TLDR: I took a one-way flight to Japan to see if I could run my two US corporate jobs from a 150-square-foot hotel room. It worked better than I imagined.

I have an Ivy League degree and an MBA from a top-7 school, but my most valuable education came from a Japanese business hotel chain. It taught me that we are thinking about remote work all wrong.

My past few years living in Asia started with a benign post-New Year’s whim.

After college and b-school, I was running a hybrid J1 at a big-name consulting firm and a remote J2 boutique firm. To be honest, my J1 had essentially become remote; the team was scattered across geographies, and no one cared where I was.

So, I booked a one-way flight to Tokyo from North America.

I thought it was a small and fun risk to take. I’d do a week of planned vacation, then just.. not leave. I’d work a few days from Japan, on flipped hours and see what happened.

Worst case, I’d book a flight home. Best case, I’d get an extra weekend in a country I’ve always loved. I’ve been a closeted turbo weaboo and even took a couple of semesters of Japanese in college. This was already my 4th or 5th trip to Japan; instead of being a tourist, I thought that I’d run an experiment.

Before I left, I did some basic operational security. The key is to not install commercial VPN software on your work laptop (like ExpressVPN, NordVPN, etc.). Instead, I set up a private VPN server on a cheap travel router. All my traffic was piped through a private US IP address before the data touched my work machines.

I landed and checked into an APA Hotel. If you’ve never been, they’re a chain of no-frills business hotels across Japan popular with business guys and budget-conscious travelers. Super tiny but efficient and clean.

I had three laptops—J1, J2, and personal—and I’d be hot-swapping them on the single small desk, keeping the others on my bed. It was a tight fit. ☹️

My workday started around 11 PM or midnight Japan time and ran until 8 AM. At first, it was disorienting. I’d finish my day as the sun was coming up, grab some breakfast from the Lawson (convenience store) inside the hotel, and then go to sleep.

I would go out in the middle of the night for ‘lunch,’ which usually consisted of some derivative of gyuu don (beef bowl), which luckily happens to also be my favorite food.

The first week surprisingly went without a hitch. Granted, I was pretty anxious about the whole experiment, but with no issues, I decided to keep going another week to ‘up’ my weaboo power level (this was also during a time that I’ve become somewhat fluent in Japanese up to almost a working proficiency after years of spamming anki vocab cards for a year).

I kept extending my stay by one more week. Then another. I had a flexible ticket, and changing departure dates didn’t change anything.

I ended up staying for two months on that first trip. I visited over 20+ different APA hotels across the country. By the end of the year, I had stayed over 100 nights at this chain and became one of their highest-tier loyalty members. I was living a completely parallel life that my colleagues had no idea about. I ended up going back and staying a lot longer than my first trip.

This is where I think some digital nomads get it wrong. They quit their jobs to travel, trading income for freedom. The Overemployed nomad doesn’t have to choose. You can have both. While they’re trying to freelance their way through hostels, you’re stacking paychecks from a luxury condo in Bangkok.

Thanks to a weak yen, my US dollars also went incredibly far. A recent analysis shows that the cost of living in the United States is over 64% higher than in Japan. My US rent was essentially the nightly rate of a business hotel, and my food costs were a fraction of what I’d spend back home. For me, I was also getting the language immersion that really boosted my fluency. I don’t consider this a fun travel hack. Rather, I think it’s geographic arbitrage, that has been made possible in our new form of work in the age of remote and AI.

There are over 18 million Americans who call themselves digital nomads, but I think most of them are leaving money on the table. They aren’t leveraging their existing, high-paying corporate jobs. They’re starting from scratch. You don’t have to.

I eventually left Japan and now I’m running the same setup from a condo in Bangkok. The principles remain the same. My jobs are in North America, but my life is in Southeast Asia. I don’t consider myself an elephants-pants wearing, espresso-sipping, meditation-practicing foreigner in search of the exotic. Rather, I still consider myself operating at the same level of intensity as during my ivy league and business school life but just in an environment that challenges me to think differently and view my life through more ambitious lens.

It’s about fundamentally redefining the relationship between work and life. This is the freedom you’re actually working for. It’s about having the leverage and the operational security to build a life where your physical location is a choice.

The biggest benefit of OE isn’t the money. The money is just a tool. The real prize is autonomy. It’s the ability to look at a map and decide where you want to be, without asking for permission. My time in that tiny Japanese hotel room taught me that the future of work isn’t about being remote—it’s about being free. I go into more detail about how I got started on this path in another post. You can check out my article on how I fell into OE here.

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