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Burnout shows up in many ways, but at its core it often signals a life out of alignment. Cait Donovan sits down with executive coach and author Jerry Colonna to explore what happens when outward success hides an inner collapse. Jerry opens up about the years he spent chasing achievement as a venture capitalist and how every new milestone left him feeling worse instead of fulfilled. What does it mean when the world applauds your accomplishments but your soul feels heavier with each step forward? And how do we begin to untangle the beliefs that keep us performing long after they’ve stopped serving us?

Jerry shares how radical self-inquiry became a way back to himself. Rather than a process of blame, it is a practice of curiosity, asking questions that cut through guilt and open space for conscious choice. He and Cait reflect on how early coping strategies like perfectionism may once have offered safety, yet can slowly erode well-being over time. They also look at the role of privilege and access in recovery, naming the tension between personal agency and systemic limits.

Jerry’s story of “Grandfather Boulder” is a reminder that listening itself can be an act of healing. Could paying attention to our own pain, to each other, to the systems around us, the beginning of change? This episode invites you to consider what alignment looks like in your own life and how the ongoing work of inquiry can open the door to both resilience and growth.

Episode Breakdown:

00:00 Welcoming Jerry Colonna

02:39 Jerry’s Burnout Story and Misalignment

08:03 Financial Success and the Burnout Trap

16:17 Radical Self-Inquiry as a Path to Healing

24:00 Choosing Life in the Depth of Burnout

30:06 Rewiring Beliefs and Making Conscious Choices

40:30 Personal Growth as an Act of Resistance

46:23 Grandfather Boulder and the Power of Listening

Links

Reboot: Authentic CEO Coaching and Leadership Development

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