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The co-owner of Tokyo Confidential Bar shares the challenges of working in Japan

I moved to Thailand to teach English the day after I turned 24. I immediately realized that I was not built for my native London and wanted to create a life for myself outside of the UK.

My next home was in Seoul for two years, followed by a decade in Hong Kong – the only place I’ve ever truly felt at home. There I resumed my career and left teaching, because it had not been part of my career plan, but only a means to lead a life abroad.

I landed my dream job as food and drink editor at Time Out Hong Kong and fell in love with the cocktail scene in Asia. The bartending community in Hong Kong felt like my people – I finally found a place where I really fit in.

I turned my attention to the books and the bartender

I’ve worked off and on in hospitality since I was 14 holding plates in a greasy spoon in London and decided it was time to go back to bartending.

Later, I became the managing editor of DRiNK Asia while bartending at The Old Man Hong Kong. I traveled with the team to do pop-ups and further entrenched myself in the Asian cocktail world. The Old Man went on to rank #1 in Asia’s 50 Best Bars 2019 and my eyes were wide open to this fascinating world.

I eventually left the bar to focus on writing and went on to publish my first book, Cocktails of Asia. It was my love letter to the bar scene that had made me feel so at home. The book caught the attention of my business partner and he recently flew me to Japan to help open a bar, Tokyo Confidential, in the capital. My partner is private and prefers not to be named.

My husband and I were both hesitant to move to Japan

It was a difficult decision to make. One of my toughest so far. We had built a nice house in Hong Kong and formed a tight-knit community of friends. I knew it wouldn’t be the same anywhere else, especially somewhere as geographically large as Tokyo.

But I had to ask myself, what was I really doing? I hit a bit of a ceiling in my editorial role, and my husband—who is a co-founder of Tokyo Confidential—was miserable at his job.

My parents always said how brave I was for moving abroad. I never understood that, because they never traveled much, so how would they know? Courage didn’t even occur to me, but they were right. You are braver when you are younger. In our mid-30s, we were scared of change and knew that if we were going to do it, we were going to give it our absolute all.


Woman standing next to Godzilla statue in Tokyo

The author’s first trip to Japan was in 2012.

Holly Graham



Movement was easier when I was younger

After a dozen trips to Japan over the past decade, I thought I was pretty familiar with the country. Before I moved to Thailand and South Korea, I had never been and I got along just fine. Maybe because my innate ability to adapt anywhere was stronger in my 20s.

It soon became clear that living in Tokyo was a completely different game. Not to mention owning a cocktail bar. And a woman.

Don’t get me wrong – living in Thailand was wild. I was alone in a parking lot for three hours upon arrival with a hot dog and some rice, wondering what the hell I had done. In Seoul, I had to learn the language quickly, otherwise I would have had very limited experience. But like I said, maybe it’s different when you’re younger. Now he felt there was more at stake.

It was stressful moving and starting a new job

Moving to another country and operating a brand new business was even more so. This, combined with the insane amount of red tape carried out through firmly entrenched systems and technology in the 1990s, made moving to Japan difficult.

There is only one bank that non-Japanese can apply for, and things like registering residence and changing address mean waiting in line for hours at the branch office, among other hurdles. Just a few months ago, the government announced that it would no longer use floppy disks, so there’s that.

The language barrier is different when you live here and are not just groping around as a tourist. The pressure to get things done is also different when you have a team of young, enthusiastic bartenders relying on you to guide them.


The bartending team at Tokyo Confidential, a bar in Tokyo, Japan.

Graham and her team at Tokyo Confidential in Japan.

Holly Graham



Living in Japan was not easy

But in a way, that’s the best part. We are here to add something new to the bar scene. There are so many wonderful things about living here that overcome the challenges, and that being said, I live for a challenge.

People are really supportive of me trying to learn Japanese and I know very well how hard it can be to live here. The local and global reception at Tokyo Confidential, our craft cocktail bar, has also been amazing, especially after so many people told me it wouldn’t work.

I see people’s faces light up when they come in and experience our drinks and hospitality. Within just a few months of opening, we were ranked 53rd on the Extended List of Asia’s 50 Best Bars 2024 and were recognized as one of the Top 10 Best International Cocktail Bars by Tales of the Cocktail Spirited Awards 2024.

It’s been less than a year since we opened and I’m so grateful to be able to call Japan home.

Do you have a personal essay about culture shock or relocation that you want to share? Contact the publisher: [email protected].

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