KEY TAKEAWAYS

• Why are so many Americans moving to Osaka?

• Are you Up for Work in Japan?

• Is it easy to get visa sponsorship to live overseas?

• Michael Machida [American] has been living in Japan for over 25 years!

• The website is located at: https://TheJEGroup.SavvyJapan-Today.com

Dawn's Journey to Living in Japan

Michael Machida Career Search Consultant Tokyo, Japan

A Cocktail, a Conversation, and a New Life in Japan

For years, Dawn carried this quiet little dream. You know the kind—the one you push to the back of your mind when real life starts piling up with bills, promotions, birthdays, and “maybe next year” excuses. Ever since university, where she spent a semester buried in Japanese history books and trying to master keigo in late-night language labs, she felt this pull toward Japan. Not in a touristy way, either—like she genuinely wanted to live there. Build a life. Speak the language, eat convenience store food at midnight, and maybe—just maybe—belong.

But then reality, as it often does, got in the way.

“I tried everything,” she told me once, smiling, but you could tell that smile came with some scars. “English teaching jobs, internships, even random entry-level stuff I wasn’t even qualified for. I just wanted someone to give me a shot. But it was always like… nope. No visa support, or I’d get ghosted after the second interview.”

By the time she hit her early 30s, she almost gave up. Not in a dramatic, movie-ending kind of way. Just that slow, quiet resignation—like, okay, I guess it wasn’t meant to be. So she booked a spring trip to Tokyo “just for fun.” A solo reset. You know those kinds of trips—the ones where you pack a notebook you won’t write in, promise yourself you’ll stay offline, and end up walking ten miles a day just to feel something new again.

She stayed in this little hotel near Ginza—said it had a tiny balcony and the world’s loudest toilet. But at night, she wandered. No plans, no Google Maps route, just vibes. And on her third night, fate showed up wearing jazz shoes and a cocktail grin.

That Night in Ginza

She told me she wasn’t even supposed to go to that bar. Too tired. But something pulled her in. Jazz music spilling onto the sidewalk. A red neon sign. One open seat at the bar.

And there I was.

Just a guy nursing a whiskey, tapping along to the rhythm on my glass like I always do when the music hits right. I noticed her out of the corner of my eye—alone, like me, but relaxed. Curious. She had the look of someone who wasn’t just sightseeing.

When the band took a break, I leaned over.

“Great set, huh?”

She laughed, and I swear, in that moment, it didn’t feel like small talk.

“Yeah. I didn’t expect to find live jazz here, but it’s perfect. You a fan?”

“Big time,” I said. “Come here to clear my head. What about you? On vacation?”

That’s when she opened up. Just enough to let me in.

“Sort of. I’ve wanted to live in Japan for years, but I never found a way to make it happen. So I came just to breathe the air again, you know?”

I nodded because—yeah, I do know. I’ve heard that same sentence in different accents, in broken Japanese, in long emails and hesitant DMs. So I told her the truth.

“I work with people who want to live and work in Japan.”

Her whole face changed. You could see it—the shift from ‘this is just polite bar talk’ to ‘wait, are you serious?’

When she asked how it works, I didn’t go into the weeds. I just said, “It’s kinda loud here. There’s a quiet sushi place down the block. Want to keep talking?”

She didn’t even blink. “Absolutely.”

Sushi, Sake, and Second Chances

The place we went to is nothing fancy—just one of those narrow counters where the chef knows the regulars and the soy sauce isn’t optional. We sat down, ordered some sake and nigiri, and I laid it out.

We talked about her background—marketing, a bit of copywriting, solid experience. I explained how my team works with companies willing to sponsor foreign professionals—not just English teachers, but people with all kinds of skills. IT, design, customer support, content. I told her what I always tell people:

“It’s not about finding a job. It’s about finding your match—and making sure the company believes you’ll actually show up and grow with them.”

She leaned in, soaking up every word like it was the first time anyone had ever told her this was possible.

“I’m just so tired of not knowing where to start,” she said.

That hit me. Because that’s the wall a lot of people run into. Not a lack of desire, but just… no roadmap. No hand to hold through the messy middle.

So I said, “Well, this is your start. When are you flying back?”

“Next Tuesday.”

“Perfect. Let’s meet again before then. I’ll prep some job listings, help you update your resume, and we’ll see what happens.”

That night, something clicked. Not just for her—but for me too.

A Dream Reignited

Two months later, she messaged me: “Guess who’s back in Tokyo… as an employee this time.”

We met for coffee near her new office. She had this soft, stunned look on her face. She said she still couldn’t believe it was real. But it was—she had landed a job with a small but growing marketing team. Her new coworkers helped her apartment hunt. She passed her first N2 practice test. She was living in Japan—not just visiting, not just dreaming.

“I walk to work now,” she said, “pass cherry blossoms, eat too many konbini egg sandwiches, and speak Japanese every day. It’s not always easy—but it’s exactly where I want to be.”

Why I Do This

Look, I’ve met so many Dawns. People with heart, drive, and zero idea where to start. It’s not about connections or magic or luck. It’s about someone opening the right door—and someone else being brave enough to walk through it.

When people ask me why I still do this—helping folks navigate the move to Japan—I always think of stories like hers.

It’s an honor, really. To be the guy who gets to say, “Yeah, come on in. You can live here. Let’s figure it out.”

So if you’re reading this and you’ve had that same quiet dream?

It’s not too late. Not even close.

And who knows—maybe your Ginza moment is just around the corner.

DID YOU SEE THIS? Japanese Convenience Stores Are Amazing!