This as-told-to essay is based on conversations with Nick Woolsey, 39, who recently decided to move back to Japan after spending the last six years in the US. Woolsey, an American, is returning on a “highly skilled professional visa” after starting a company that helps people relocate to Japan. The conversation has been edited for length and clarity.
I wasn’t really thinking about permanent residency the first time I moved to Japan, because I was in my 20s and I didn’t really have a plan. Now that I’m in my 30s — soon 40s — I feel like people in my age group need a plan.
In high school, I participated in a very short one-week exchange program with a sister city. Towns and cities in the United States and other places have corresponding cities in Japan, and most of the time, it’s to facilitate junior high and high school exchanges.
When I moved as a college student, I was going to college in Oregon, and they had a great sister school program with Tokyo International University. It was just a six-month exchange program, and then I went back to the US.
Japan Remotely
After college, I did an MBA, and once I finished, I learned that there was a program for being a civil servant in Japan where you would facilitate exchange between your home country and Japan, work with nonprofits, and do translating.
I felt like it was a good fit, so I applied and got in. But when I arrived in 2011, I was placed in a very little town, and they were like, “Nonprofit government management? How about you just go teach English?” And that’s what I did.
Raising a child in Japan was difficult
I was in Japan the second time around for about eight years. I was teaching for two years, and then I met the love of my life — another foreigner, she’s Russian — and she was on a similar kind of work exchange program.
She got a job in Tokyo while we were dating, and she was like, “Are you moving to Tokyo or not?” I said sure, but I just renewed my contract with my teaching position, so she was there alone for almost a year. Then after that, I got a job and moved up to Tokyo and started working in tech.
But kids change everything.
We had our first child in Japan and we went from being completely free doing what we wanted, to caring for this little baby alone in the city. Both my wife’s mom and my parents were really supportive, coming from both Russia and the States to help out when they could, but man, that was bigger than any culture shock I’d ever had.
I was freaking out and I didn’t have any time off from work to adjust to this new reality of having a baby. My wife was stuck home alone. It was a very stressful three months there at first, and we were like, “Do we really want to raise this kid alone in Japan?”
The other issue we had was that we were in the city, so it was very hard to get into day care. We didn’t get in, but there were pros and cons to that because my wife got a great maternity leave — she got two years off.
We stayed for all of that, but in between, we thought about if we needed childcare help from my family. The answer was yes, absolutely, yes. And they weren’t moving to Japan, so we had to move back to the States.
We moved back to my hometown, The Dalles, Oregon, in 2019, for not quite a year before things changed again.
My wife got a job offer at an international startup that had an office in the US, and they asked her to move to Silicon Valley, so we did, maybe six months before COVID. It was also a great financial decision for us to go back to the States because salaries in the US pay significantly more than in Japan.
We were making more money than we had ever made before. We both had jobs based out of Silicon Valley. But in Silicon Valley, we were basically just getting by, because our rent was like $5,000 a month. Preschool was about $3,000 a month, so that’s $8,000 right there with just those expenses.
Most of what we earned went right back out again. So it was then I was thinking, “How could it be possible to have a Western pay, Western work-life balance, but have that quality of life and low cost of living in Japan?”
In the States, recently with how inflation has been going, we would very rarely go out to eat. I went out to some food trucks with my four-person family — and one of them is only one year old, so she doesn’t eat that much — but we had a couple beers, a hamburger, some meat on a stick, and it was $100.
In Japan, you could go as a family to a Michelin restaurant for $100. The scale is totally different, and the quality is totally different.
I think what people don’t realize is that not just Japanese food is good in Japan, all food in Japan is good — except Mexican.
We’ve got French, Italian, great hamburgers, pizza, fried chicken — so many different international cuisines.
Everything that you stop by, even a little hole-in-the-wall is going to be really good. Whereas I felt, especially at those food trucks in the US, it’s like mediocre Asian food, hamburgers, pizza, and tacos.
What’s available in suburbs in the States is limited and expensive, whereas in a small city in Japan, you’ve got lots of international choices.
A high cost of living and a poor job market in the US drove me back to Japan
We did what we could to control our costs. We left Silicon Valley and went to a small town in southern Washington, but costs just kept creeping up. And then there were changes with our jobs, too.
My company seemed like every six months it was going through some kind of layoffs, and I knew my turn was going to come at some point.
That was when I knew that I needed to use my other skills in life to develop a business. And, this is kind of a meta, but I made a business to teach people how to move to Japan on their own terms, because that’s what I wanted to do.
As I was doing that, getting the website all set up and getting my first clients, I got the notice that it was my turn, and my job was going away.
Japan Remotely
And then that summer, my wife and her company came to an agreement that their time together was also finished. We went from two incomes and a startup to just a startup. And that was the point where the golden handcuffs were off. We could do anything. We could go anywhere.
We had three choices: We could try to work remotely or get something locally in this small town where it’s harder than ever to find remote work; we could get a job in DC, New York, Austin, or go back to Silicon Valley and probably go back to renting and commuting; or blow it up again and go back to Japan. So that’s what we decided to do.
I got my visa that I applied for, so I can be here for the next five years, but it’s going to take a little time to transition.
I’ve got a family of four and a house, so my first step is I’m here in Japan for a month getting together the apartment and all the paperwork for schools and stuff, and then going back and spending a couple of months to finish up prepping my family in the house back in the States.
When I started the company, I knew that I wanted to move to Japan to retire someday — maybe 10 or 15 years out. I’d learn all the ins and outs of how to do it, coach people through it, and then do it myself. My timeline just got much accelerated.
