’t forget is why I decided to live in Taiwan, so I’m going to skip putting that in here. That’s its own story. I spent 3 months in Taiwan before heading to Hong Kong.
Hong Kong & Macau
After Taiwan I headed to Hong Kong. I was mostly catching up on work again while here, and hanging out with some friends I’d met, but the highlight of Hong Kong was actually the trips to Macau.
^ click photo to play video
I loved Macau. I went there with my friends for a night (Ian from Taiwan had come over, and introduced Ben). After that I went back to Macau for a day by myself, to explore the city on foot. Up to this point I’d hated taking pictures any time I traveled, but I pulled out my iPhone to take some quick videos as I walked around that day and a few months later edited them together in the video above.
The Philippines
I only ended up staying in Hong Kong / Macau about a month. I cut it short to take a trip to the Philippines with Anna. I’d met her while living in Taiwan a few months before, and when she came to the Philippines she had a plan to bring me back to Taiwan with her afterwards. The entire time I’d been in Hong Kong I’d been thinking the exact same thing, so that wasn’t very hard for her to do. She’s been my girlfriend since the trip, and now (a few years later) I’m sitting in Taiwan beside her as I write this, so I guess her plan worked.
We flew to Clark (a small city near Manila with cheap flights) with the intention of going to Boracay. I asked the taxi driver “how far to Boracay?” and he answered “what? you mean by plane?” Apparently Boracay was in a completely different part of the Philippines. I hadn’t even checked a map before we’d flown there, so with Boracay on the other side of the country we needed a new plan.
We went to Tagaytay where we rode horses up the Taal Volcano where that picture above was taken, explored Manila and headed to Olongapo to see Subic beach, and rode tuk tuks through the mountains.
After Anna left, I stayed in Manila a few weeks while I renewed my passport at the Canadian embassy, working out of cafes and walking around the city. Once I got my passport, I headed back to Taiwan with Anna.
Nepal
I was having a beer with a friend (Ian), talking about how I couldn’t decide where to travel next and he said “my friends went to Nepal in high school, they liked it.” I thought that sounded like a good idea.
I flew into Kathmandu the next week and after a few days walking the city headed into the mountains, to a town in the Kathmandu Valley called Nagarkot which I wrote about here. After some time there I checked where the next largest city was: it was Pokhara, so I got on a bus and headed there. After arriving and Googling “what to do in Pokhara” I stumbled onto something called the Annapura Circuit. It’s a trekking route, generally considered one of the best - if not the best - treks in the world.
It sounded great. I bought a rain coat, packed my backpack, and got ready to head for the Himalayas.
The morning I was leaving my hotel for the trek I saw someone in my hotel (Nadith) reading a brochure for the Annapurna Circuit over breakfast. I asked if he was going to do the trek and he said yes, he was planning to leave a few days later but when he learned that I was headed there now he went upstairs, grabbed his gear, and we headed out on the trek together.
Depending on your route the Annapurna circuit is a roughly 3-week trek through the Himalayas. It passes by some of the world’s tallest mountains, and directly through some of the world’s highest passes. It’s really impossible to describe here in a blog post - you’ll have to go someday.
^ click photo to play video
Nadith and I trekked together for quite awhile, but about half-way through he unfortunately hurt his foot and had to trek his way out to the roads where he could get a ride back to the city.
After Nadith left I set out on my own. Typically the Annapurna Circuit can be a bit crowded due to its popularity, but this was the very end of the rainy season and the tourists hadn’t arrived yet; there were only a few others doing the trek. I’d head out each day alone (which I love), but because everyone was on roughly the same pace I’d end up meeting up with the same trekkers each evening in the next town. We soon had a group of friends. It was pretty awesome to trek alone through the day, then meet up with your friends each night.
^ click photo to play video
I didn’t trek the whole way alone. Once we reached the Thorong La pass we all decided to go over together as a group of about 20 trekkers - this pass is where quite a few hikers died in 2014.
