The Third Year on the Road: Reflecting on the Highs and Lows

Can we pretend for a minute that it’s late-January 2020 and that the world is still, you know, open?

Because in late-January, when the world was still open and we were still in India, we hit a milestone: our third full year of nomadic life and freelance work. Three years (a little more than that, really) since we’ve called one place home or worked in an office or had more possessions than fit in a few bags.

With every year of this no-longer-very-new lifestyle, being on the road feels more normal and our old lives feel more foreign. It becomes harder to imagine settling in one place permanently or working full-time in an office. Our old homes of Boston and Montana feel more like relaxing vacation spots, and countries like Thailand and Cambodia feel more like places to live and work (it sounds weird, I know).

The Past Year

So, where has the past year taken us?

6 countries: Cambodia, Indonesia, Malaysia, Thailand, Brunei, India

We spent the entirety of these 12 months outside the U.S., first around Southeast Asia and then in India. We kicked off this year of travel in Cambodia, with our third visit to Kampot, where I taught yoga again and we enjoyed settling down for a while in one of our favorite towns. We may have intended to visit some new-to-us countries after that, but we mostly ended up bouncing between our old favorites (oh, hello again, Thailand).

Then last October, we finally left Southeast Asia for India, a place that had been on our minds for so long – and we knew it was finally time. Ryan did an internship in India in 2013 and had wanted to go back ever since, and I’ve been feeling pulled to go there as long as yoga has been a big part of my life. And so that’s where we spent the last three months of this past year.

The Highlights 

In looking back over the past year, the places and experiences that stand out are so varied. But when I think about it more, I realize that every one of them represents something that’s important to us: friends, animals, yoga, nature, and offbeat travel. 

Our Longest Housesit Yet

Most of our housesits over the past couple years have been between one and two weeks, which has sometimes felt like a “long time” to stay in one place. But the longer we’ve been traveling, the slower we tend to want to go – and that makes longer housesits more appealing. They’re also far more competitive, so we were tickled to land a six-week gig in Phuket, which gave us a chance to rest, unpack, and settle down into a comfortable routine.

And honestly? It felt like luxury.

We got to stay in a spacious house with a garden, a pool, and a detached office that I converted into a yoga space. We motorbiked to the local market and nearby grocery stores and cooked our own meals in the fully stocked kitchen. We worked at the house, grateful to have fast Wi-Fi, strong A/C, and comfortable places to sit at our laptops. We walked to the beach, went for bike rides, and took classes at a swanky health resort (our host generously gave us a bunch of free day passes).

And, we got to care for some of our favorite animals yet (not that we play favorites, because we definitely don’t). There was Misty, the pup with a heart of gold – if ever a dog could become a human in its next life, it would be her. Some of our very favorite memories from last year are of walking her along the beach at sunset. Then there was Genghis, the most loving grumpy-looking cat there ever was (and also possibly the sturdiest – he’s not huge, and but he’s shockingly heavy to pick up).

Okay fine, I won’t detail the individual attributes of all four of the other cats. But suffice it to say, we loved having so many furry critters in the house, and those six weeks were like a breath of fresh air (well, until my appendix burst toward the end – you can read that horror story below).

Visiting the “Water Village” of Brunei

Boy did we vacillate about whether visiting Brunei was the right thing to do. We really hadn’t even considered it until a housesit (rather unexpectedly) popped up there. The country’s all-powerful sultan was already a controversial figure, and that was before he famously made homosexuality punishable by stoning to death last spring. But seeing as how we were already in discussions with our housesitting hosts, and that we worry travel boycotts often just end up hurting people who rely on tourism for their livelihoods, we decided to go.

After the housesit, we took a few days to see some other parts of the tiny country. And our short stay in the “water village” ended up being one of the highlights of the whole year. Situated in the river on the edge of the capital, Kampong Ayer is a full-fledged town built entirely on stilts over the water. We’d been fascinated to see the village from a distance, so once we found out about a homestay in Kampong Ayer, we knew we had to make a proper visit.

Staying in a house on stilts, walking the boardwalks between the buildings, taking in the over-water school and fire station – it was a homestay unlike any others. But the family we stayed with – and their generosity and interest in talking with us – was a big part of what made it so special. Like many others, they rely on tourism for their income, and they were eager to show off their country and its culture.

They were also well aware of Brunei’s reputation in the Western world and tourists’ concerns about visiting. Before we left, they told us, “Please tell other people to come to Brunei. Tell them our country is safe to visit, and we want them to come!”

