The Island of Dreams: Why I Bet on Okinawa’s Entrepreneurial Future

There’s a peculiar kind of loneliness that comes with being ahead of your time. Not the trendy kind where you’re the first person in your neighborhood with a smartphone and everyone thinks you’re either visionary or pretentious (spoiler: they usually think both). No, I’m talking about the kind where you’re standing in a classroom in Okinawa in 2010, talking about social entrepreneurship and startup culture, and your students are looking at you like you just suggested they open a lemonade stand on Mars.

But let me back up.

The Happiness Hypothesis

I’ve always believed that the pursuit of happiness isn’t just some throwaway line from the American Declaration of Independence—it’s the fundamental engine of human progress. And here’s the thing about happiness that took me years to understand: it’s not just about personal contentment. True happiness, the kind that sustains you through 3 AM pivots and rejected pitch decks, comes from creating something meaningful that serves others.

This is why I fell in love with the idea of transforming Okinawa into a “Startup Island.”

Okinawa, with its crystal blue waters and laid-back island rhythm, might seem like an unlikely place to launch a startup revolution. Why would anyone want to disrupt paradise? But that’s exactly the point. What if entrepreneurship wasn’t about grinding yourself into dust in some soulless tech hub? What if it could be about building businesses that enhance life, preserve culture, and create genuine well-being?

A Prophet Without Honor (Or Maybe Just Without Wi-Fi)

Around 2010, I started introducing practical entrepreneurship programs into university courses in Okinawa. I wasn’t just teaching theory from dusty textbooks—I was encouraging students to actually start businesses, to think like social entrepreneurs, to see problems as opportunities wrapped in very convincing disguises.

The timing, as it turned out, was spectacularly terrible. Or spectacularly good, depending on how you look at it.

In most developed countries, entrepreneurship education was already well-established. But in Japan, and especially in Okinawa, suggesting that students should consider starting their own businesses was like suggesting they should take up extreme ironing. Sure, it’s technically possible, but… why?

I was too early. Way too early. Like showing up to a party at 6 PM when it doesn’t start until 10 PM levels of early.

The Long Wait

Japan’s “Lost Two Decades” had created a generation of young people who were, understandably, more focused on landing secure jobs than launching risky ventures. The government’s response? Career education—which in practice often meant “here’s how to write a better resume” rather than “here’s how to create your own opportunities.”

Meanwhile, the Ministry of Economy, Trade and Industry was pushing entrepreneurship, while the Ministry of Education, Culture, Sports, Science and Technology was pushing career guidance. It was like watching two people try to dance together when they’re listening to different songs. Awkward doesn’t begin to describe it.

I kept teaching. I kept believing. I kept imagining a future where Okinawa wasn’t just a beautiful place to visit, but a vibrant ecosystem where people came to build their dreams. Where the pursuit of happiness meant creating businesses that solved real problems while respecting the island’s unique culture and natural beauty.

The Long-Awaited Dawn

Then, in 2022—just as I was preparing to retire from university life—the Japanese government declared it the “First Year of Startup Creation.” They launched a five-year plan to promote entrepreneurship education not just in universities, but in elementary, middle, and high schools.

The timing would be hilarious if it weren’t so bittersweet. Imagine training for a marathon for twelve years, and then the day after you retire, everyone decides marathons are cool and starts running them.

Part of me felt frustrated. “If only this had come sooner,” I thought. “How many more students could I have reached? How many more entrepreneurs could I have helped create?”

But here’s where that pursuit of happiness comes back in. Because entrepreneurship—real entrepreneurship—isn’t about personal glory or perfect timing. It’s about planting seeds, even if you won’t be around to see the full harvest.

The Source of Knowledge, The Wellspring of Hope

In the materials I wrote during those early days, I talked about “知の源泉”—the wellspring of knowledge. I believed then, and I believe even more strongly now, that Okinawa has something special to offer the world of entrepreneurship.

It’s not just about tax incentives or co-working spaces (though those help). It’s about a different philosophy of business—one where success isn’t measured purely in unicorn valuations and exit strategies, but in sustainable growth, community impact, and yes, happiness.

