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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Aliveness Mindset

Defining Question: Am I living each day fully and at my best?

Based on my book Aliveness Mindset,this signature retreat helps leaders reconnect with the internal state that fuels their greatest fulfillment, resilience, and impact.

Many successful leaders have mastered achievement. Fewer have intentionally developed the person they are becoming while carrying the weight of leadership.

Through powerful stories, guided reflection, meaningful dialogue, and experiential exercises, participants examine the beliefs, habits, and identities that shape their lives. They discover what makes them feel fully alive, identify what quietly pulls them away from it, and learn a practical framework for living and leading with greater intention.

Leaders leave with renewed energy, deeper self-awareness, greater presence, and a clearer vision of the person they want to become.

When a leader is fully alive, their team feels it, their culture reflects it, and their impact multiplies. This is Living All In.‍

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Living All In: A Life Assessment

The Defining Question: How am I living across the areas of life that matter most?

Many leaders build remarkable careers while slowly drifting from the people, priorities, and experiences that matter most. Success often hides the drift.

The Living All In Assessment is a practical reflection that helps leaders honestly evaluate how fully they are living across the areas of life that matter most.

Participants explore six dimensions of a meaningful life, identify where they are thriving, where they are simply maintaining, and where intentional change will have the greatest impact.

Through structured reflection and group discussion, leaders gain greater self-awareness, sharpen their priorities, and develop practical commitments that align their daily lives with what matters most.

Built on the principles of the Aliveness Mindset participants leave with a clearer picture of their current reality and a roadmap for Living All In.

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Leading All In: A Leadership Assessment

The Defining Question:How am I leading, and who does my team need me to become?

‍The best leaders don't become exceptional by accident. They become intentional.

‍Leading All In is an executive leadership reflection that helps leaders step back from the demands of leadership and examine how they lead themselves, how they lead others, and the legacy they're creating every day.

Through guided reflection and meaningful dialogue, participants explore their purpose, presence, courage, ownership, decision-making, ability to develop others, and the choices that shape their leadership. Rather than measuring leadership competencies, the experience helps leaders become more intentional about the leader they are becoming.

Leaders leave with greater clarity, practical commitments, and a personalized roadmap for leading with greater courage, ownership, influence, and lasting impact.

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‍Boy, Beast, King/Girl, Protector, Queen

Successful leaders don't struggle because they lack intelligence or experience. They struggle because they often don't recognize which inner voice is driving their decisions.

‍Through powerful storytelling, guided reflection, and meaningful discussion, this transformative experience helps participants recognize the three inner voices that shape every decision: the Boy, Beast, and King, or the Girl, Protector, and Queen, and develop the awareness to choose responses that create stronger leadership, deeper relationships, wiser decisions, and a more fulfilling life.

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‍The Drama Triangle

The Drama Triangle reveals the unconscious roles people step into under stress: Victim (powerless), Villain (blame), and Hero (overfunctioning and rescuing).

These patterns often feel justified in the moment, which is why they are so easy to miss. A leader may rescue instead of empowering. A team may blame instead of taking ownership. Someone may feel stuck, waiting for others to change. The result is predictable: reactivity increases, energy drains, and the same problems keep repeating.

This exercise helps you identify your default pattern and recognize how it shapes your leadership, communication, and relationships. With awareness comes choice.

Instead of operating from drama, you learn to shift into a Creator mindset - taking ownership, focusing on what you can control, and moving toward clear action.

The result: less blame, stronger accountability, better decisions, and more intentional leadership at work and at home.

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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."