I often get asked how and why I’m living in Tokyo. When I was younger, I never thought I would be living in Japan, especially as a full-time resident. In this post, I’ll share my story about how I ended up in Japan, my thoughts as a foreigner who can’t speak Japanese, and my plans for the future.

I was born in Hong Kong, and grew up half an hour north of Boston. Since high school, I had always wanted to visit Japan. I blame some of my fascination with Japan on Pokémon, but I was also very interested in Japanese industrial and product design. Compared to other teenagers, I did a lot of traveling in the form of family vacations to Hong Kong. The only other country I visited with my family was Thailand. Other than that, it was always Hong Kong. Alas, I never got to see Japan until much later in life.

A family vacation to Hong Kong.
One of my many family vacations to Hong Kong.

In the summer of 2015, I spent three months working on The Dai Show in Xishuangbanna, China. It was an exhausting, but fun, experience, and I got to work with a few of the world’s best sound designers, lighting designers, and more. Here’s one of my favorite photos from the show.

The Dai Show in Xishuangbanna, China.
One of my favorite moments in The Dai Show.

Visiting Japan for the First Time

After a successful show opening, I flew to Hong Kong for some much needed R&R. A few months later, I visited Japan on a whim. My good friend Jeff happened to be in Osaka, so I flew over to spend Christmas with him. Here are a few photos from my first trip to Osaka – very memorable.

A few days later, I took the Shinkansen to Tokyo, and met up with my friend Simon who was there for a business trip. I didn’t get to see much in Tokyo because I was only there for two days. I visited the usual spots like Asakusa, Shinjuku, and Harajuku, and spent most of my precious time eating. At the end of the trip, I was sold on Japan. Before my flight back to Boston, I booked a multi-week trip to Japan for the following summer.

Sensō-ji in Asakusa.
My first visit to Sensō-ji in Asakusa.

Six months later, I was back in Japan with my brother. In addition to visiting Tokyo and Osaka again, we also made stops in Kyoto, Hakodate, Sapporo, Biei, and Furano. Here are a few photos from that trip.

I won’t bore you with the details from this trip, as that is not the point of this post. Needless to say, it was lots of fun. Over the next two years, my life/work situation allowed me to do a lot of traveling. I took advantage of the situation and visited many countries including Singapore, Austria, South Korea, Germany, United Kingdom, and of course Japan.

During my travels, I realized I didn’t want to live in the USA anymore. I don’t have anything against the USA. It’s a nice place to live, and my family is there. I just wanted a change of scenery. So, I moved to Japan because I wanted to see more of the country. Oh, and also because I fell in love with a girl.

Moving to Japan

So, in January 2018, I showed up in Japan with a tourist visa after quitting my job, hopped around various Airbnbs, and started my new life. Contrary to popular belief, I had absolutely no idea what I was doing. I couldn’t speak Japanese, and my purpose for being in Japan was so I could walk around, see cool places, take lots of photos, and have fun. Sounds spoiled, right? Wrong! I worked my butt off for two years, and I needed some serious relaxation time.

Now, you’re probably thinking how I was able to just show up in Japan without any plans or job. I think it’s fine to not have a plan, but moving to a new country without a job or interview lined up was definitely a little reckless. As crazy as it sounds, I was able to move to Japan without a job because I had a few income streams – affiliate commissions from my blog, occasional sound design freelancing work, and the cryptocurrency bull market in last 2017. Between those three income streams (mostly the third one), I was able to kickstart my adventure in Japan without taking an office job or English teaching job.

Life was pretty great. I spent my mornings and afternoons walking around Tokyo with my camera. In the evenings, I’d meet up with my girlfriend (now wife) for dinner. On the weekends, we took day trips to Hakone, Fuji, Kamakura, and other beautiful places in Japan. I really loved the lifestyle because it allowed me to focus on turning my various hobbies into income streams.

Day trip to Mount Hakone.
A day trip to Mount Hakone.

