In the Field
Come Explore What You Can Become
Over the years, I’ve come to believe that some of the most meaningful growth and shifts in perspective happen when we step outside our usual environments and reconnect with people, place, culture, nature, and ourselves.
The journeys, pilgrimages, gatherings, and retreats I lead are rooted in that belief.
For more than two decades, I have walked with families, leaders, and communities through experiences shaped by adventure, pilgrimage, reflection, and place. This has included journeys hosted with Maasai partners and communities in Tanzania, mountain and river expeditions, ancient pilgrimage routes, wisdom retreats in nature, and gatherings such as Transcend Washington, Transcend Slovenia, and the TTC Inner Circle Gatherings.
The intention is not to manufacture transformation, but to create conditions where meaningful conversation, reflection, challenge, awe, community, and new perspectives can emerge through shared experience.
Some journeys are adventurous. Some are deeply reflective. Some support professional growth. Most hold space for all three.
I’d be honored to share the road with you.
Jake
Where next …
The Kumano Kodo is next, followed by the Transformative Experiences Symposium in Seattle and another Wisdom Retreat with MEA in Baja.
Kumano Kodo Pilgrimage
Join me for an 8-day walking journey along Japan’s sacred Kumano Kodo pilgrimage trail, where ancient cedar forests, clear rivers, and revered shrines invite reflection, presence, and renewal.
This journey creates space to slow down, notice more, reconnect with what matters, and explore how insights from the trail might carry into everyday life.
It is hosted in partnership with Walking Mentorship, whose team brings deep experience guiding self-development walks in nature.
Dates:
• October 10–17, 2026 (sold out)
April 4th to 11th, 2027
Pre-Nature Walk: April 4 - 6
Symposium: April 6 - 9
Camano Island Research Lab: April 9 - 11
Transformative Experiences Symposium
Seattle, Washington, USA
Travel and hospitality are at a turning point. The Experience Economy reshaped the industry, and communities, travelers, and destinations are now asking deeper questions about meaning, connection, impact, and stewardship.
The Transformative Experiences Symposium brings leaders across hospitality, destinations, experience design, community development, research, conservation, and philanthropy together to explore what comes next.
Across eight days and three connected phases, we will work with one central question:
What conditions, design choices, and economic structures support transformative experiences and full-systems stewardship?
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 Quest 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.