Exploring Some Seriously Under-Rated Places

We’ve always loved visiting places that are quirky, remote, or off the beaten path – places where we can escape the crowds or find something unique and unexpected. And while we often find ourselves bouncing between big cities, ex-pat hubs, and major tourist destinations (chasing housesitting opportunities, yoga teaching gigs, and just convenient places to work), it’s frequently the more offbeat places we remember the most fondly. Especially when we stumble across them unexpectedly.

Kampong Ayer – and all of Brunei, really – definitely falls into that category. But there are a few other places from last year that more than deserve a mention.

Gili Meno, Indonesia

The Gili Islands, a popular side trip from Bali, had been high on our list for years – especially the least visited of the three islands, Gili Meno. Like the other two Gilis, this speck of sand is only a mile or so across and has no motorized vehicles. Unlike the other two, though, Gili Meno is still quiet and undeveloped – exactly our type of place.

Ryan went on a few dives, but otherwise, we didn’t do a whole lot there besides wander the sandy paths and eat at tiny beachfront restaurants. And that was exactly the point. We had high expectations for Gili Meno as a rustic tropical paradise, and I’m happy to say, it delivered.

Ipoh, Malaysia

When we had some time in between housesits in Malaysia, we realized we had already visited most of the country’s main destinations. But as we were researching places to go, we saw a somewhat familiar-sounding town pop up a few times: Ipoh. So, with literally no expectations, we made it our next destination. And you know that? It turned out to be one of our favorite places. We liked it so much, in fact, that we ended up returning for a second visit a few months later.

Ipoh surprised us in so many ways: great food, stunning architecture, access to beautiful nature, and lots of things to do. Not to mention, its fascinating history is on display all over town. Despite all its draws, we saw few tourists and hardly any Westerners there. And honestly, I’m not sure why.

Shimla, India

Another spot I have to mention here – and another one we had zero expectations for – is Shimla. Located way up in the mountains of northern India, it was the first place we visited after flying into Delhi. We already had plans to visit Dharamshala and were just looking for another place we could visit between there and Delhi. Once again, we pretty much decided on Shimla because it was a familiar-sounding name in a convenient location. Fortunately, it turned out to be a great decision.

Shimla just has a great atmosphere. In a country that’s known for being chaotic, this is a place that’s surprisingly peaceful. In the center of town is the sprawling Mall Road, which is miraculously closed to vehicles, making it the perfect place to wander.

When we weren’t strolling around in awe of the architecture and mountain views (or eating in delicious restaurants), we were visiting museums and checking out historic buildings. There’s even a craft brewery (uncommon outside major cities in India), a cable car to ride higher up the mountain, and one of Asia’s biggest outdoor ice rinks (which sadly hadn’t yet opened for the winter when we visited).

Shimla is a super popular vacation destination for Indians from all over the country, but we saw almost no other Western visitors in town. Again, it’s hard to say why.

Seeing Old Friends in New Places

The way it affects our friendships is one of the hardest things about moving around all the time. We’re usually far away from our long-time friends who mostly live in the U.S., and when we meet new people on the road, we rarely spend all that much time together before it’s time to good-bye. So getting to reunite – sometimes unexpectedly – with old (and not-that-old) friends was easily one of the biggest highlights of last year.

As an exception to constantly meeting new people and quickly going our separate ways, we got to be part of a great group of yoga teachers and WorkAwayers when we were in Laos for a couple months at the beginning of last year. And then, by pure coincidence of being in the same place at the same time, we got to see some of our friends from there in Bangkok, and then in Kampot, and then in Bali. Every time, we could not have been happier to see familiar faces.

Then, by another stroke of luck, TWO of my friends from Peace Corps were in Southeast Asia for work at the same time. And since we had just finished a housesit in Phuket before they arrived, we were able to pop up to Bangkok for a way-too-short-but-still-totally-worth-it day together. Even though we live all over the place now, the people from my Peace Corps group are some of my closest friends, and I try to never pass up a chance to see them, even if it requires some totally ridiculous logistics.

Tushita Meditation Retreat

Attending a silent meditation retreat is something we’ve both wanted to do for a long time, but I can’t say the intensity of Vipassana isn’t a little intimidating (although I do hope to do one in the future). So when I heard about Tushita – actually, when I heard about it over and over again from multiple people – it sounded like a perfect alternative.

