The PanAmerican Ride: Prologue – March 2012 to August 2015 – “when you’re finished in Thailand, I need a partner”

“When you’re finished in Thailand, I need a partner.” The Pan-American highway ride, from Alaska to Argentina, began with nine words. AR and I had ridden to Cambodia and through northern Thailand together, sharing a sense of adventure and romantic travel ideals. Our first Christmas in Thailand we’d kayaked to camp on a tiny little coastal island, where we sang Christmas carols around his tiny battery-lit tree. In Angkor Wat, we’d taken turns posing in a brimmed hat in the ancient temple, our own Indiana Jones pictures. We’d shared completely impractical, improbable adventures, and loved them. And he had an idea for another.

“I finally bought my new motorcycle,” he wrote from Canada, “I need a bad-ass partner… we go south in Mexico, and you can finally teach me some of that goofy dancing you love…we would keep going down into Guatemala…El Salvador to Honduras, Nicaragua, Costa Rica and Panama. But to stop there would be just silly, you see? Colombia is just a little further, and then there are just so many options…we end at the southern tip of Chile…Let me know what you think.”

“Construction of Japanese bicycle requires great peace of mind”

Reading his letter changed my life. I wanted to go, not least because of the enchanting  hand-drawn map. He and I were born for another century, but we would make the most of our own. I agreed. I would ride a motorcycle to the bottom of South America; I just wasn’t sure when or how.

“How” took two years of work. I was an English teacher when The Letter came. I figured that the whole trip required three months of decent riding and, even camping and eating at taco stands, would cost about $10,000. But that was more than half my salary.

ParadiseIsNowhere – One of our Chiang Mai motorcycle trips


I quit teaching, moving to Chiang Mai to work online, to start a business that would allow me to save for the trip, or at least allow travel and work at the same time. It worked. And I was also lucky enough to spend time with my old college friend, Chavez, and another digital nomad, JP.

I tested my dream, spending three weeks motorcycling the length of Thailand, confirming that, yes, I loved that lifestyle. I also asked my long-term girlfriend, Nin’ta, to join. Rather than a 3-month tornado, I decided to spread the trip over 9-12 months, and spend time working along the way.

We didn’t leave for another year, though I was very tempted to start early and alone when I first rode my KLR650, the one I purchased for the trip that summer. I sat at a stop light one day pointed south, thinking, “my laptop is on the back, I have clothes with me: I could leave right now, just keep driving south till the land runs out.” (My grandmother, a major anchor in my life, had just passed away, so perhaps I can be forgiven for wanting to run away.) My story would have been very different if I had kept driving that day, but I’m glad I didn’t, glad I was able to share my travels with Nin’ta, even when we were at odds, and glad to have had the trip that I did.

For the beginning, Chavez and another friend, RJ, decided to join. Chavez was the one who decided that there was really no point in starting the trip from Colorado, when the road started up in Alaska. His logic was unassailable; Alaska seemed like a small add-on to an already large trip. Nothing wrong with an extra couple weeks of travel – it would be quick, right?

ParadiseIsNowhere – Pan American Plan – obvious now, adding Alaska was decidedly not quick

In the end, the Pan American didn’t take just one year. Or two. I’m writing now 3 years after we started, and only off the bike for a few months.
We met many riders along the way with the Tierra del Fuego (southern Argentina) goal. Only a handful made it all the way. None took as long as we did. Instead of trying to get to the bottom as quickly as possible, we lived in countries along the way, spending months without even starting the motorcycle, getting to know foreign cities as home.

I’ve forgotten so many details from the trip, I know there are people we met who are lost in time, and texture to the days and stories I won’t be able to recreate, not even from the thousands of photos and the old journal entries. (And even those are less than they should have been, due to a journal getting lost by FedEx Colombia – more on that frustration later). But for my later self, for the kids we may one day have, or for anyone out there who wants to make the same trip, even if it’s just by armchair, here’s my Pan-American travel story.

Dedicated with love to AR, who is about to start the Pan-American trip he inspired me to ride, and to Nin’ta, my partner in our crazy, adventurous life.

passive, whatever that means

I’ve decided my next step involves passive income. This summer was tough, financially. And it’s still tough. I’ve been looking at finances and while I’m still floating, I need to land some serious work over the next few weeks to keep that state. At the same time, when I ask myself what I really want, the first answer is always travel, adventure — things that don’t come easily while working.

I’m incredibly grateful for the work I’ve had over the last few years. Looking back at the beginning of my freelancing and the goals from that time, this has given me so much more freedom and financial reward than I could have expected four years ago. That we were able to live well all the way through Latin America while staying in decent hotels and beautiful apartments — I’m incredibly grateful.

But I’ve also known that coming back to Chiang Mai wasn’t an endgame goal, just a stop along the way. I’m glad now to have a home and stability, and looking for a balance, but I also know that my current situation is too tenuous; I want to be able to travel for a few weeks, or take off some time to help with my family, and not feel like I’m risking my financial future. The only way I can see to achieve that is to create passive income.

