This is not entirely travel related, but it’s something I’ve been meaning to write. In March of 2020, I moved to Japan, right before the coronavirus pandemic really hit either Japan or the United States. Moving here was something I’ve intended on for a long time, and I maintain that it was one of the best decision in my life, despite complications from the pandemic. This will be a multi-part post, from the background motivations, to the processing moving there, and then practical tips for others making the move.

My love for Japan started in college. I had gone on a graduation trip to Japan in high school with my family, a few relatives, and some close family friends. We went with an Asian tour group, and went around various cities in the Kansai region: Osaka, Kyoto, Kobe, and Nara. I definitely enjoyed that trip, but at that point in time I spoke not a lick of Japanese, and I just viewed it in the lens of stereotypes: a foreign place with strange and interesting customs, with delicious food, cleanliness, polite people, and a mix of storied traditions and hyper-modernism.

My roommate in college from sophomore to senior year was a second generation Japanese-American, but totally fluent and also a big fan of anime and manga. By osmosis I also picked up a love for anime and manga beyond the casual exposure from growing up in a fairly Asian environment in the San Francisco Bay Area. By senior year, I started taking Japanese language classes. I even helped my roommate move into Japan after he graduated! I also started to appreciate my Taiwanese heritage a lot more around the time I entered college.

I continued taking Japanese in graduate school, but in a less intense capacity as I had to focus on graduate studies. More importantly though, I started volunteering on the urging of a friend for the Stanford Japan Exchange Club (or SJEC), an exchange program bringing Japanese college students from various colleges (Keio, Doshisha, and Kyoto University) to Stanford for a month, where we would expose them to American college life, and show them around California. These were some of the happiest and most meaningful memories of my life, and I continued helping out with the program for 6 years, even after graduating with my master’s.

I became close friends with many of these students, and as I entered the working world with a job that allowed flexibility in travel, naturally I started to visit Japan and my friends there, along with other countries in Asia. I think I knew fairly early on that at some point I wanted to live somewhere in Asia, as I believe Asia is the future, but didn’t know how. I kept up my Japanese lessons and the frequency of my visits started to increase, from 1 time a year, to 2 times a year to 3, and finally 4 times a year before I eventually moved over.

Every time I came, I would marvel about how amazing the lifestyle and everything was in Japan. I knew about the darker sides of Japanese work culture though, and maintained that Silicon Valley was still the best place to be for a tech career. But was that true? Was there a way to maintain Silicon Valley levels of compensation, benefits, and work culture, while living in Asia?

I had a list of candidate cities I wanted to live in, from Seoul, Hong Kong, Shanghai, Singapore, Taiwan, and Tokyo. I do have a fondness for Korea, so maybe Seoul, though tech jobs would be more prevalent in Tokyo or Singapore. Hong Kong is super interesting and it’s a place I used to love visiting, despite being a bit small. But there aren’t that many tech jobs that aren’t in finance in Hong Kong. Shanghai is a super cool city, though I’m not super comfortable in mainland China. Singapore is fun and really modern and clean, but a bit small and very hot all the time. As a Taiwanese-American, Taiwan has a large amount of attraction for me, but jobs there aren’t great compensation wise and it is also hot all the time. Taiwan might be good to start a business in though. But in my heart, I wanted to move to Tokyo. It’s my number one favorite city, with an endless expanse of interesting things to do and amazing food. Plus, I figured it would be good to get my Japanese fluent first before moving onto any other country in Asia. By 2016-2017, I was pretty much decided on moving to Tokyo.

From research, what I had heard, and my experiences visiting Japan 24 times before finally moving, I knew that I meshed well with the lifestyle here, but that it also wasn’t the perfect ideal place. Japan has its own set of problems, including an aging population and slowing economy, discrimination in various forms, bureaucracy, and an intense work culture. Furthermore, it would be easy to stay within the expat bubble if I didn’t make an effort to learn the language and meet native Japanese. So I wasn’t coming in as an idealist who would have his illusions shattered. However, finding the right job, looking Asian, having a good handle on the language, and being patient and tolerant would negate most of the negative aspects.

But how to get there? At that time, I was working at Dropbox. We had an office in Tokyo that I visited a few times. I floated the possibility of transferring to that office, but that was rejected. I ended up leaving Dropbox in January of 2019, partly because that wasn’t a feasible avenue for moving, and partly because 4 years were up and I had vested the majority of my stock.

Here is Part 2, on how I found a job and moved to Japan!