YOUR NEXT MOVE
STARTS IN THE GORGE
One night in Red River Gorge at peak fall color — to step outside the pace of leadership and ask the question most founders never make time for.
October 22–23 or October 23-24 • Dappled Light Retreat Center • Red River Gorge, KY • $1,000/seat • Limited Availability
Gain Fresh Perspective
Reconnect with What Matters
Look Beyond the Business
Join a select group of founders and trusted advisors in Red River Gorge for meaningful conversation, reflection, and space to think more intentionally about the next chapter of life and leadership.
THE OPPORTUNITY
Out of Office. Into Nature.
You've given most of yourself to this business. The hours, the decisions, the people who depended on you. But there's a question that comes with everything you've built — one that's hard to ask when you're still in the middle of it: Who am I beyond this? And what do I actually want next?
Most founders don't make space for the question of what comes next until they're already in the transition. This retreat changes that. Forget business casual — come in business comfortable. One night in the gorge to step outside the pace of everyday leadership and do the thinking that makes what comes next feel possible, and worth it.
THE SEttinG
Red River Gorge · Eastern Kentucky
Dappled Light Retreat Center: 50 private acres set above the sandstone cliffs of Red River Gorge. Boutique glamping accommodations — heated tents with a real bed and cliff-edge valley views. Far enough from the city to feel like a true departure. Close enough to be practical.
WHO IT’s FOR
Business owners and founders who have built something meaningful
Within roughly 10 years of a transition — whether it's on your radar or not
Not planning an immediate exit — you don't need to be. You just need to be willing to think.
Ready to step outside the pace of leadership long enough to ask the bigger questions
A Jeffersonian dinner — top-tier cuisine, one conversation, every voice heard, no one dominating the table
Guided reflection sessions that help you step outside your role and reconnect with yourself
Structured space to explore what you actually want the next chapter of your life to look and feel like
A guided hike through Red River Gorge at peak fall color — the kind of landscape that makes people think differently
Fireside conversations overlooking the gorge — the boardroom replaced by something worth the view
A bourbon and wine tasting following dinner — a natural close to a conversation worth savoring
Intentional space to think about life beyond the business — with openness, not urgency
THE EXPERIENCE
WHAT CHANGES
A clearer answer to the question you haven't had space to ask — what do you actually want next?
A sense of self that isn't defined by your title, your revenue, or what the business needs from you
Relationships with people who understand this season of life — not colleagues, not family, but peers who've been here
The kind of clarity that usually only comes from a major life event — arrived at intentionally, instead
PRICING
Your investment to Join
$1,000
Per seat. ONE NIGHT. Limited availability.
Glamping accommodation included.
Select Cohort 1 (Friday) or
Cohort 2 (Saturday) at registration.
Also interested in Eureka! Ranch in August?
Ask about the two-event path.
Frequently Asked Questions
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Clearing the Way to What’s Next is a private two-day retreat for business owners and trusted advisors focused on meaningful conversation, reflection, future visioning, and exploring life beyond the business with greater clarity and perspective.
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No. While succession and transition may be part of the conversation, this is not a technical exit-planning seminar or transactional event. The retreat focuses more on the human side of leadership transition, identity, future possibility, and what it means to eventually move beyond the operating role.
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Not at all. Many participants are simply beginning to think more intentionally about what the next season of leadership and life could look like.
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The retreat was designed for founders and business owners who have spent years building and leading something meaningful and want space to think more intentionally about leadership, succession, freedom, and the future.
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The retreat is designed to create a different kind of conversation between founders and the advisors they trust most. Rather than transactional discussions, the experience creates space for deeper reflection, understanding, and future-focused dialogue through shared experience.
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Over two days, participants will engage in:
guided reflection
future visioning exercises
fireside discussions
small-group conversations
reflection hikes
shared meals
quiet time in nature
and a Jeffersonian-style dinner conversation
The experience is intentionally conversational, reflective, and relational.
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The retreat is intentionally small, with an intimate group of founders and 4–6 trusted advisors participating.
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The retreat takes place at Red River Gorge’s Dappled Light Retreat Center, a private retreat property surrounded by forest, hiking trails, cliffside views, and quiet natural landscapes.
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Dappled Light Retreat Center is designed to feel more like a thoughtfully curated outdoor retreat experience than a traditional conference venue. The property includes glamping tents, cabins, wooded trails, gathering spaces, fire pits, cliffside views, and quiet areas for reflection across 50 private acres.
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Participants stay in double occupancy glamping tents or cabins designed to be comfortable, restorative, and connected to nature. Accommodations include real beds, electricity, heating and cooling, bathhouse access, and thoughtfully designed gathering spaces.
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Yes. While there are shared experiences throughout the retreat, the overall pace is intentionally spacious. There will be time for quiet reflection, walks, informal conversation, and rest.
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Comfortable, casual clothing appropriate for fall weather and light outdoor activity. Think relaxed retreat atmosphere rather than business conference.
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The retreat is intentionally designed to help participants disconnect from the pace of everyday leadership. Wi-Fi is limited or unavailable in some areas of the property.
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Shared meals are included throughout the retreat experience, including a Jeffersonian-style dinner designed to encourage meaningful conversation and connection.
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Not very. Optional reflection hikes and outdoor experiences are designed to be accessible and restorative rather than strenuous.
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The retreat is hosted by Chris Evans and Lisa Bosse of The Founder’s Transition Lab.
Chris Evans is a 3-time founder, executive coach, and transitions specialist. Lisa Bosse is a Certified Exit Planning Advisor and executive coach serving founders and family businesses. -
Participants often leave with:
greater clarity about what matters most
fresh perspective on leadership and the future
deeper self-awareness
more meaningful conversations
and a clearer sense of what they may want the next chapter of life to look and feel like
YOUR GUIDES
Lisa Bosse is a Certified Exit Planning Advisor and executive coach serving founders and family businesses. Chris Evans is a 3-time founder, executive coach, and transitions specialist.
Lisa Bosse
Certified Exit Planning Advisor and Executive Coach serving family businesses
Lisa has spent over 20 years guiding the personal and professional transitions of family business owners, succession teams, and growth-stage leaders. She brings deep insight into founder psychology, family business dynamics, and long-view leadership—and a calm, thoughtful presence that helps founders think clearly through complexity.
Chris Evans
Executive Coach and Transitions Specialist,
3-Time Founder
Chris has built and exited three businesses and now helps seasoned leaders navigate identity shifts, big decisions, and purposeful reinvention. He blends decades of entrepreneurial experience with executive transition coaching to support founders in stepping into what’s next with clarity and confidence.