In the summer of 1998, with my one-way ticket to Japan, I stepped off a plane at Narita Airport with a backpack, a laptop, and about $2,000 in my pocket.
I had one job offer, a few years of IT work while attending college under my belt, and exactly one semester of Japanese language study. No real fluency. No roadmap.
What I had — maybe the only thing I had — was a strong hunch that this leap could change everything.
🌉 From California to Tokyo: The Why
At the time, I was working in basic Sales and IT support roles in California — configuring printers, installing email clients, selling CRT monitors (before LCD), building custom PCs, setting up a small company, and helping friends and families recover accidentally deleted files. It wasn’t glamorous, but it taught me how to solve real-world problems and explain tech in simple terms — a skill that would serve me long after I left the help desk.
Still, I knew I didn’t want to stay in one place forever.
Japan had always fascinated me. I had a cousin who lived there, and six months before the move, I visited for the first time. I spent a week in Tokyo, and we took a side trip to Hakone, where I experienced Japan’s world-famous onsen hot springs. I didn’t speak the language, but something about the order, rhythm, and quiet respect in daily life made sense to me.
That week planted a seed. When I got back to California, the decision came quickly: I was going to move.
🏠 Living Near Shinjuku with My Cousin
Luckily, my cousin — who had lived in Japan for some time — was supportive. We decided to share a tiny apartment near Shinjuku, Akebonobashi to be exact. I worked days. He worked nights as a floor manager at a local bar in Akasaka, so our paths didn’t often cross during the day.
Still, it was comforting knowing someone I trusted was just down the hall — especially in those early weeks when I was trying to figure out how to pay bills, open a bank account (initially foreigners are only allowed to open a savings account at Japan Post) where to buy groceries, or even how to register at the ward office.
Looking back, those cramped mornings, coffee runs, and mismatched schedules were foundational. That apartment — probably no bigger than a modern hotel room — became my launchpad into the world.
💼 My First Job in Japan
Before arriving, I had secured a job offer from a foreign-owned IT company in Tokyo. It wasn’t a traditional Japanese firm — more of a fast-paced startup run by an international founder who appreciated people willing to dive in.
It was 1998 — the height of the dot-com boom — and Japan Inc. was on a hiring spree. Anyone with basic tech experience, some English, and even the slightest exposure to Japanese could find an opening.
So I said yes. Even though I barely understood the work culture. Even though I couldn’t yet read most signs. Even though I sometimes got lost between train lines.
What I had was just enough ability to figure things out. And I knew how to work hard, adapt, and stay curious.
🚀 Building a Life from Scratch
That first role turned into something more.
I worked hard, asked questions, watched carefully, and took notes after meetings to look up the words I didn’t know. I learned the subtle rhythms of Japanese communication — when to speak up, when to bow, and when to keep listening. After few years, I self-taught myself to a level where I could pass the Level 2 of Japanese proficiently, named JPT Level 2, and passed JPT Level 1 respectively couple of years later to be at par with the Japanese people.
I made mistakes, too. Misread cues. Missed train stops. Got lost in translation — often literally. But I kept showing up.
Over time, that persistence paid off.
I transitioned into larger companies, started managing regional teams, and eventually became a technology executive supporting financial institutions across Asia. But none of that would’ve happened without those first uncertain months — sharing a hallway with my cousin, figuring things out one day at a time.
🍜 Adjusting to Everyday Life
Those first few weeks weren’t glamorous. Most mornings, I’d wake up to the faint hum of the trains heading toward Shinjuku, pour myself an instant coffee, and step out into the city’s buzz — with a paper map folded in my pocket and a head full of questions.
Simple things became mini-adventures:
- Figuring out how to pay my utility bills at the convenience store
- Memorizing how to say “I’d like to open a bank account” in keigo-level Japanese
- Standing in line at the supermarket unsure whether to bow or nod or just smile awkwardly at the cashier
I didn’t have a smartphone or Google Translate. Just instinct and the occasional kindness of strangers — usually delivered with slow Japanese and a lot of pointing.
