Why I Left Singapore & Moved to Japan

Dear Diary,

As I sit here in Tokyo, it’s hard to believe how much has changed in such a short time. Not too long ago, I was with the morning rush crowds of Singapore’s Downtown Line, heading to my job at post-Elon era Twitter, feeling secure yet unsure about what the future held. Fast forward to now, and I’m in a completely different world, balancing Japanese language classes, remote work, and exploring one of the most dynamic cities in the world.

Busy streets of Shinjuku Kabukicho.

In this post, I want to take a step back and reflect on why I made the decision to leave Singapore and move to Japan. I’ll walk you through my thought process: how I went from working in a stable corporate role to taking a leap into the unknown by quitting my job and moving to a country with a language I barely speak (Duolingo was a hard carry). I’ll also explain why Japan was the right choice for me over other countries, the challenges I faced in the transition, and how I’m adapting to my new life here.

So if you're curious about what made me take this big step, keep reading. This is my journey so far.

Life before Japan

The amazing team i was leaving behind

Before Japan, life was all about routine and stability. I was working at Twitter in Singapore, which, I’ll admit, was an exciting gig at first. My job was centered around global stakeholders, managing projects, and learning the ropes of the advertising world. The people I worked with? Absolutely fantastic. It really felt like a community, which made it all the harder to leave.

In terms of working hours, I did have to juggle different time zones, but I found it rewarding to learn from other markets. With the energy of a fast-paced global workplace, I always had my sights set on eventually taking up an overseas appointment. 

In fact, I accepted the job because of its potential for relocation. But when the Elon Musk takeover happened, the environment shifted. The company no longer felt like the place I had signed up for. The projects changed, and I wasn’t growing in the way I had envisioned.

Outside of work, though, life was good. My family was doing well, and I had strong connections with my friends. But I had always dreamed of living and studying abroad, something I never had the chance to do during university. 

At 26, I realized that if I didn’t make a change soon, I might just settle into the familiar, and that idea didn’t sit well with me. That’s when the thought of moving to Japan started to take hold. I knew I needed to push myself out of my comfort zone. Otherwise, I’d stay in the same place, both physically and mentally.

What made me want to f*ck all and leave Singapore?

Honestly, the thought of leaving Singapore had been simmering for a while. I loved my job at Twitter at first, and working with global markets was exciting, but as time went on, especially with the Elon Musk takeover, things changed. The projects weren’t the same, the environment shifted, and I felt like I wasn’t growing in the direction I wanted to. And let’s face it, when you’re stuck in a rut, sometimes you just want to shake things up.

Leading up to the decision, my mind was constantly going back and forth. On one hand, I had this stable job, a great team, and a life I was familiar with. On the other hand, I kept feeling like I was missing out on something more. I had always wanted to experience life abroad, and the idea of immersing myself in a different culture felt like the challenge I needed. 

At the same time, I was 26, and there was that quiet voice telling me, "If not now, when?" So the thought process was a mix of practical considerations (like visas, finances, and language) and a deeper need for personal growth and change.

In the months leading up to the decision, I felt restless. I was going through the motions of daily life: work, socializing, family. But underneath it all, I knew I wasn’t completely satisfied. It’s like I could feel the itch to try something new, growing stronger each day. 

The changes at work weren’t helping either, and while I was still grateful for my role, it felt like the timing was right to look beyond it. I wouldn’t say I was unhappy, but I definitely wasn’t fulfilled.

Farewell card and gift from my ex-colleagues.

I remembered the exact moment when you decided to leave clearly. I was sitting in the office one afternoon, going through the motions of a project that I just couldn’t connect with. I looked around and thought, "Is this what I want to be doing in five years?" 

That’s when it hit me. 

If I stayed, I’d be stuck in this same cycle. It wasn’t an impulsive decision, but that moment was like a switch flipping. I realized I needed to take control of my path, and leaving was the only way to do that.

When I finally made the decision, it was like a weight lifted off my shoulders. Don’t get me wrong, I was nervous. Quitting a stable job in Singapore to study abroad in Japan isn’t exactly a small step—but there was also a sense of excitement and relief. It felt empowering to know I was doing something for myself, something that aligned with my goals and dreams. The future was still uncertain, but for the first time in a long time, I felt like I was moving forward in a meaningful way.

Till today, friends are very supportive. When they come to Japan, they’d bring me a taste of Singapore!

Reactions were pretty mixed! My family was supportive, but there were definitely concerns about me leaving a stable job and heading into the unknown. They knew I had thought it through, but like any family, they wanted to make sure I wasn’t making a reckless decision. 

My friends were more excited for me. They saw it as this bold, adventurous step and were cheering me on. As for my colleagues, it was bittersweet. They were happy for me but sad to see me go. A lot of them understood the need for change, especially given the shifts at the company, but there were definitely some "Are you sure?" moments too.

