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: Lead and Live Fully Alive

Based on my book Aliveness Mindset,  this retreat helps leaders reconnect with the internal state that fuels their greatest performance, fulfillment, and impact. Most CEOs have mastered achievement. Few have mastered aliveness.

Through guided reflection, powerful group dialogue, and experiential exercises, you will identify when you feel most alive and what has pulled you away from it. You will clarify the mindsets, choices, and actions that restore energy, purpose, and presence.

Leaders leave with renewed clarity, deeper alignment, and the ability to lead from conviction rather than pressure. This is leadership development at the identity level. When a leader is fully alive, their team feels it, their culture reflects it, and their impact multiplies. That’s Living All In.

This retreat creates a reset in how you lead, how you relate, and how you live.

Defining Your Legacy Through the Six Types of Wealth

Professional success alone does not define a meaningful life. This exercise (based on Sahil Bloom’s The Five Types of Wealth) helps leaders clarify the legacy they want to create across all dimensions of wealth.

Using the Six Types of Wealth framework, leaders explore:

• Time Wealth: Freedom to spend your time intentionally
• Social Wealth: Depth and quality of relationships
• Mental Wealth: Clarity, growth, and emotional resilience
• Physical Wealth: Energy, vitality, and health
• Financial Wealth: Security, freedom, and opportunity
• Spiritual Wealth: Purpose, meaning, inner peace, and connection to something greater than yourself

Through guided reflection and group dialogue, leaders identify where they are strong, where they are depleted, and what changes will create a more integrated and fulfilling life.

We place additional attention on Social Wealth, and add insights from The Good Life, which is based on Harvard’s 85 year Study of Adult Development, the longest scientific study on happiness. The study found that the single greatest predictor of long-term happiness, health, and longevity is the strength of your relationships.

Leaders assess their most important relationships, identify where they want to invest more deeply, and clarify how they want to show up as a partner, parent, friend, and peer. Strong relationships provide meaning, resilience, and fulfillment that no level of professional success can replace.

Participants leave with clarity on their legacy and concrete actions to build true wealth across all six dimensions.

‍Boy, Beast, King/Girl, Protector, Queen

This powerful framework helps leaders understand and integrate the core energies that shape how they lead and live. The Boy and Girl represent curiosity, openness, creativity, and emotional honesty. The Beast and Protector embody instinct, courage, drive, and the ability to set clear boundaries. The King and Queen reflect responsibility, vision, and stewardship in service of others.

Each part has inherent value. Leadership maturity comes from accessing all of them intentionally and in balance. When overused or expressed unconsciously, each can become unhealthy. The Boy or Girl may avoid responsibility or seek approval. The Beast or Protector may become reactive, controlling, or aggressive. The King or Queen may become rigid, disconnected, or overly identified with status or authority.

This exercise helps leaders recognize these patterns, integrate the healthiest expression of each role, and lead with greater presence, strength, authenticity, and wisdom.

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Make Your Partner Feel Like a Priority

High-performing leaders bring intention, discipline, and accountability to every area of life. This exercise applies those same principles to their most important relationship.

Grounded in Gottman’s research, participants recognize early warning signs and identify the specific ways their own behavior, attention, and habits impact the level of connection with their partner.

Each leader makes a clear, measurable commitment that makes their partner tangibly feel like a priority, with the accountability of their forum to follow through.

The result is deeper connection, stronger trust, and greater fulfillment at home.

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Breaking the Age Code:
Redefining Leadership and Vitality in Your Next Chapter

Based on the research of Yale psychologist Becca Levy, this exercise reveals how beliefs about aging directly influence vitality, health, and leadership effectiveness.

Leaders examine their internal narrative about aging and its impact on their energy, ambition, and future. They explore role models who demonstrate vitality and creativity later in life and redefine what is possible in their next chapter.

This experience helps leaders access greater energy, confidence, and purpose while embracing the wisdom and perspective that come with experience.‍

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The Enneagram:
A Powerful Tool for Self-Awareness and Leadership Growth

The Enneagram is a personality test that reveals the unconscious patterns that drive leadership behavior, decision-making, and relationships.

Leaders gain insight into their core motivations, strengths, blind spots, and stress patterns. They learn how their personality structure shapes their leadership style and where growth unlocks greater effectiveness.

This experience builds self-awareness, emotional intelligence, and the capacity to lead with greater clarity, flexibility, and impact. It is one of the most powerful tools that I use in my coaching practice. I use it with every client and every team. 
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‍The Power of Regret:
Turning Regret Into Clarity and Leadership Growth

Regret contains powerful insight when examined intentionally. This exercise, based on Daniel Pink’s bestselling book, helps leaders identify meaningful regrets, understand the values beneath them, and use that insight to guide future decisions.

Rather than avoiding regret, leaders learn to use it as a tool for clarity, responsibility, and growth.

Participants leave with a deeper sense of self-understanding and the confidence to lead and live with greater intention.
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Beyond Anxiety: Reclaiming Identity, Creativity, and Inner Calm

Many high-performing leaders have built extraordinary success while being quietly driven by anxiety. This exercise helps CEOs examine the hidden relationship between anxiety, achievement, and self-worth.

Through structured reflection, leaders identify how anxiety has fueled performance while constraining creativity, presence, and fulfillment. They reconnect with parts of themselves beyond their role and rediscover curiosity, creativity, and calm.

Participants leave with practical mindset shifts and a more sustainable internal foundation for long-term leadership success, one driven by clarity and purpose rather than pressure.

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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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