In hindsight, those everyday struggles taught me patience, humility, and a deep respect for the routines behind Japan’s orderliness.
👥 Learning Culture Through Observation
In the office, things moved at a different pace than in the U.S. Decisions were slower, meetings more formal. Although it was run by an Australian entrepreneur, it had all the characteristics a Japanese company would have. There was hierarchy, even in silence.
But what impressed me most wasn’t the structure — it was the unspoken understanding among colleagues. I began to learn when a pause meant “think deeper,” or when a sigh meant “not now.” I learned how to read between the lines, and how trust was built slowly, through consistency, not charm.
Every email I sent took twice as long to write. Every presentation was double-checked, out of fear of accidentally crossing a cultural line I hadn’t learned yet.
And yet, with each passing month, it got easier. A teammate would start greeting me more warmly. A boss would ask my opinion more directly. One day, a client said, “Your Japanese has improved.” It wasn’t fluent — but it was enough to show that I cared. That I belonged.
My very first job was a placement role at one of the largest US banks that had a branch near Shinagawa, called Tennozu Isle. To get there, you need to get off at a major station called Hamamatsu-cho (part of the Yamanote line, a green circle line in Tokyo). My first role was to deploy a new email client to all 2,000+ PCs in the entire building. The job required me to visit users’ desk face to face and run install scripts as fast as I can. I did my job so fast that an IT company that owned the actual project wanted to hire me on the spot. Well, I kept my gentlemen’s promise with the company then (stay there for at least 2 years and move on).
🌆 Weekends in a New World
Weekends were my chance to breathe.
Sometimes, I’d wander aimlessly through neighborhoods like Nakano, Kichijoji, or Shimokitazawa, soaking in the alleyway cafés and tiny bookstores. Other days, I’d hop on a local train and get off at a random station, just to see what the neighborhood felt like.
Tokyo was (and still is) a city of contradictions: ancient temples tucked behind neon-lit arcades, quiet parks just blocks away from chaotic intersections. I loved that. I still do.
Though I was far from home, the unfamiliarity didn’t feel isolating — it felt alive. Like the city itself was inviting me to rewrite what “home” meant.
🔄 My Cousin and the Night Shift Life
Back in our apartment, my cousin and I lived almost separate lives — ships passing between dusk and dawn. He’d leave for his bar shift as I was brushing my teeth. I’d come home just as he was about to sleep.
But in those rare overlap hours — weekends or early mornings — we’d catch up over convenience store coffee, local drinking place called Izakaya (our favorite spot was Shirakiya, a chain store all over in Japan selling cheap food and sake) and swap stories about life in Tokyo. His world was nightlife and crowds. Mine was business suits and morning commutes. But somehow, those brief talks grounded me. I wasn’t alone.
Without him, I don’t think I would’ve adjusted as quickly. There’s something about sharing the struggle with family, even if you’re on different schedules and living out different dreams.
📈 Seeds Planted for the Future
That first year taught me more than any job or classroom could. It shaped how I lead teams today. It shaped how I raise my kids — to stay curious, to observe before judging, to embrace discomfort as growth.
Sometimes people ask me, “Wasn’t it scary to move to Japan with so little?”
Yes, it was.
But fear wasn’t the loudest voice in my head. Curiosity was. So was a quiet belief that if I kept showing up, something good would happen.
And it did — over and over again.
✍️ What This Taught Me
Looking back now — two decades, three kids (one more arriving in August 2025), and countless moves from one apartment to another — I’ve realized something:
The scariest moves are often the ones that lead to your best chapters.
I didn’t have perfect Japanese. I didn’t have a clear 5-year plan nor 10-year plan. I had a one-way ticket, a cousin to split rent with, and the willingness to learn from whatever came next.
And that was enough.
📬 Coming soon on Life in JP:
- Lessons from working in Japan’s IT sector as a foreigner
- Culture shock moments — and how I adapted
- How I raised a bilingual family in Tokyo
- Mistakes I made (and what I’d tell my younger self today)
If you’re considering your own leap — into Japan, a new career, or a new version of yourself — I hope this helps you believe in what’s possible.