In my last article, I wrote about standing on the eve of my son Ziggy’s high school graduation. This chapter is about what came next—a journey that became as much about my own growth as a father as it was about exploring a new country.
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The Challenge
I knew Ziggy was graduating and wanted to do one more big trip together before he headed off to college. When I asked him where he wanted to go, his answer surprised me: “Japan.”
I’ll be honest, I thought it was a crazy idea. “Buddy,” I said, “I don’t think that’s going to happen. It’s really far, it’s a lot.” But I stayed open and I realized that I had some open cityHUNT and non-profit work in Japan. So instead of shutting down his dream, I made him an offer that was equal parts challenge and leap of faith: “You want to go? You plan the trip.”
I honestly wasn’t sure he’d follow through. But Ziggy surprised me. I’d been sharing content from travel writer Kevin Kelly with him—stories about seeing the world with intention and purpose. Using Kelly’s blog and AI as his guide, he came back with a detailed plan for a two-week journey across Japan. My role shifted from trip planner to supporter, and I had to do something that’s never easy for any parent: step back and trust him to lead.
Rediscovering Japan
The last time I was in Japan, I was 21 years old—25 years had passed. I remembered the energy, but this experience felt completely different. Japan is a country built on mindfulness and order, and you feel it in everything from how people treat each other to how they care for their spaces.
You can tell a lot about a culture by its bathrooms, and in Japan, they’re remarkable. We found heated toilet seats and thoughtful automatic features in the most unexpected places—that level of care permeates everything. The spirituality is tangible too, with Shinto shrines and Buddhist temples tucked into neighborhoods and mountainsides, offering these perfect pockets of calm in the middle of busy cities.
There was also a pleasant surprise: despite Japan’s reputation for being expensive, the strong dollar made it one of the most affordable places I’ve traveled recently.
The Defining Moment
Our most memorable day began on Miyajima, a small island just outside Hiroshima. We decided to hike Mount Misen via the traditional path—2,000 stone stairs leading to the summit. Along the way, we’d stop at small shrines to rest and meditate. The climb was challenging but beautiful.
On our descent, we chose the longer, less traveled route and barely saw another person. We discovered a hidden waterfall and sat there for a while, just taking it in. Then, as we were getting hungry and looking for lunch, Ziggy pointed to a massive boulder perched 2,000 feet up the mountainside. “Let’s eat lunch up there,” he said.
So we did. It was his call, his moment of initiative, and it was perfect. Sitting on that boulder, sharing a simple meal and looking out over the landscape, I realized this trip had become something bigger than I’d imagined.
Learning to Let Go
Of course, the journey wasn’t without its challenges. At one point, Ziggy was traveling solo to our next destination when the bullet train station’s credit card system suddenly went down. He found himself stranded, trying to figure out how to get cash in a foreign country. I had to step in and help him navigate the situation.
But even moments like these became part of the larger lesson. My job wasn’t to prevent every difficulty or swoop in at the first sign of trouble. It was to let him learn, to let him problem-solve, but to be there when he genuinely needed support.
What impressed me most was watching Ziggy connect with people wherever we went. We’d attend hardcore shows where he’d immediately make friends, and those new connections would tell us about another show in a different city. Our carefully planned itinerary became this living, breathing thing, shaped by the relationships he was building and the opportunities that emerged from his openness to new experiences.
What I Learned from My Son
Throughout the trip, I was struck by Ziggy’s discipline—something that far exceeded what I had at his age. Even while traveling, he’d carve out time to meditate and work out. He approached each day with intention and balance. In many ways, he was teaching me as much as I was guiding him.
His natural ability to connect with people, his willingness to embrace uncertainty, and his thoughtful approach to new experiences reminded me that my role as his father isn’t to shape him into who I think he should be. Instead, it’s to create space for him to discover who he already is.
The Real Journey
Traveling together revealed something I’d always suspected but hadn’t fully understood: it’s one of the best ways to truly get to know someone, including your own children. This trip wasn’t just about experiencing Japan’s culture, food, and landscapes—though all of that was incredible. It was about watching my son step confidently into his independence, forge his own connections, and build community wherever he went.
The experience reinforced a lesson that applies as much to entrepreneurship as it does to parenting: sometimes the most powerful thing you can do is step back, create the conditions for success, and trust the process. My job isn’t to fix or mold Ziggy into some predetermined version of himself. It’s to love him unconditionally and support him as he discovers his own path.
As we returned home, I realized that this trip marked not just the end of his high school years, but a new chapter in our relationship—one where I’m learning to be his father in a different way, with more trust and less control.
And through it all, I’ll keep practicing the art of being his dad.