Why did I choose to move to Japan?

Japan has always been on my radar, especially because of my time at Twitter. Twitter is huge in Japan, and through my role, I was constantly exposed to their advertising landscape, which I found absolutely fascinating. 

The way brands communicate here is so different from what I was used to in Southeast Asia, and I couldn’t help but want to dive deeper into it. The idea of working in Japan’s advertising industry was a big motivator. There’s so much creativity and energy in how they connect with audiences, and I knew it would be an amazing challenge.

I moved to Tokyo, and honestly, it felt like a natural choice. Tokyo is a major advertising hub, so it aligned perfectly with my career goals. Plus, in terms of living conditions, it’s quite similar to Singapore. The public transport system is efficient, things are accessible, and the overall pace of life was something I could adapt to easily. 

Apart from the language, of course! It wasn’t just about logistics though; I had ex-colleagues in Tokyo who were incredibly supportive, and a childhood friend who could help me settle in. Having that kind of community around made the move much less daunting.

Not an easy journey where I write essays every week and have my friends proofread for me.

My main goal was to become proficient in Japanese. While I had learned some basics, I knew that if I wanted to work in the advertising industry here, I needed to master the language. 

Beyond that, I wanted to gain firsthand experience of living abroad, something I hadn’t done during university. The dream is to eventually combine my passion for advertising with my new language skills and work within Japan’s advertising sector. It’s about pushing myself out of my comfort zone and growing both personally and professionally.

What is life like in Japan?

My first autumn experience @ Showa Kinen Park (昭和記念公園) with my Tokyo ex-colleagues

Living in Japan has been quite the adventure so far, and it’s different in many ways but also similar enough to Singapore to make the transition easier. The transportation is super efficient, and everything is so accessible. 

But what really adds excitement here are the four seasons and the variety of domestic trips you can take. I’ve already managed a few short trips to places like Karuizawa, Yamanakako and other popular local destinations, and it’s been such a refreshing change compared to Singapore's year-round tropical weather.

I'm currently living in a sharehouse with mostly Japanese housemates, and it’s been a pretty interesting experience. Everyone here seems to live by the "work hard, play hard" mantra. They’re out the door around 7 a.m. for work and back by 8 p.m., but come weekends, they’re up early and off to enjoy their time. 

As for me, my first three months were intense with school, catching up on my studies while also juggling the endless paperwork that comes with moving to Japan. Thank goodness for my ex-colleague, who really helped me navigate all that!

A glimpse into Japanese culture

One of the icebreakers I do when out with friends is to take ‘purikura’ or ‘neoprint (in Singapore)’

Japanese people, in general, seem to lean towards being more introverted, especially when it comes to starting conversations. It’s not that they’re unfriendly, but there’s a certain reserved nature to social interactions here. 

Most people tend to keep to themselves, and I’ve noticed that they’re not likely to strike up a conversation unless necessary. However, when I make the effort to speak—even with my broken Japanese—they’re very polite and responsive. They might not chat your ear off, but they do engage when approached, and there’s always a sense of respect in how they communicate.

It’s been a learning curve, figuring out when and how to approach people, but I’ve found that once you do break the ice, they’re kind and considerate. The politeness in their behaviour really stands out, and while conversations might be brief or formal, you always feel a sense of warmth in their responses.

The food is, without a doubt, delicious and varied. But, coming from Singapore where we’ve had this whole campaign to reduce our salt intake, I find Japanese food a bit on the salty side. I actually cook a lot at home because of that. 

It’s funny, even my friends from Singapore who visit have noticed the same thing! That being said, eating out here is relatively affordable, especially at gyudon-ya-san (which means beef bowl shops), but if you factor in Japan’s salary levels, it can feel pricey at times.

One type of soup curry that is packed with vegetables and turmeric rice!

One dish that has become a personal favourite of mine is soup curry, a speciality from Sapporo, Hokkaido. I had never heard of it until I moved here, and now I have it at least three times a month! It’s loaded with vegetables and tender chicken, served with turmeric rice. What’s amazing is that every shop makes it a little differently with their own spice mix, so I never get bored of it.

Oh, definitely. One that stood out to me was how much Japanese people love their bathtub soaking time! It’s serious business here. Even on weekdays, they’ll spend a full hour soaking in the bath. Living in a sharehouse, I noticed that the bathtub room is always booked solid, whereas the shower is hardly used. 

As a Singaporean, I found it a little surprising because we tend to favour efficiency, especially when it comes to things like showering. We’re all about getting in and out quickly, but here, the bath is almost sacred.

Another thing I didn’t expect was Japan’s strong phone call culture. Whether it’s making a reservation at a restaurant or asking questions, it’s almost always done by phone. Since tourism picked up again post-COVID, locals have had to reserve tables in advance, sometimes up to two days before, especially in places like Tokyo that are swarming with tourists. 

