YPO Retreats

With a direct, open, and authentic style, Jack specializes in helping forum members identify what really matters, areas that hold them back, and limiting beliefs, guiding them towards feeling more alive in their work. He encourages action and ensures the journey is enjoyable, providing tangible guidance drawn from real-world examples.

For deep dives (explorations), Jack helps leaders understand the art of discovering the real issue of the presenter. Over 50% of the time, by asking a series of insightful questions, deeper issues surface, leading to more impactful presentations and outcomes.

Retreats to choose from:

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The Aliveness Mindset Retreat: Unleash Your Potential

Based on my book Aliveness Mindset, this exclusive retreat is your opportunity to reconnect with what truly energizes you. It's a chance to achieve peak performance not just in your leadership role, but in your relationships and your life as a whole.

Through a powerful combination of guided reflection, authentic conversations, and practical tools, you'll gain profound clarity on what drives you. You’ll leave with renewed energy, a stronger sense of purpose, and a positive momentum that will be contagious to your team. Imagine inspiring and motivating them to reach their fullest potential, simply by being more intentional, more courageous, and ready to take aligned action.

This isn't just a retreat. It's a complete reset for how you lead, how you live, and how you show up Living All In.

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Beyond Anxiety: Reclaiming Identity, Creativity and Calm

This exercise is based on Martha Beck's book. It challenges leaders to examine their hidden relationship with anxiety, productivity, and work identity. CEOs explore how anxiety may be driving performance while distorting self-worth and shutting down creativity. Through guided reflection, they expand beyond over-identification with their role and reconnect with parts of themselves that foster curiosity, joy, and aliveness. Participants leave with a renewed sense of clarity, practical mindset shifts, and a deeper vision of success that includes purpose without burnout.

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‍Breaking the Age Code: Rewriting the Narrative of Aging and Leadership Longevity‍

Based on Becca Levy’s groundbreaking research, this exercise reveals how age beliefs directly impact health, vitality, and leadership performance. CEOs uncover and challenge internalized stereotypes about aging, explore their own narrative, and reflect on aging role models who inspire strength and creativity. Leaders who embrace positive age beliefs can add up to 7.5 years to their life. This session invites participants to redefine what’s possible in their next chapter and reconnect with the deeper value they bring as they grow older.

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‍Creating An Inspiring 10-Year Life Vision

Engage in a collaborative process to develop an inspiring 10-year life vision that fuels your passion and drive, laying the groundwork for a future filled with achievements and personal satisfaction. This journey invites you to envision a future that not only excites and motivates but also aligns with your deepest aspirations, preparing you for a decade of purposeful progress and fulfillment.

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‍Creating a Happier, More Meaningful Life & Being a Better Friend

"Good relationships keep us healthier and happier. Period." Inspired by the profound insights of Waldinger and Schulz, this exercise draws from "The Good Life," a bestseller grounded in Harvard's 85-year longevity study—the world's longest scientific research on happiness.

Leveraging the findings from this landmark study, our exercise guides you to assess and improve your relationships. It offers strategies to deepen connections and become a more supportive friend, fundamentally enhancing your long-term well-being and happiness.

Defining My Legacy/5 Types of Wealth (New!)

What does legacy mean to you? We'll dive deep into what truly matters beyond professional accolades. While many of us have celebrated impressive growth and success, what do you truly want to be remembered for?

During this transformative exercise, members will engage in heartfelt discussions about their legacies. What are you most proud of? What accomplishments and lessons do you wish to leave behind?

We'll then explore Sahil Bloom's groundbreaking framework for a fulfilling life through the lens of five essential types of wealth: Time, Social, Mental, Physical, and Financial Wealth.
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Members will gain actionable insights and practical strategies to cultivate a more balanced and fulfilling life. You'll leave with a clearer view of your Legacy, and understanding of how to integrate the five types of wealth into your daily routine, empowering you to improve your personal and professional relationships, enhance your well-being, and redefine success on your own terms.

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‍The Enneagram Personality Profile

Explore profound self-awareness with the Enneagram Personality Profile. As a certified facilitator, Jack introduces you to this transformative tool, illuminating your motivations, strengths, blind spots, and areas for growth. The Enneagram reveals your unconscious patterns and their impact on your interactions, providing insights into your personal journey. The Enneagram Personality Profile enables you to enrich your connections, deepening your appreciation for the diverse perspectives of those around you.

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‍The Power of Regret: Using Regret as a Leadership Advantage

This exercise, inspired by Daniel Pink’s work, helps CEOs reflect on regret as a tool for personal and strategic clarity. Participants examine where regret has shown up in their lives, identify the values underneath it, and move from rumination to responsibility. Instead of pushing regret aside, they learn to use it as insight. This process builds self-awareness, compassion, and the courage to lead and live more intentionally going forward.

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‍The 15 Commitments of Conscious Leadership

Explore a leadership model centered on responsibility, curiosity, and integrity with The 15 Commitments of Conscious Leadership. This framework guides leaders to establish meaningful agreements and nurture a culture of conscious leadership. Adopt this transformative approach to inspire accountability, team cohesion, lifelong learning, and respect within your organization.
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A word from Jack: 

"As a seasoned coach and YPO member since 2007, I specialize in empowering CEOs to lead with more clarity and decisiveness, enabling them to unlock their full creative potential. My deep understanding of the unique challenges faced by leaders, derived from years of moderating my own forum, allows me to offer targeted support to those committed to meaningful change and maximum forum impact."

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