Around the Circle | An Enneagram Podcast

Latest Episodes:

A Scientist and a Philosopher III | Quality Enneagram Knowledge? Aug 20, 2026

Show notes

Dr Sam E Greenberg and Prof Jeff Cook take to the mics again, this time to talk about high quality Enneagram study: where’s the best work being done, what counts as knowledge, and do those learning about Enneagram have access?

They spend the first 30 minutes talking about broad issues in epistemology and contemporary media, but pivot to Enneagram world and work through the needs and discoveries of our community.

Fresh Thoughts on Spiral Dynamics and The Enneagram Aug 16, 2026

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This episode introduces Spiral Dynamics as a framework for understanding human maturity, the values that shape us, and the predictable transitions we experience throughout life.

Jeff connects Spiral Dynamics with the Enneagram, asking how our stage of development influences what we seek from the Enneagram, how we understand our type, and ultimately what we believe the Enneagram is for.

In Conversation with 5s, 6s & 7s | An Enneagram Coach Series Aug 13, 2026

Show notes

Join us September 12 for our discussion with 891s by signing up for a membership : HERE

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What do Enneagram Fives, Sixes, and Sevens actually share?

In this Second Saturday workshop, we sit down with three Enneagram coaches to explore the Head Types—moving beyond stereotypes and returning to some of the basics that aren't so basic : featuring Kristin Messegee (6), Jackie Brewster (7), and Nadia Rae Brackett (5).

We talk fear versus anxiety, the search for safety and certainty, our relationship with thinking, the emotional lives of the Head Types, and what it means to become more present to ourselves. Along the way, we explore how Fives, Sixes, and Sevens can be reaching for something similar while using remarkably different strategies to get there.

#Enneagram #Enneagram5 #Enneagram6 #Enneagram7 #AroundTheCircle

Enneagram Misconceptions | The Morning Show Aug 11, 2026

Show notes

What if some of the most familiar Enneagram descriptions are actually getting in the way?

In this episode of The Morning Show, Jeff, TJ, Jackie, and Kristin take aim at the stereotypes that flatten the nine types into easy labels: Eights are challengers, Nines are peaceful, Ones are perfectionists, Twos are helpers, Sevens are happy, and Sixes are afraid.

Which stereotypes contain a piece of truth—and which fundamentally misunderstand the type? The crew digs beneath behavior to motivation, exploring why archetypes can be useful, why labels can be misleading, and how popular Enneagram language may actually contribute to mistyping.

It’s a lively, occasionally combative attempt to move beyond the memes and recover something deeper.

#Enneagram #EnneagramTypes #Personality #SelfAwareness #AroundTheCircle

Shame and Guilt | "Atlas of the Heart" | Chapter 8 Aug 09, 2026

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JOIN US ON TUESDAY NIGHTS : HERE

What happens when falling short becomes a verdict about who we are?

In this episode of the Reading Room, Jeff continues through Brené Brown’s Atlas of the Heart, exploring shame, guilt, humiliation, embarrassment, perfectionism, and self-compassion. We look at Brown’s distinction between “I did something bad” and “I am bad,” why empathy can disrupt shame, and how perfectionism can turn achievement into a measure of our worth.

The conversation also pushes into Enneagram territory: Do different types experience shame differently? When does healthy striving become perfectionism? And if we are not what we accomplish, where should we locate our value?

A conversation about failure, empathy, connection, achievement, and learning to make room for being imperfect.

#Enneagram #BreneBrown #AtlasOfTheHeart #Perfectionism #Shame

Boundaries and Empathy | A Discussion of "Atlas of the Heart" Chapter 7 Aug 06, 2026

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Join us on Tuesdays : HERE

What does it actually mean to empathize with someone? And how is that different from compassion?

In this Reading Room discussion on Brené Brown's Atlas of the Heart, we explore empathy, compassion, boundaries, and the Enneagram. Together, we wrestle with why some of us instinctively fix, others merge, and others withdraw—and how each type can grow in learning to truly be present with another person's suffering.

#Enneagram #BreneBrown #Empathy #Compassion #ReadingRoom

Empathy and Compassion | "Atlas of the Heart" | Chapter 7 Aug 03, 2026

Show notes

Join us on Tuesdays : HERE

Empathy is harder than we think.

In this episode of Reading Room, Jeff continues through Chapter 7 of Brené Brown's Atlas of the Heart, exploring the emotional landscape of compassion, empathy, pity, sympathy, boundaries, and comparative suffering.

Along the way, Jeff connects Brown's research with Aristotle, Wittgenstein, Buddhist thought, and the Enneagram, asking what it actually means to accompany another person in pain without trying to fix, rescue, or distance ourselves from them.

The conversation explores why empathy is a skill rather than an instinct, why compassion requires both courage and restraint, how pity and sympathy quietly undermine connection, and why healthy boundaries are an essential part of loving others well. Jeff also reflects personally on how these themes challenge him as an Enneagram One and considers whether genuine maturity requires moving from individual achievement toward shared human experience.

Join us for the live Reading Room discussion each Tuesday at AroundtheCircle.org

#AtlasOfTheHeart #BreneBrown #Empathy #Compassion #Enneagram

When Your Body Stops Cooperating | Brenden Wynn (6) Jul 30, 2026

Show notes

Jeff Cook and TJ Wilson are joined by Brendan, an Enneagram Six living with chronic pancreatitis, chronic pain, PTSD, and life after a total pancreatectomy.

Alongside TJ's experience with fibromyalgia, they explore how chronic illness interacts with Enneagram type, revealing why two people facing similar pain can respond in profoundly different ways.

Together they discuss the invisible burden of chronic illness, the struggle to be believed by doctors and loved ones, how different personality types advocate for themselves (or don't), and why pain so often compounds our deepest patterns of fear, responsibility, identity, and control. The conversation also explores work, marriage, shame, recovery, grief, and the difficult process of accepting a "new normal" when life cannot return to what it once was. Along the way, they offer hope through meaningful connection, mindfulness, movement, and the possibility that understanding ourselves can help us navigate suffering with greater compassion.

Connect with us at aroundthecircle.org

#Enneagram #ChronicIllness #ChronicPain #MentalHealth

"Unwanted Identity" | The Morning Show | Part II Jul 28, 2026

Show notes

"It's important that I'm not perceived as..."

The answers uncover the hidden identities each type works to protect—from the Four's fear of being ordinary or misunderstood, to the Three's struggle with competence and authenticity, the Two's desire to remain indispensable and easy to love, and the One's deep concern with integrity, intention, and being seen as fundamentally good.

We are wrapping up our dive into the experiences of shame for 4s, 3s, 2s, and 1s.

#Enneagram #Shame #BreneBrown #SelfAwareness #PersonalGrowth

Hope and Grief | "Atlas of the Heart" | Chapter 6 Jul 26, 2026

Show notes

Connect with us: HERE

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Hope. Courage. Grief. Longing.

Continuing through Brené Brown's Atlas of the Heart, Jeff explores what happens when suffering changes not just how we feel, but how we imagine the future. Why does despair convince us tomorrow will look exactly like today? Why is being unseen in our suffering one of the loneliest human experiences? And why does returning to our center matter so much when life becomes disorienting?

At the heart of the discussion is a simple conviction: hope is not naïve optimism. It is the fuel that gives courage something to run on—and perhaps the beginning of every meaningful recovery.

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