Once over the pass, the town on the other side had hot running water and beer. This was a bit of a shock because the day before we had been so deep in the mountains that there was no electricity save for a few solar panels. I then spent the next few days trekking with a group of Germans studying in Thailand (hopefully I can visit them in Germany someday), then again set out on my own when they settled down for a rest in Kagbeni.
But as I trekked, I kept running into people I’d met along the way each evening, and I’d even end up meeting up with the German group back in Pokhara after the trek.
The Annapurna Circuit is too diverse to fit into a blog post. You’ll trek through jungles, snowcapped Himalayas, Buddhist templates, deserted plains neighbouring Tibet, mountain-top lakes and waterfalls, and far more than I can list. I will probably do it again someday.
Biking the West Coast of Taiwan
Typically in Taiwan I’d have a weekend trip or two, but I mostly stayed in the city. A big exception happened between Nepal and Sri Lanka trips where I took a bike down Taiwan’s west coast for a few weeks. I’ve got that here.
Sri Lanka
I went to Sri Lanka for a few months to learn to surf, and booked myself into a beach-side hotel on Sri Lanka’s southern coast. I’d surf a few hours each morning, then work on my laptop in the evenings, hoping to finish up all of my work so that I could take a few weeks off.
^ click photo to play video
The waves were a bit rough, and when it finally came time to take a few weeks off work I decided I needed a change of plan. Someone in my hotel had rented a motorcycle - it seemed like a good idea, so I rented a scooter and planned to drive it right around the whole island of Sri Lanka.
As a sidenote when I got to where the scooter rental was I realized that that was where the beginner waves were for surfing - the rough waves were because I was in the wrong place. So someday I plan to go back to these beginner waves and learn to surf.
Anyway - I jumped on the scooter and started driving off into the depths of Sri Lanka. I didn’t have a map or a data plan on my phone, and very few people outside the tourist areas spoke English, which made everything a lot more fun.
^ click photo to play video
Sri Lanka’s a pretty amazing place. It’s got amazing beaches, huge deserts, beautiful mountains…and what seems to be what most people imagine as African wildlife. I first headed to Sri Lanka’s South-East Coast where I checked into a hotel in the middle of a rice field (shown in the video above), then headed out on Safari to see elephants, leopards, and more of the local wildlife.
^ click photo to play video
After the safari I got back on the scooter and headed north into the mountains. I drove through Kandy where I almost got arrested for not having a license, into Nuwara Elia and Ella through mountains covered in tea fields, then back down into the plains to head towards Sigiriya.
I remember getting caught in a more than a few downpours and hiding out in the biggest trees I could find; I remember following signs for a local temple down a steep dirt road and almost not being able to make it back up the slope on the way out, getting stuck deep in the Sri Lankan forrest as a result; I remember winding roads through tea mountains, and getting lost on roads so remote that kids would get so excited to see a foreigner they’d chase you down the street to wave.
^ click photo to play video
When I set out I had planned to circle the whole island, but I had been almost two weeks on the road to make it to Sigiriya, so it was time to turn around. I took the route through the capital Colombo on my way back south, relaxed a few more days on the south coast, then I took a train back into Colombo before heading back to Taiwan.
^ click photo to play video
What I’m Doing Now
I’m not done traveling - since going to Sri Lanka I’ve visited India a few times, I’ve been back to Japan/Thailand/Malaysia a few times, spent a few weeks in a Changzhou, China, I hop back and forth with San Francisco, I took a train coast-to-coast in Canada, and just recently got back from my first trip to Shenzhen. But I’m in a different phase of my life now. My Sri Lanka trip was over a year ago and my life’s focus has shifted from full-time travel to building our business. For this past year I’ve been wanting to document this phase of my life so that I can look back on this years from now. I’ve finally been able to do that.
Red dirt overlooking Taichung city.
] Taken while standing inside a giant Buddha.