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Guest:

Eldra Jackson III is the Co-Executive Director of Inside Circle, a nonprofit dedicated to breaking the cycles of incarceration and violence through healing-centered inner work. But what makes his experience essential is that Eldra doesn’t just lead this work—he lived it.

He spent 24 years in prison for robbery and attempted murder, including years in solitary confinement. It was in that extreme isolation that Eldra began the transformational work that would change his life—and now impacts countless others.

Since his release, he’s become a national voice in trauma-informed care, restorative justice, and men’s emotional wellness. He’s a TEDx speaker, the subject of the award-winning documentary The Work, and has been featured by NBC News, Forbes, and the LA Times. He also hosts the Inside Circle podcast, where I was honored to join him earlier this year..

About the Episode:

Whether you're designing policy, leading a team, or simply seeking deeper understanding —this conversation will challenge you, move you, and equip you with new insight. In this raw and deeply personal conversation, Eldra takes us through his journey through trauma, transformation, and the hard truths behind incarceration in America. We begin by exploring Adverse Childhood Experiences (ACEs) and how untreated trauma in early life can lead to lives marked by crime, apathy, and pain. Eldra offers a rare, firsthand look at the psychology of gang culture, the pursuit of power, and the deep role that fear and survival play in shaping identity and behavior. We dive into big, systemic questions: Should prison be punitive, rehabilitative, or something else entirely? What do most political leaders misunderstand about human behavior and the roots of violence? And if Eldra had the power to wave a magic wand, what would he do to reduce crime and incarceration by 80% tomorrow?

We discuss the structure and philosophy behind "circle work," the transformative group healing practice that Eldra now facilitates with incarcerated and formerly incarcerated men, the nature of toxic masculinity, the resistance many men feel toward emotional vulnerability, and what it actually takes to undo that conditioning. Perhaps most powerfully, Eldra shares the daily practices and mindsets that keep him grounded and in service to others. This episode is straightforward, surprising, and ultimately hopeful—a powerful reminder that real transformation is possible, not just for individuals, but for systems.

Key Topics Discussed:

· [00:02:40] Guest/Episode Introduction

· [00:06:18] What love means to Eldra

· [00:07:36] Learning to Feel despite Cultural Messaging, and Trauma

· [00:12:22] Sharing for the first time

· [00:14:42] Indoctrinated into Secrecy

· [00:16:10] A Central Unnamed Fear

· [00:18:53] Who was "Vegas”

· [00:21:53] Fear motivating aggression

· [00:24:13] What is Gang Culture?

· [00:29:05] The danger in apathy

· [00:30:40] Eldra’s Rock Bottom: Worse than Charles Manson