Next up in our Impressions of Tokyo series, we hear from Anne and Tyler, a pair of digital nomads who have taken living, traveling and dating to the next level. Read on as the couple shares the (mostly) ups and downs of their one-year round-the-world trip that includes a stop off in Japan.
A few sentences about yourselves please.
Tyler is a self-taught software developer, entrepreneur and cleantech geek. He is also a connoisseur of backpacks. Anne is a foreign policy nerd, yogini and blogger.
You’re currently on a one-year round-the-world trip, what sparked the desire to pick up and go?
A round-the-world trip has long been a goal for us. We are curious people who are passionate about travel. We talked about a trip like this way before actually committing to it, but I wasn’t quite ready to leave my job. After a few months, I turned in my papers and met up with Tyler in Croatia to begin our trip.
How did Tokyo end up on your travel list? How long is your stay?
We were both intrigued by stories of Japan’s craftsmanship and dedication to excellence. We wanted to experience it for ourselves—especially when it came to craft coffee, cocktails, and food. We stayed for 3 weeks and fell for Japan. Hard. We look forward to returning to experience Japan during the different seasons and see other parts of the country.
Tell us about an interesting moment or experience you’ve had in the city.
Besides trying to figure out how the toilets worked—which was always an interesting experience—we mixed up the date when were to check out of our apartment. Around 5pm, we received a message from our Airbnb host asking why we hadn’t checked out yet and that his next guests were on their way. We hustled back to the apartment, quickly packed up, and left. We found ourselves homeless in Tokyo on a Friday night. Luckily, we happened to be in Dogenzaka—Love Hotel Hill. We decided if we were going to stay in a love hotel, we wanted the strangest one possible. We shopped around for maximum weirdness, but as we looked around, the rooms were selling out… fast! Friday night in Tokyo I guess. We settled on a cheesy, Italian palazzo-inspired hotel complete with marble columns in the room.
Did anything in particular surprise you about Tokyo?
The first thing we noticed is that it wasn’t as expensive as we thought it would be. Hat tip to the TokyoCheapo team for even giving us the idea that Tokyo was affordable, but we were still skeptical before we arrived. We rented an Airbnb apartment in Shibuya for $50/night and ate world-class food for less than $10.
We were also surprised that you could go a whole day without having to interact with a real person. For example, we had several meals where we ordered food from a machine, and either sushi hurled toward us down a conveyor belt at lightning speed, or ramen was slipped to us through a small hole to our individual cubicles. I had never seen anything quite like that before.
Where did you meet? When did you start traveling together?
We met in our hometown of Pensacola, Florida. We grew up in the same place, had mutual friends, went to the same university, but we didn’t meet until three years ago. Our parents even knew each other before we did. In fact, Tyler’s mom was my first ballet teacher when I was three years old.
After Tyler creepily sent me a Facebook message, we went on one date, and then a few weeks later, I invited Tyler on my work trip to Buenos Aires. I was surprised he actually showed up. That was our second date. That began a series of meetups throughout South America. Our third date was hiking the Inca Trail in Peru, followed by our fourth date snorkeling with sea turtles and penguins in the Galapagos. We made our relationship official after that. Travel is a good test to see whether you’re truly compatible.
What do you do for work?
Tyler founded a Micro-SaaS business, Storemapper, which pays his bills and allows him the freedom to live and work from anywhere. He also consults for clean energy companies.
Anne works in foreign affairs in Washington, DC, but she is currently on a year-long sabbatical from her job at the U.S. Department of State.
What’s the biggest advantage/disadvantage of traveling as a couple?
Advantages: Getting to see each other on a regular basis. Disadvantages: Too much time together.
In all seriousness, traveling together has been both wonderful and challenging. You experience beautiful places together, and you learn about each other in greater depth. If you can survive traveling together, you can survive anything in your relationship. It’s the ultimate litmus test. To read more, I wrote a blog post about what I’ve learned traveling as a couple.
How do you strike the right balance between simultaneously working, dating and traveling as a lifestyle?
Balance stems from communicating honestly with each other. Our schedule changes frequently. Some days are spent sightseeing and going into full tourist mode. Others days we hole up in a coffee shop to work. We check in with each other and decide what to do based on how we’re feeling that day. Sometimes that means being alone with each other, and other times that means spending time apart to do our own thing.
What three adjectives/words would you use to summarize your experience of Tokyo?
Bewildering, tasty and komorebi.
Where can we learn more about you, your work and your travels?
Tyler writes about software, energy, and digital nomading on tylertringas.com.
Anne blogs about travel, life and their trip on thetraveldarling.com.
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