By Alvin Tan | Updated 7 Jul 2025
When I joined Kosé, I knew there was a possibility of an internal transfer to Japan. In fact, that opportunity was one of the main reasons I joined the company.
So when the transfer to Tokyo materialised, I wasn’t caught off guard. I did make a short trip beforehand to meet some of the key stakeholders, and to mentally prepare for what was ahead. But otherwise, there wasn’t much of a formal transition plan.
I was fluent in Japanese—though I hadn’t yet passed the JLPT N1, the highest level of proficiency—so about eight months before the move, I decided to take the test again. It took me two or three tries, but I finally passed. Beyond that? I jumped in, feet wet.
Reality Hits (Hard)
Even with years of language study and cultural exposure, my first few months in Tokyo were tough.
For one, the language barrier was really challenging. To give you context, when I first moved to Japan to work, I already had around ten years of experience with the Japanese language and culture, having also just passed the JLPT N1 earlier that year.
Now imagine this: full-on Japanese from morning to evening, and I also had to quickly pick up business jargon, and adjust to the right way of speaking at work. My brain would shut down after lunch, because it was just exhausting operating in Japanese the whole time. This brain fatigue took around 6 months for me to fully adjust to.
But the hardest part wasn’t the language. It was the working hours.
I had heard stories about long hours in Japanese corporate life, but experiencing it was something else. There were nights I stayed in the office until 11pm, even midnight, preparing documents for meetings scheduled at 9am the next day.
My colleagues would print them out, distribute them, and the papers would be tossed straight into the bin right after. It felt like a waste of time, effort—and trees. The inefficiencies were real. So were the drinking parties, the hierarchy-driven culture, and yes, the harassment—of various kinds. It was, frankly, a wake-up call.
But once I made it through what I now call the “boot camp phase,” I started to see the value of what I was learning. I had picked up key skills: how to write a proper Japanese business email, how to present and collaborate in a culturally appropriate way, how to read the room when the room was Japanese. That foundation helped me move on to better roles—and gave me the confidence to work more on my own terms.
Japan is embracing new worktime norms – slowly but surely
Things have changed since then, both for me and, I think, for Japan. Overtime is less of a norm now, at least anecdotally. The drinking culture has weakened. Work-life balance is more widely discussed. My current role is in a foreign-owned firm with Japanese roots, and the difference in culture is clear. I feel valued for my skills and experience—not just for conforming to the system.
Outside of work, life in Japan has grown on me. I’ve taken up skiing, which I definitely couldn’t do in Singapore. I also enjoy the changing of the seasons—each one brings new food, fashion, and routines. Japan is a society that lives by the rhythm of the year, and it’s something I’ve come to appreciate deeply.
Ultimately, I’ve found that the key to enjoying life in Japan is learning how to make it work for you. And to do that, you need to know yourself.
Thinking of working in Japan? Understand your motivations
Working in Japan may seem like a dream to many, especially Singaporeans. If you’re thinking about working in Japan, it’s important to be clear on your motivation.
If money is your main driver, there are more lucrative countries out there. But if you’re genuinely interested in the culture, language, or lifestyle, Japan can be rewarding in other ways.
Beyond internal transfers, there are several other pathways. You could come on a student visa—either to study at a university or language school—and job hunt from there. If you have in-demand skills, a recruiter might be able to place you, though it’s much easier if you’re already in the country. Japanese companies are still relatively absent from platforms like LinkedIn, so local presence matters.
There’s also the business manager visa route, which requires a 5 million yen investment and a viable business plan. Whichever path you take, language matters. JLPT N1 or N2 opens more doors, and even if it’s not required for your role, it can significantly enrich your day-to-day life. It’s not just about work—it’s about being able to connect with people, understand context, and navigate the little things that add up.
What new relocators should know about Japan living
If you’re planning to stay in Japan long term, take the time to understand the tax and financial systems. It’s not the most exciting part of relocation, but it’s important. For instance, you can claim tax deductions for dependents—even those back home—if you manage the paperwork properly.
I’d also recommend looking into furusato nozei, a policy that lets you redirect part of your municipal taxes to rural areas in exchange for gifts. This system was created to help transfer wealth from the cities like Tokyo or Osaka to the smaller towns and rural areas suffering from depopulation and unable to collect enough taxes for local governments to operate effectively.
Apart from the good feeling of having contributed to a region in need of financial aid, the gifts are extremely good value from a practical standpoint. You definitely get more in return than the fee you pay, and you’re not paying additional tax, just transferring a part of it – so I really recommend it.
Investment-wise, learn about NISA and iDeCo and look into tax-advantaged investment accounts. Unlike in Singapore, capital gains are taxed in Japan, so it’s important to be smart about how you grow your savings.
Building your networks and avoiding the foreigner bubble
When I first arrived, I didn’t seek out the Singaporean community. I didn’t want to get stuck in a foreigner bubble. What helped me most was a colleague—a ‘cultural insider’ who was Japanese, with a global background —who introduced me to his social circle. That one connection snowballed into a wider network, and served as a kind of cultural crash course.
You can go to networking events and other meetups, but I feel like the connection there is quite fleeting and you’re not able to really make friends. Conversely, if you are able to connect well with someone at work, chances are, you will be able to connect with their friends as well. Like attracts like, and this holds true.
Finding Singaporean community in Japan
When I first moved to Japan, I did not actively seek out the Singaporean community, as I wanted to avoid getting trapped within a “foreigner bubble.” Recently though, I’ve reached the stage in my career and life that I’m actively trying to reconnect with my roots.
Only more recently have I started reconnecting with Singaporeans in Japan, and it’s been surprisingly affirming. The community here is diverse: entrepreneurs, corporate employees, expats on assignment, long-term residents. Some are fluent in Japanese, some aren’t. Some are fully integrated, others prefer a bit of distance.
The variety has been striking. It runs counter to the old stereotype that Singapore’s education system produces uniformity. What I’ve found instead is that Singaporeans in Japan each carve out their own path. There’s no single “Singaporean in Japan” story—and I think that speaks volumes.
