Key Points
Moving to Japan wasn’t a sudden whim for Nick Woolsey. It was the outcome of months of doing the math, watching costs climb, and feeling a steady erosion of stability in the US—despite years of higher pay.
Woolsey, 39, says the combination of sky-high housing, expensive childcare, and a job market marked by recurring layoffs pushed his family to make a decision that once felt far off: leave the US and return to Japan.
In an as-told-to account based on conversations with Woolsey, he describes how his family went from earning Silicon Valley-level incomes to feeling like they were “basically just getting by,” and why he now believes their best path forward is starting over abroad.
Moving to Japan After Job Instability and Rising Costs
Woolsey had already lived in Japan for years before returning to the US. This time, he says, he’s going back with a clearer plan—and a different stage of life in mind.
After spending the last six years in the US, Woolsey says he has decided on moving to Japan on a “highly skilled professional visa.” He describes the visa as giving him the ability to be in Japan for the next five years, though he also notes the transition will take time.
His immediate plan is practical and staged. Woolsey says he is currently in Japan for a month to line up essentials—setting up an apartment and handling paperwork connected to schools and other logistics. After that, he expects to return to the US for a couple of months to finish preparing his family and deal with the realities of leaving behind a house and an established life.
It’s not just a relocation. It’s an attempt to regain control.
Woolsey says that even while earning more than he ever had before, the financial pressure in the US kept building. In Silicon Valley, he estimates his family’s rent was about $5,000 a month, while preschool cost around $3,000 a month.
That’s roughly $8,000 each month tied up in just housing and preschool.
And even when they made changes to reduce costs—leaving Silicon Valley and moving to a smaller town in southern Washington—Woolsey says expenses continued creeping up.
At the same time, the sense of job security didn’t improve.
Woolsey says his company seemed to be going through layoffs every six months, and he felt it was only a matter of time before his position was cut. Eventually, he says, he got the notice: his job was going away.
Not long after, Woolsey says his wife and her company “came to an agreement” that their time together was also finished. The family went from two incomes to relying on a startup Woolsey had been building.
That’s when the decision became less theoretical.
Woolsey says that with the “golden handcuffs” off, the family looked at their options: try to find remote work or local work in a small town where remote jobs felt harder to land, move to a major US job hub like DC, New York, Austin, or back to Silicon Valley, or commit to moving to Japan.
They chose Japan.
From Exchange Programs to Tokyo: How Japan Became Familiar
For Woolsey, moving to Japan is also a return to a place he’s known since his teens.
He says his earliest experience came through a short one-week high school exchange program linked to sister cities—relationships designed to support student exchanges between US communities and corresponding locations in Japan.
Later, as a college student in Oregon, Woolsey says he joined a six-month exchange program through a sister school relationship with Tokyo International University. After that program ended, he returned to the US.
He went on to earn an MBA. Then, he says he learned about a program in Japan where he would work as a civil servant, helping facilitate exchange between his home country and Japan, supporting nonprofits, and doing translation work.
Woolsey says he applied and was accepted.
But when he arrived in 2011, he says his placement didn’t match what he expected. Instead of nonprofit-focused government management, he says he was told to teach English—work he did for two years.
Over time, his life in Japan deepened beyond work.
Woolsey says he met his wife in Japan. She is also a foreigner, and he describes her as Russian. She was in Japan through a similar type of work exchange program.
As their relationship progressed, Woolsey says his wife got a job in Tokyo and pressed the question of whether he would move. He agreed, though he says timing created a gap: he had just renewed his teaching contract, and she spent nearly a year in Tokyo before he later got a job, moved up, and entered tech work in the city.
For years, Japan was home.
Then parenting changed the equation.
Parenting Stress and the First Move Back to the US
Woolsey says having a child in Japan brought a kind of pressure he wasn’t prepared for—less about culture and more about the intensity of raising a baby without close family nearby.
He describes the early months as overwhelming. He says he didn’t have time off work to adjust, and his wife was home alone, creating what he calls a stressful first three months.