Settling Down in Japan

In the summer of 2018, I got married with my now-wife after she got pregnant. In my long history of unplanned situations in life, this took the crown. We both had literally zero plans to become parents at 26. I don’t want to turn this post into a debate on politics and ethics, but we’re both firmly against making selfish excuses like “but we’re not ready” and killing a life, so we decided to keep the baby. It ended up being one of the best choices we ever made.

The cutest baby you'll ever see.
The cutest baby you'll ever see.

After my now-wife found out she was pregnant, our lives suddenly mattered. When I say “mattered”, I mean it in the sense that we’d be responsible for keeping another human life alive very soon. I certainly can’t say I have experience with that level of responsibility. We spent the next 4-5 months preparing. It was a lot of preparing. We got married, moved to a bigger apartment, decided on a name, figured out how dual citizenship works nowadays, bought and assembled furniture, researched about everything we could think of – the list goes on and on.

We also decided it would be best for me to get a job. Relying on freelance work and trading crypto doesn’t exact scream “financial stability”, especially with a baby on the way. Between June and October, I shifted between two companies. The first role was a remote marketing gig at BigPay. The particular project I was assigned to ended up folding in a few months, so I quickly became unemployed again. While searching for another job, I was offered a content writer position at Liquid Global, and I did that for a while in addition to my other freelance work.

Visiting teamLab Planets in Tokyo with my pregnant wife.
A month and a half before the little guy above was born.

In November, I was hired by Kinsta for the support engineer position. I’m still at Kinsta today, and I will be moving to the marketing team in a few weeks! Being able to work at home allows me to spend time with my wife and baby. In Japan, where salarymen work unreasonably long hours, I really consider my current work/life balance to be a blessing. By the way, we’re always looking for new talent at Kinsta. If you’re interested in a fully remote position and love working with WordPress, check our our careers page.

I’ve been living in Japan for almost two years now, which is much longer than I had anticipated. The original plan was to spend 5-6 months traveling around Japan before deciding what to do next. Life proved once again that plans don’t always pan out the way you expect them to. At this point, we’ll probably spend 1-2 more years in Japan. After that, we are planning on traveling around the world as a family for a year before coming back to Japan for kindergarten.

What’s it Like to Live in Japan?

To wrap up this post, I’d like to share a few pros and cons of living in Japan. These are my personal opinions, and are highly reflective of my personality and current work, life, and family situation. Also, I’ve only been living here for a year and a half, so I’m sure my perspective will be very different in the long term.

Pros of Living in Japan

  • Tokyo is very safe and the variety of transportation options is convenient. I’ve never felt remotely unsafe, and that’s a welcome change after living in uptown Manhattan and Las Vegas.
  • Tokyo is fairly English-friendly. As an American living in Japan, I don’t feel disadvantaged in day to day life. With that said, one of my goals in 2020 is to learn more Japanese so I can communicate better with my in-laws.
  • Living costs are affordable. I was always running low on money when I lived in New York City. That doesn’t seem to be the case in Tokyo.
  • Japan is extremely photogenic, and that’s great for me because I love taking photos. Check out my Instagram if you want to see some of my photos.

Cons of Living in Japan

  • Making new friends has proven to be difficult. Since I work at home, I don’t have the opportunity to engage with colleagues in real life.
  • Everything administrative task requires paperwork. Thinking about the amount of paper that is being wasted on a daily basis makes me nauseous.
  • I understand the cultural notion behind high quality packaging and presentation, but the degree of plastic usage from a practical standpoint is an absolute environmental disaster.
  • Witnessing droves of exhausted salarymen is exhausting in itself. I hope Japan’s horrific work culture will improve someday.

In general, I really enjoy living in Tokyo. I think it’s the best place to live in Japan for digital nomad types like me. If you’re moving here for an office job or English teaching job, I think you’d still have a good time – just be prepared for the terrible work/life balance. If you have any questions about living in Japan, please reach out to me on Twitter or send me an email.