YPO Retreats

The most powerful retreats go beyond great conversations. They help leaders see themselves differently, confront patterns that may be limiting them, strengthen important relationships, and make meaningful changes in how they live and lead.

Drawing on more than 20 years as a CEO, Jack's executive coaching practice, and the principles of Aliveness Mindset, Jack brings experiential exercises that combine self-awareness, vulnerability, practical insights, and personal accountability.

The goal is transformation: Insights that lead to different choices, stronger relationships, and meaningful action long after the retreat ends.

Retreats to choose from:
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Aliveness Mindset

Defining Question: What brings out the best version of me, and how can I bring more of that person into my everyday life?

Based on Jack's book Aliveness Mindset, this signature retreat helps successful leaders reconnect with what makes them feel fully alive and bring that energy, presence, and purpose into how they live and lead.

Achievement and fulfillment don't always go hand in hand. Leaders can accomplish extraordinary things while losing touch with what makes life most meaningful.

Through powerful stories, reflection, and experiential exercises, participants revisit moments when they felt most alive and discover what those experiences reveal about who they are at their best. They examine the beliefs, habits, and identities shaping their choices and learn to live with greater intention.

Leaders leave knowing what makes them feel alive, who they want to become, and how to bring their best selves to their leadership, relationships, and everyday lives.‍

When leaders are fully alive, the people around them feel it. Their relationships deepen, their leadership strengthens, and their impact expands. 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 can quietly mask the drift.

The Living All In Assessment is a practical, thought-provoking experience that helps leaders honestly evaluate how fully they are living across the

‍Six Pillars of Living All In:

Physical Energy: Your health, vitality, strength, and recovery. Your body is the vehicle for everything else you care about.

Relationships: The depth and quality of your connections with family, friends, and those who matter most.

Work & Contribution: The fulfillment, impact, growth, and meaning you experience through your work and contributions.

Time Alignment: The degree to which your calendar reflects your priorities and how intentionally you invest your time and attention.

Inner Life: Your emotional well-being, self-awareness, curiosity, joy, resilience, and capacity for presence.

Purpose & Meaning: Your connection to values, faith, service, legacy, and something larger than yourself.

The Six Pillars provide a simple but powerful framework for understanding what it means to live a rich, meaningful, and fully engaged life. Rather than focusing on success in a single area, they help leaders see the whole picture and recognize where greater intention will create the greatest impact.

Through guided reflection, meaningful conversations, and practical exercises, participants identify where they are thriving, where they are simply maintaining, and which pillar deserves their attention next.

Built on the principles of the Aliveness Mindset, this experience increases self-awareness, clarifies priorities, and equips participants with practical commitments that align their daily choices with what matters most.

Participants leave with a personal roadmap for Living All In, grounded in the Six Pillars, and a renewed commitment to lead and live with greater purpose, presence, and aliveness.

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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."