And interestingly, things like movie tickets have a flat fee. No matter the day or time, it’s always 2,000 yen. Just little things like that make life here a bit different from what I’m used to, but all part of the charm of living in Japan!

Travelling in Japan

My trip to lavender field and flower fields at Furano, Hokkaido in July 2024

Since moving here, I’ve had the chance to explore quite a bit, and I have to say, Japan is incredibly diverse when it comes to travel experiences. I’ve visited Hokkaido for its lavender fields, Karuizawa for the mountain views, Okinawa for the beaches, and places like Kawagoe, Kamakura, and Enoshima for more local vibes. 

Each place has its own charm, and what I love most is how easy it is to get around thanks to Japan’s efficient train lines and express trains. There’s something special about hopping on a train and arriving at a new destination in just an hour or two. 

The scenery here is also a big change from Singapore. Whether it’s mountains, beaches, or just strolling through nature, there’s so much to see. And let’s not forget the food! Every region has its specialties, from Hokkaido’s seafood to Okinawa’s unique dishes, things I never really experienced back home.

What am I currently busy with?

Studying at a cafe and revising for school.

Lately, I’ve been juggling quite a bit! My weekdays are pretty structured. I start with my remote work for a Singapore-based company, which helps me manage my finances while I’m in school. After that, I head off to my afternoon language classes, followed by a bit more work once classes are done. Evenings are my downtime. Sometimes I’ll head to the supermarket to cook, and on other days, I’ll meet up with friends for dinner. It’s nice to balance out the week this way.

Weekends are my time to unwind and explore. I often travel outside of Tokyo, or I’ll stick around the city and check out thrift shops in places like Kichijoji or Koenji. There’s always something new to discover.

Friend shopping at a thrift shop at Kichijoji.

In addition to all that, I’ve been actively interviewing for advertising roles here in Japan. My goal is to land a job and gain hands-on experience, as I believe I learn best by jumping right into real-world challenges, rather than just staying in the classroom.

In the short term, I’m laser-focused on getting my N2 language certification this December. Language proficiency is key to finding work here, and while I can understand a lot, I’m still working on speaking smoothly and confidently. To help with that, I’ve started doing 15-minute oral practice sessions every morning with a language buddy in Hiroshima who helps correct my speech.

Long-term, I’m aiming to pass the N1 exam by next July, as that will significantly boost my chances of employment. I’ve renewed my student visa and am studying for another year to improve my language skills. 

Balancing everything has been a challenge, but I’m still trying to figure out how to optimise my schedule. There’s always that feeling that I could be doing more; whether it’s spending more time on language studies or finding new ways to practise speaking. 

But for now, I’m taking it one step at a time, making sure I stay consistent with my daily habits and focus on the bigger picture and the eventual goal of working in the advertising industry here in Tokyo.

Do I regret leaving Singapore to move to Japan?

I don’t regret leaving Singapore to move to Japan. Not at all.  

Sure, there have been challenging moments. Especially when I first arrived and had to adjust to the language barrier and tackle the paperwork. But overall, this move has been incredibly rewarding. 

I’ve always wanted to push myself out of my comfort zone, and Japan has given me just that. While I do miss the familiarity of Singapore, especially family and friends, this adventure has been worth it. The new experiences, the growth, and the discovery have made it clear I made the right decision.

Park near my sharehouse, which has only local Japanese enjoying the cherry blossoms while picnicking.

Would I recommend anyone leaving Singapore?

Yes, but with a few considerations. 

If you’re thinking about leaving, make sure you weigh your options carefully, especially financially. In my case, I don’t have a partner, house, or other significant obligations, so I’m in a good position where I’m only responsible for myself. It’s definitely easier to make the move before family commitments grow, like parents getting older. 

I also read on the Reddit thread, that many Singaporeans are much happier with their work-life balance abroad despite taking a pay cut. So if money is a big factor for you, it might be a tough decision. But if you value experiences over income, or if you can afford the shift, I would say it’s worth taking the leap.

Picture of my family on my desk as I do work to remind me of them.

What’s next for me?

Well, I’m still focusing on improving my Japanese and soaking in as much of Japan as I can. There’s so much left to explore, places I haven’t visited yet, food I haven’t tasted, and experiences that are just waiting for me around the corner. I’m eager to visit more spots outside Tokyo, whether it’s another beach in Okinawa or a quiet mountain town.

Professionally, my goal is still clear: to transition into the advertising industry once my language skills are up to par. I’ve been pushing myself with interviews, studying, and finding ways to practise my Japanese every day. It’s been a process, but I’m learning so much along the way.

For now, I’m just enjoying the journey, taking it one step at a time. There’s no rush! With plenty of trips, meals, and learning experiences ahead, I know I’m right where I need to be. And who knows? Maybe in my next entry, I’ll be writing about landing that dream job. 

Until then, here’s to the next adventure.