A few years ago I read a great article on that subject on the Steve Pavlina blog. The guy has some weird ideas about some areas (his open relationship series isn’t for me), but he does have some great psychology regarding starting a passive income source, so I’m going to be following along with his series on creating your first passive income stream. I don’t know exactly what that will be, but I do know the first step: creating a goal.

Passive income goal: $100 per month in passive income by April 13th, 2019, my 35th birthday. Stretch goal: $1000 per month in passive income by August of 2019, one year from now.

Interestingly, looking back on my old posts as I imported them from wanderlustadventurer, I was struck that my freelance business started almost the exact same way.


Amp joined me in one of my regular coffee shops, and laughed as she told me that the staff thought I always looked “so serious”. I’ve caught sight of myself in windows while I work, and they’re right – my neutral expression when I’m working is intense, furrowed, and definitely unfriendly.

That was a few years ago, and I’ve been working on being more approachable since. On Saturday, I had several random strangers approach me and start up conversations, and I thought, “Win!” Today I realized I may be too approachable.

Sitting at a small outdoor mall watching people walk past, I was surprised when I Chinese woman came very close and asked me where I was from. A group surrounded her, from little round-faced children to older retirees, and they seemed so damned excited about my answer. The leader showed me a question on her phone, asking me to help them with a game. I said “sure, I guess” – and the group actually clapped.

They told me to repeat a short phrase in Chinese, and with my year of living there, copying the sounds was easy. They clapped again! This is great! I have no idea what’s happening!

Then they motioned me to follow them, and I walked to the front of the shopping area, where I saw no fewer than five high-end cameras with oversize fuzzy microphones all pointed at me, recording, and the woman asked me to repeat the phrase I had just “learned”.

But… I can parrot almost anything with a decent ear for language, but my memory for language is essentially nill. I don’t think them recording me saying, “I don’t remember,” in English was quite what they were hoping for. But it’s what they got.

Gamely, they still gave me a keepsake… keychain? Window pull? Curtain tassel? A keepsake. We’ll just call it a keepsake.


Goal! I was just researching some info on fitness, and opened up the settings of my food tracker (SHYE, See How You Eat) to make a note, when I saw the goal I’d typed in months ago: 34″ waist size at 200 lbs. When I downloaded this app, I weighed about 225 lbs (down from my all time high of 243 lbs), and had a waist of somewhere in the 38 inch range. Since then I’ve been steadily losing weight, but like most goals, I like to shift the goal post as I go. Last week I noted with some discouragement that my waist was still 2 inches more than I’d like, and I recently decided I’d like to lose an additional 15 lbs. I’m hard on myself. I was discouraged.

But opening up this app, I realized how far I’ve come: my waist measurement was 34 inches last week, and my weight is now below 195 lbs. Without even realizing it, I’d already passed by my old goal.

Wednesday Weekly Update: Sick!

We said goodbye last week, my sister and nephews hugging us tightly before walking the winding queue through security, and disappearing beyond. I miss them – funny how quickly you get used to having family around, how lonely it suddenly feels when they’re gone.

But at the same time, I was looking forward to some rest. This summer has been almost excessively busy – like a proper summer should be! – and now, I thought, would be a great time for catching up on work and resettling in Chiang Mai. Instead, we spent the week in bed sick.

I’d started getting a cold on Monday, and by Wednesday it was in full swing. I tried working a couple of times, but felt incredibly stupid, like I was using an underpowered computer. “First I click here [pause] and then I’ll need to [pause] yes, add that feature to the model there [pause] and then I’ll [pause] fuck it.” On Friday I sent a series of hurried and apologetic emails to clients; gladly, I received only kindness and well-wishing in return.

Luckily, Saturday I was starting to feel a little better, and wanting to get out of the house, hoping to clear away the cobwebs before Monday arrived. We’ve been enjoying the MoBike hubless bike share here, and so we grabbed a couple bikes to head to the university grounds and explore.

We’d been to the arboretum before, but a group of volunteers happened to be painting, and we got to see the fitness equipment in transition to their new, cartoon-animal selves.

For lunch we headed to my current favorite restaurant in Chiang Mai, Sushi Umai. The sushi is spectacularly good, but I come in equal measure for the quiet I find there. The staff is always friendly and welcoming, the interior has a pleasant hush to it, and a TV plays NatGeo on low volume, usually showcasing international eats that whet both my appetite for the delicious maki and sashimi I order and for more travel. It suits me, and I go there as a sanctuary, stepping into the softly lit interior like timeless prince into a fairy ring (Zelda fans know what I mean).

Sunday we woke with little energy; Amp had picked up my cold, and we mostly hung out at home. Monday I was able to get a little work done; Tuesday and Wednesday I was tired again.

However, I have decided to try setting aside a middle day each week to explore business opportunities, and Wednesday I wandered the large Worarot Market near the Ping River in search of silicone nylon to make outdoor and travel gear. A helpful cloth merchant was willing to point me in the direction of another cloth shop and even wrote down the name of the material I wanted in Thai for me, but though I found that shop, and stopped in at a dozen others asking for the material, I had no success. I don’t think silnylon is available here in Chiang Mai, which casts serious aspersions on my dreams of manufacturing outdoor gear here. Not losing hope yet, though — may be able to find something in Bangkok.

More next week, I hope. -Ch