How can changing our relationship to pain transform our lives? In this reflective episode, Jerry is joined by George Loewenstein, Professor of Economics and Psychology at Carnegie Mellon University and author of the book The Opposite of Happiness. Alongside meditation teacher and author Sharon Salzberg, they explore the roots of human misery, blending insights from behavioral economics, psychology, and Buddhist wisdom.

They share honest stories about depression, insights into why our "feelings about feelings" can be so overwhelming, and why hope isn't always as helpful as we think. Sharon brings a Buddhist perspective, breaking down ideas like the "second arrow" and wise hope, while George shares fascinating findings from his research on how we relate to pain and how we get stuck, or unstuck.

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Who we are as leaders is shaped by the stories we carry and the environments we've experienced. In this deeply heartfelt and introspective episode, Jerry is joined by Pam Manfredo Curtis, CEO coach and author of The Origin of a Leader. With a career spanning 35 years and a PhD in industrial-organizational psychology, Pam Manfredo Curtis brings wisdom earned from coaching executive teams across industries and a personal journey rooted in family conversations, empathy, and resilience.

Together, they unpack how our childhood environments and formative experiences shape the belief systems and blocks we carry into adulthood and leadership. They explore the crucial role of psychological safety, the importance of self-inquiry, and why authentic connection and "referent power" matter. Drawing from both personal stories and client examples, they reflect on why radical self-inquiry and the ability to express our truths matter so deeply—especially for those with organizational power.

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How you care for yourself as a coach deeply influences the quality and impact of your work. When we carve out space to reflect on the emotions and patterns coaching activates within us, we open pathways to deeper presence, connection, and transformation—both for ourselves and those we serve.

In this episode, Jerry Colonna and Liz Stewart dive into the heart of coaching supervision: what it is, why it's vital, and how it differs from mentoring. They highlight some of the unseen burdens coaches carry, the importance of having a reflective practice, and the sacredness of creating genuine, ethical relationships with clients. They remind us that supervision isn't just about staying current or professional; it's about self-knowledge, healing, and love.

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What lies beneath our drive for money and success? Is it really about safety, or are we chasing something formed in our earliest years? In this episode, Jerry Colonna is joined by Michelle Masters, author of Wired for Money, as they explore how childhood experiences and inherited patterns shape our adult relationship with money, self-worth, and belonging.

With candor and compassion, Michelle shares stories from her work with clients, including billionaires who still feel anxiety, and explains why our deepest money issues can't be solved by intellect alone. Together, they illuminate how lasting change comes from tending to the subconscious and somatic origins of our beliefs, allowing us to transform money from a source of fear to a blessing.

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What does it take to create truly transformational workplaces, especially when performance management so often feels transactional or disconnected?

In this episode, Jerry sits down with Angela Mckenna, newly appointed coach at Reboot and a veteran in HR, executive leadership, and organizational development. Angela shares wisdom drawn from years inside high-growth companies, examining why performance management is often so challenging and how organizations can move toward deeper clarity, honesty, and engagement.

Together, Jerry and Angela explore the essential role of transparency, skilled managers, and genuine conversations in building cultures where people thrive. She reflects on how workplace dynamics are evolving in the wake of the pandemic and amid the rise of AI, challenging leaders and employees alike to consider what constitutes a truly meaningful and reciprocal workplace contract.

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What does it mean to truly be "okay with being okay?" For many of us, the pursuit of growth, success, and improvement is relentless, often leaving little room for simply accepting ourselves as we are. But what if the real work of adulthood is learning to quiet the inner gremlins, embrace our own enoughness, and build belonging from the inside out?

In this episode, Grace Belangia joins Jerry on the podcast for a second time to discuss rejection, self-worth, and the courage to create community. Together, they explore the importance of building one's own table of belonging and how courageous conversations can transform both our inner and outer worlds.

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What does it mean to be responsible to suffering, not just the pain we carry within ourselves, but the vast, daily hurt we witness in the world around us? In this rich continuation, Jerry is joined by two dear friends, Sharon Salzberg and Parker J. Palmer, to explore our collective responsibility to one another in fractured times.

Together, they examine how the root of so much suffering, personal and systemic alike, lies in our refusal to acknowledge the truth of our interconnection. When we turn away from that truth, we don't escape pain; we deepen it. But when we find the courage to move toward what frightens us, to walk into otherness rather than away from it, something remarkable becomes possible: we begin to discover that there is no Other.

Rooted in Buddhist wisdom, Quaker spiritual tradition, and decades of lived experience, Jerry, Sharon, and Parker reflect on the role of fear in keeping us apart, the necessity of community in doing this work, and the profound animating power of legacy. Of asking not just who we are now, but what kind of ancestors we are becoming.

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When life upends our expectations, the space between what was and what's next—the neutral zone—can feel like wilderness. It's a time of uncertainty, discomfort, and profound possibility. Yet, how we navigate these transitions shapes not just the trajectory of our personal lives, but the culture and resilience of our organizations.

In this episode, Ray Foote joins fellow Reboot Coach Ali Schultz for a deep exploration of the Neutral Zone, drawing from William Bridges' classic framework on change and transition. Together, they reflect on their own experiences and share what it really means to metabolize transition at the organizational and human level.

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