Located up the hill from the Dalai Lama’s residence in Dharamshala, Tushita is a Buddhist meditation center that hosts different kinds of retreats, classes, and other events. But their most popular offering is a retreat-style Introduction to Buddhism course, which lasts ten days and is held mostly in silence.

We stayed at the center for the full ten days, ate and slept there, and followed a busy schedule of lecture, meditation, and discussion group (the one hour each day when talking is allowed). Housing is separated by gender, so Ryan and I didn’t stay together, and we didn’t talk to each other the whole time.

The retreat was…a lot of things. Informative, eye-opening, challenging, frustrating, busy, quiet. I’m definitely not a Buddhist, but I was really interested in the teachings and how many of them can apply to anyone’s life, and I loved the meditation practices.

I also really liked the experience of living in silence. The whole group (there were about 100 people on our retreat) may have been living, sitting, and eating together, but there was no social pressure, no expectations, and no small talk. And honestly, just the chance to disconnect from electronic devices (they all get put in a storage locker on the first day) and retreat from the outside world was more than worth it.

Diving in the Gili Islands

For Ryan, one of the biggest draws of visiting the Gili Islands was the diving – and those experiences are some of his best memories from last year.

“Combine the coral bleaching that’s happening globally due to climate change with the local practice of dynamite fishing, and you have a recipe for a whole lot of dead coral in the Gili Islands. And without a thriving rainbow of coral and the colorful tropical fish that usually inhabit it, this area might not sound like it has the makings of a top dive spot.

But what Gili Meno lacks in coral, it more than makes up for with its giant green turtles. These massive creatures (they can weigh up to 700 pounds!) were the high point of every dive for me. Most often, they were just chilling on the sandy ocean floor, but every once in a while, they would take off through the water in a whoosh of shell and fins. Just seeing one of these majestic animals is enough reason to strap on your scuba gear.

While neighboring Gili Trawangan has a reputation for being a crowded party-all-night island, Gili Meno feels almost deserted. I went on most of my dives with just the divemaster and maybe one other person, a level of personal attention you’re unlikely to find anywhere else. Trips from Gili Meno visit all the same dive sites as the shops on the other Gilis too, so you won’t miss out on anything underwater by leaving from there.”

The Lowlights

Of course, and as always, there were probably just as many times when things didn’t go well. Some of the most upsetting and difficult things that happened this past year are ones we could easily have predicted – and others are things we would never have considered.

Surgery in Thailand

While the first or so five weeks of our housesit in Phuket felt like paradise, things took a real turn near the end. One night, I started having extreme stomach pain – and the next day, I was being wheeled into surgery to have my appendix removed. I was shocked when the doctor said that’s what was wrong – we all know appendicitis can happen literally at any time to anyone with no warning, but you kind of assume it never will. Until it does.

It was a scary few hours, waiting for tests, waiting for a diagnosis, then mentally preparing to go into surgery. But we were so, so fortunate that things went about as smoothly as they possibly could have. I don’t even want to think about what might have happened if we’d been in another country at the time (the medical care available in Thailand is world-class) or in a rural area, where the nearest hospital could have been hours away.

Instead, I was able to go to one of the best hospitals in Southeast Asia – where the staff speak English, many of the doctors have trained abroad, and frankly the standard of care is better than what you often get in the U.S.

After two nights in a private room (the only kind available) at the hospital, I went back to our housesit, where the animals nursed me back to health. Our travel insurance covered the entire $12,000 bill without much hassle, and I was mostly back to normal within a few weeks.

The Inevitable Illnesses

This clearly wasn’t a great year, health-wise (then again, neither was last year). Appendectomy aside, I also came down with a couple incredibly debilitating colds and lost more than a few days to what I can only assume were run-of-the-mill food-borne illnesses.

And then we boarded the overnight bus from Dharamshala to Rishikesh – a 12-hour journey on steep winding roads. I felt sick from the beginning of the ride, and it had only gotten worse by the morning. When our bus stopped in the larger city of Dehradun a couple hours from Rishikesh, we decided to just get off there to rest, and sort out the rest of our transportation later.

In one of the most unpleasant experiences of my life, I spent the few hours lying semi-delirious in the bus station – believe me, I’ve never been so grateful to be traveling with Ryan. I eventually got up enough strength to take an Uber Outstation (we learned that long-distance ride-sharing is really common and surprisingly cheap in India), and by the time we checked into our hotel in Rishikesh, I figured I was okay. (Narrator: She was not okay.)