The family did receive help at times, Woolsey says, with his wife’s mom coming from Russia and his own parents visiting from the US when they could. But he describes it as intermittent support, not the steady day-to-day help many parents rely on.
Childcare was another strain.
Woolsey says that because they lived in the city, getting into day care was difficult—and they didn’t get in. Still, he notes what he saw as a major positive: his wife received maternity leave that gave her two years off.
They stayed through that period, but the bigger question lingered: could they raise their child in Japan without nearby family?
Woolsey says the answer became clear: they needed help, and their families weren’t moving to Japan.
So the family decided to return to the US.
They moved back to Woolsey’s hometown, The Dalles, Oregon, in 2019. But the stability they hoped for didn’t last long.
Woolsey says his wife received a job offer from an international startup with a US office, and the company asked her to move to Silicon Valley. The family relocated, and he frames the move as financially logical at the time because US salaries were significantly higher than what they had earned in Japan.
They were earning more.
But Woolsey says they weren’t getting ahead.
The Day-to-Day Costs That Made the US Feel Unsustainable
Woolsey’s critique of life in the US isn’t about a single bill. It’s the compounding feeling that costs don’t stop rising—and that the lifestyle available for the money didn’t match what he believed was possible elsewhere.
He points to how rarely his family went out to eat in recent months due to inflation and everyday price pressure.
In one example, Woolsey describes taking his family of four to food trucks. The order wasn’t extravagant, he says: a couple of beers, a hamburger, and some meat on a stick. One of the children was only one year old and didn’t eat much. The total, he says, came out to $100.
Woolsey contrasts that with what he says he could do in Japan for the same amount, arguing that the “scale” and “quality” feel different there.
He also describes Japan as having wide-ranging food quality across price points. In his view, it isn’t only Japanese cuisine that’s strong, but many international options—though he jokes that Mexican food is the exception.
For Woolsey, those everyday experiences became part of a bigger question: how to keep a Western-style career while improving quality of life.
He says he started thinking: how could he maintain a Western pay level and work-life balance while achieving what he describes as Japan’s lower cost of living and better quality-of-life value?
That line of thinking didn’t stay theoretical for long—because his work situation changed.
Turning a Personal Goal Into a Business
As layoff fears grew, Woolsey says he realized he needed to use other skills to build something of his own.
He started a business that helps people relocate to Japan, effectively teaching others how to handle moving to Japan “on their own terms,” as he puts it—because it was what he wanted for himself.
While he was building the website and working with his first clients, Woolsey says he received notice that his job was ending.
Then his wife’s employment ended, too.
With those changes, the family’s choices narrowed. Woolsey describes three paths: try to find remote or local work while staying in their small town, move back to a major US job center with the likelihood of returning to long commutes and expensive renting, or commit fully to moving to Japan.
They chose the third option.
Woolsey also notes that when he started the business, he originally thought of Japan as a long-term retirement destination—something like 10 to 15 years out. But layoffs, rising costs, and the shift to running a startup accelerated that timeline significantly.
What Happens Next for the Family
Woolsey says the decision for moving to Japan is made, but the execution will be gradual.
He describes a family of four, a house, and the need for a careful transition. His first step is a short stay in Japan focused on setup—apartment arrangements and school-related paperwork—before returning to the US to wrap up preparations over the next couple of months.
His longer-term status in Japan, he says, is supported by the visa he applied for, giving him a five-year window to build the next chapter.
While Woolsey’s account is personal, it lands in a moment many families recognize: when a “good salary” no longer guarantees stability, when childcare becomes a second rent payment, and when layoffs turn career planning into guesswork.
For Woolsey, moving to Japan isn’t framed as an escape. It’s a strategy—one built from lived experience in both countries, shaped by family needs, and accelerated by the math of modern US life.
Conclusion
Woolsey’s story traces a full circle: early exchange programs, years living and working in Japan, a return to the US for family support, and then another pivot when costs and layoffs made stability feel out of reach.
Now, he says, moving to Japan is no longer a distant retirement idea. It’s the plan his family is acting on now—step by step—after rent, preschool bills, and job losses reshaped what “making it” in the US looks like for them.
