A Summer of Transitions, Pilgrimages, Rivers, and Possibility

What my son’s graduation is teaching me about travel, transformation, and why meaningful journeys matter more than ever.

My son Quinn graduates from high school this year and heads off to Cal Poly San Luis Obispo in the fall.

And oh my goodness, it’s been even more emotional than I expected.

Like many parents whose kiddos are standing on the threshold of a new chapter, I find myself feeling a powerful mix of pride, gratitude, excitement, and often wondering how the years have moved so quickly. I was warned by many, but here I am on the other side of it now, warning others. I hope it sticks.

What has struck me most, however, is how little space our culture creates to truly honor these moments.

Don’t get me wrong, we celebrate the achievement. We throw the party. We take the photos. I think I’ve been to 15 graduation parties in the last couple of weeks.

But what I’ve noticed is that they don’t always create the space and grace to acknowledge the deeper transition taking place, for them, for us. The ending of one chapter. The beginning of another. The uncertainty, possibility, responsibility, and growth that come with stepping into a new stage of life.

As I’ve reflected on Quinn’s transition, I’ve realized that this is also something largely missing from travel and even mainstream society.

Me & Quinn on our Tanzania Quest last Summer

Most travel experiences are designed around seeing things, doing things, consuming things, and being entertained. There’s nothing inherently wrong with that. But some journeys have the potential to become something more. They can help us mark important transitions, deepen relationships, reconnect with ourselves, and create space to reflect, honor, and dream about what comes next.

Perhaps that’s why so much of what I’m doing this summer and fall seems to revolve around exactly those kinds of experiences.

And perhaps it’s also because I’m realizing that the ideas we’ve been exploring through the Transformational Travel Council aren’t just concepts for our industry. They’re practices worth living.

This summer, my family and I have the opportunity to do just that. And if this calls to you, whether you're a travel professional or traveler, here’s your invitation to join us.

Whitewater Rafting on the Lower Rogue River

On August 8th, we’ll head to Southern Oregon for a 3-night lodge-based whitewater rafting journey on the Lower Rogue River, one of the places that helped shape me growing up. Jessica, my 16 year old daughter Olive, and Quinn will be joining us as we prepare to turn the page into our next chapter, along with a small group of families and parent-child pairs navigating important transitions of their own. Some are preparing for the move from high school to university. Others are stepping from university into the working world. Some are simply navigating a significant life change.

We’ll spend our days on the river, deeply connecting to nature, our evenings sharing meals, stories, laughs, and creating the kind of environment where meaningful conversations emerge, and real connections are made. We still have room for two more families or parent-child pairs if this sounds like your kind of adventure.

Beginning September 14th, I’ll also be facilitating another cohort of Design for Awe & Wonder, a virtual deep dive for experience designers, tourism professionals, guides, facilitators, and curious travelers who want to better understand how awe, wonder, meaning, and connection can be intentionally cultivated through experiences and mindful practice.

The Kumano Kodo Pilgrimage in Japan

Then, on October 10th, I’ll join my dear friends João and Nuno from Walking Mentorship, Dana Smith, Heather Morse, Victoria Simmons, and an incredible group of fellow explorers on Japan’s Kumano Kodo pilgrimage route. I’m looking forward to spending time with people I admire while walking one of the world’s great pilgrimage trails and exploring what travel can teach us when we move at the speed of our own footsteps. *1 spot left on Oct 10th & 4 spots left on Oct 24th

The more I study travelers and destinations, the more convinced I become that one of the greatest opportunities before us is to intentionally design experiences that cultivate purpose, awareness, meaning, emotional connection, belonging, and positive impact. Not as marketing language, but as real outcomes that matter to travelers, teams, communities, and destinations.

In many ways, all of these threads connect back to the same question: How do we create experiences that help people navigate life’s important transitions with greater intention?

That’s the question I’ll be exploring this season.

I’m curious: what transition, adventure, or possibility is calling you this summer?

And what intention are you bringing into your next season?

Farewell for now,

Jake