OUT OF OFFICE AND INTO NATURE
A private retreat for founders and trusted advisors to step back, reconnect, and imagine what’s next.
October 22–23 or October 23-24 • Dappled Light Retreat Center • Red River Gorge, KY
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
For many business owners, the business has shaped not only how they spend their time, but how they see themselves.
After decades of building something meaningful, it can feel difficult to imagine who you are beyond the role you’ve carried for so long.
Yet the ability to step back, reconnect with yourself, and envision what might lie ahead may be one of the most important parts of someday transitioning beyond the business in a healthy and fulfilling way.
THE RETREAT
Clearing the Way to What’s Next helps founders step outside the pace and pressure of everyday leadership long enough to reconnect with themselves and the possibilities that may lie ahead.
CLEARING THE WAY TO WHAT’s NEXT
This intimate two-day retreat brings founders and trusted advisors together for:
meaningful conversation
guided reflection
future visioning
thoughtful connection
and intentional space to think about life beyond the business with greater openness, clarity, and perspective
WHAT CHANGES
Participants often leave with:
renewed perspective
deeper self-awareness
meaningful conversations
stronger relationships
and a clearer sense of what they want the next chapter of life to look and feel like
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.