I was sick for two full weeks before I finally went to the clinic and got diagnosed with a giardia-like parasite and prescribed some extremely strong antibiotics. I was still sick on and off over the rest of the three months I spent in Rishikesh, and started to wonder if I’d ever be the same again. Ugh.

Our Christmas Apartment Debacle

What do you do for the holidays when you don’t really have a home and you’re thousands of miles away from anyone you know? We ended up temporarily living in Laos over the last two holiday seasons and got to celebrate with new friends there. But this past year, we were on our own.

We’d arrived in Rishikesh a few weeks before Christmas and eventually decided to stay there over the holidays, hoping there’d be something festive going on. As a gift to ourselves – and honestly, in an effort to conjure up some holiday cheer – we decided to splurge on an apartment rental for the holiday week. We planned to relish in more space and comfort, and use the kitchen to cook ourselves a Christmas dinner.

Except when we arrived at the apartment to check in a few days before Christmas, there was nobody there. We asked around, we messaged, we called, we contacted the booking site – nothing. Either the apartment didn’t really exist, the owner forgot about our reservation, or…I don’t know what, honestly. Regardless, there we were, standing outside this apartment building with all our bags and no place to stay that night.

We did get a refund from the booking site, but we were left needing to make a last-minute booking for the week, which meant we ended up paying far more to stay someplace much less nice.

It was a decent hostel in a good location – but it was also possibly the loudest place I’ve ever stayed. Now, Rishikesh is a town with no alcohol (!) and a place where most visitors come to do yoga or attend religious ceremonies. So I’m not sure who went there to party, but they evidently all stayed at this hostel, because there were parties outside our room until 4am every night. Spending Christmas in a loud hostel was a far cry from the apartment we’d planned on.

Accommodations mishaps are inevitable, but the whole ordeal – combined with the freezing weather and horrible air pollution – pretty much depleted the little bit of holiday spirit we were trying to hold onto.

Too Many Flights

The nine flights we ended up taking last year were definitely at odds with our efforts to live and travel more sustainably. Nine flights might sound like a lot to some people and like nothing to others, but it was definitely more than we intended. One of the things we love about travel in Southeast Asia is the relative ease of getting around by land (and sea and especially rail).

But we spent the first two thirds or so of the year bouncing between yoga jobs and housesitting gigs, often without a lot of time to get from one to the next. And flying is pretty much the only way to get from mainland Southeast Asia to Bali, Brunei, or India – so putting any of those spots on our itinerary made flying inevitable.

We saved a lot of time and quite a bit of money (sadly, flying in Southeast Asia is often the cheapest option), but it meant a bigger environmental footprint than we were aiming for. It was also a lowlight because, honestly, I just don’t really like flying – and I do love the train. Fortunately, there are far fewer flights in our plans for this coming year.

Continuing Work Challenges

We are so fortunate to be in a position to control our own work commitments and travel schedules. We have the flexibility to take on (or say no to) new opportunities whenever they come up, we’re able to largely go wherever we want, and we get to decide for ourselves what to do every day.

And this might be our dream life, but boy does it have some downsides. Three years in, we’re still struggling with balance, productivity, and structure, not to mention difficult decisions about clients, projects, and where to focus our efforts. Since we set our own schedules and workload, there aren’t necessarily days off and there’s no such thing as being “done.” And we frequently find ourselves second-guessing whether some new idea will yield results, whether an assignment is “worth it,” or whether we’d be happier or feel more successful if we changed direction.

But these challenges come with the territory of living nomadically and working for yourself, and the only way to handle them is by setting clear boundaries and going all-in on the decisions we make (both things that unfortunately don’t seem to come naturally to either of us). Anyone have some tips for us?

The Next Year

Just after our third travelversary, I spent the month of February doing a 300-hour yoga teacher training in India, and then reunited with Ryan in our hometown. And then…well, you know what happened in March 2020.

When I arrived in Great Falls in March, it was for a two-week visit. We’d leave at the end of the month for an extended road trip through the West and Midwest. We’d do several housesits, camp in state and national parks, and visit friends all over. I’d attend a travel conference and maybe do another yoga training. We’d go to two weddings and to a reunion of my Peace Corps group. We would hit the open road! We would sleep under the stars! We would feel the wind in our hair!

But since I’m writing this in April, I can tell you that almost all of our plans for the remainder of the year have been canceled or postponed. We’ll be hunkered down in Great Falls until all of this is over. And then (whenever “then” is), maybe there will still be some road tripping and housesitting and camping. Fingers crossed.

Have any questions about our travels or work? Post them in the comments!

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