Let’s Journey Together
Are you Ready to Walk the Path with me?
Over the years, I’ve come to believe that some of the most meaningful growth and perspective shifts happen when we step outside our normal environments and into experiences that reconnect us to people, place, culture, nature, and ourselves in a deeper way.
The journeys, pilgrimages, gatherings, and retreats I lead are rooted in that belief.
Over the past two decades, I’ve guided teens and parents into indigenous communities with the Maasai in Tanzania, climbed mountains with groups searching for clarity and connection, walked ancient pilgrimage routes, facilitated wisdom and leadership retreats in nature, and convened global gatherings like Transcend Washington, Transcend Slovenia, and the TTC Inner Circle Gatherings.
What connects all of these experiences is a desire to create spaces where meaningful conversation, reflection, challenge, awe, community, and perspective can emerge naturally through shared experience.
These are not simply trips or retreats designed for escape or entertainment. They are invitations to slow down, reconnect, and experience the world and ourselves differently. To step outside the noise and speed of modern life long enough to ask better questions, deepen relationships, expand perspective, and explore what becomes possible when we engage more intentionally with nature, culture, community, and the human experience itself.
Some journeys are adventurous. Some are deeply reflective. Some are professionally transformative. Most become all three.
I’d be honored to share the road with you.
Jake
In the Field
The Kumano Kodō is next. Rafting the Mighty Rogue and another Wisdom Retreat are on the horizon.
August 8–11, 2026
Starting at $2500/pp
Limited space left as of May
Rogue River Whitewater Adventure
For families in transition
While the Rogue River offers an unforgettable outer adventure, this journey is equally about what unfolds within. Guided by Jake Haupert of Explorer X and the Transformational Travel Council, your family will be invited into a thoughtful, facilitated inner experience designed to deepen connection and meaning throughout the trip.
Before launching, Jake will help set intentions, offering simple frameworks and reflective prompts that encourage each participant to consider what they hope to experience — not just on the river, but within themselves and with one another. Along the way, in quiet eddies, around shared meals, and beneath starlit skies, Jake and his family will gently facilitate conversations that invite vulnerability, curiosity, and authentic sharing. Through guided questions, storytelling, and spacious listening, families will explore themes of courage, trust, resilience, gratitude, and growth, all mirroring the rhythm of the river itself.
The rapids become metaphors. The calm stretches become opportunities for reflection. Celebrations, fears, laughter, and even moments of discomfort are welcomed as part of a shared narrative unfolding in real time. This is not group therapy, nor is it overly structured. Rather, it is intentional space held with care so families can bond more deeply, speak more honestly, and listen more fully. By the journey’s end, you will carry home more than memories of whitewater and canyon walls: You’ll leave with strengthened relationships, shared language for meaningful conversations, and perhaps even subtle shifts in perspective that continue long after the river’s current has faded.
Kumano Kodo Pilgrimage
Join me for an 8-day transformative walking journey along Japan’s sacred Kumano Kodo pilgrimage trail, where ancient cedar forests, crystal-clear rivers, and revered shrines invite reflection, clarity, and renewal.
This is not just travel—it’s a chance to slow down, reconnect with yourself, and leave with a clearer sense of purpose and a practical plan to bring your vision into life.
This journey is hosted in partnership with Walking Mentorship, who bring deep expertise in guiding self-development walks in nature.
Dates:
10–17 October 2026 (only 3 of 10 spots left)
Journeys in the Rear View Mirror
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Journeys in the Rear View Mirror ***
Walking the Fisherman’s Trail on Costa Vincentina
Join Walking Mentorship founder João Perre Viana and TTC Co-founder Jake Haupert on ‘The Fisherman's Trail” on Costa Vicentina in Portugal. This is a journey of self-discovery where you can explore your needs, desires, fears, and obstacles that keep you from reaching your potential.
Father & Son Service Adventure in Tanzania
This time in Tanzania will very much be a ‘Rites of Passage’ experience. Fathers and sons will bond through the adventures as well as deep, vulnerable, and meaningful campfire conversations, as everyone there — young and old — approaches key transitions in life in the months and years ahead.