Okinawa has a concept called “yuimaru”—the spirit of mutual assistance and cooperation. What if that became the foundation of a new kind of startup culture? One where competition doesn’t mean crushing your rivals, but elevating everyone together?

What I Expect from Okinawa’s Future

When I close my eyes and imagine Okinawa’s entrepreneurial future, I don’t see a copy of Silicon Valley transplanted onto a tropical island. (Please, no. We have enough tech bros ruining paradise.)

Instead, I see:

Young entrepreneurs who’ve grown up with entrepreneurship education from elementary school, building on the foundation laid by pioneering programs like Ryukyu Frogs—a visionary initiative that began 17 years ago, sending Okinawan youth to Silicon Valley to cultivate entrepreneurial mindsets. What started as an Okinawan experiment has now spread beyond the prefecture, proving that the island was quietly incubating innovation long before it became national policy.

These young people view starting a business not as a rebellious act but as a natural extension of solving problems they care about. They’re building companies that address real issues—aging populations, environmental sustainability, cultural preservation—while maintaining work-life balance that doesn’t require quotation marks and a weary laugh.

Social enterprises that prove you can do well by doing good, combining Okinawa’s traditional values with innovative business models. They’re exporting not just products but a philosophy: that business can be a force for human flourishing.

A bridge between nations—what Okinawa historically called “bankoku shinryō”, meaning a bridge connecting all countries. Entrepreneurs from around the world come not to “disrupt” but to learn a different way of building, exchanging ideas and wisdom across cultures. Where success is measured not just in growth metrics but in well-being indicators. Where the pursuit of happiness isn’t a naive dream but a strategic advantage, and where Okinawa’s ancient role as a crossroads of cultures becomes its modern identity as a crossroads of innovation.

The Beautiful Irony

Here’s what makes me smile: I was too early, yes. But being too early meant I got to plant seeds in virgin soil. The students I taught in those “too early” years? They’re out there now, and some of them have gone on to start their own ventures, to think differently about their careers, to question the conventional path.

The government’s new policies will water those seeds. The next generation will see an even fuller bloom. And the generation after that? They might just transform Okinawa into the Startup Island I once dreamed about.

Innovation, as it turns out, has always been about recognizing its importance—even when you’re unfashionably early to the party. Even when you’re standing alone in a classroom, talking about possibilities that seem impossible.

The Pursuit Continues

As I watch the new wave of entrepreneurship education roll out across Japan, I feel something unexpected: not regret for being too early, but gratitude for having been early at all.

Because here’s the secret about the pursuit of happiness: it’s not about the destination. It’s not about being there when your vision finally becomes reality. It’s about the joy of believing in something bigger than yourself, of working toward a future you might not fully see, of trusting that the seeds you plant will grow.

There's an old Greek proverb that captures this perfectly: "A society grows great when old men plant trees in whose shade they shall never sit."

I expect great things from Okinawa’s future. Not because the policies are finally in place, but because the dream was always worth pursuing. Not because entrepreneurship education is now mainstream, but because the students—past, present, and future—deserve the chance to create lives of meaning and purpose.

And if they can do that while enjoying some of the world’s best beaches? Well, that’s just good business sense.

The island of dreams is becoming an island of dreamers who do. And that, my friends, is a future worth betting on—even if you were awkwardly, wonderfully, stubbornly too early to the party.

I may never sit in the shade of the trees I planted. But sometimes, on quiet mornings, I imagine I can hear the rustle of leaves beginning to grow. I picture students I'll never meet, standing beneath those branches, launching ventures I'll never see, solving problems we haven't even discovered yet. They won't know my name. They won't know about those lonely classrooms in 2010, or the programs that seemed too ambitious, too soon.

And that's exactly how it should be.

Because the most profound act of happiness isn't achieving your own dreams—it's creating the conditions for others to achieve theirs. It's believing in a future you'll only glimpse, not inhabit. It's planting seeds with trembling hands, knowing you may never taste the fruit.

After all, someone has to set up the speakers and get the music playing.

And if that music becomes a celebration of happiness itself—if it helps even one young person in Okinawa believe they can build something meaningful, something that matters, something that makes the world a little bit better—then those twelve years of being "too early" weren't too early at all.

They were right on time.

For the future.

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Note: Here’s where you’ll find the research notes connected to this article (coming soon)