Around the Circle | An Enneagram Channel

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The Enneagram is a map of the human personality. It’s a tool for navigating relationships. It creates language for what motivates us and helps us look at the way we look at everything else. Most importantly the enneagram is a mirror; because sometimes you need help seeing yourself.

1D AGO

Holy Ideas and the High Side of Our Motive | 891s

This is our Second Saturday Workshop from January! Members can sign up for all of our coming workshops : HERE In this conversation, we return to motive—this time on the high side: what it looks like to be your type when you’re grounded, centered, and flourishing (not in stress, not in security). We lay out a simple map for transformation—from our Shadow → through the Holy Idea → awakening our Virtue—and invite real-time reflection from our community on what changes when we begin to trust a bigger reality than our fear. We tackled the body triad—891s—in January. Eights wrestle with Holy Truth and the possibility of innocence without naivety. Nines explore Holy Love, self-worth, and what it means to take up space without losing peace. Ones confront Holy Order, naming resentment, control, and the long journey into serenity, flexibility, and joy. We end by celebrating the gifts that show up on the high side: the Eight’s empowering strength and demand for what’s real, the Nine’s steady presence and non-dualistic wisdom, and the One’s persistent care for justice—turning chaos into order with a deeply rooted heart. Members can sign up for all of our workshops : HERE On February 14th, we will talk through 234s—so bring your heart-triad people and come ready to talk about what “going high” can look like in real life.

1h 45m
4D AGO

"Early Access" | Enneagram 4 | Lucas in Illinois

Continuing the 4 journey, Katie talks to Lucas, a 28-year old musician. They talk acceptance, growing up, and what it feels like to be a male who lives so much of life deep in the feeling center. Find Lucas on Instagram at ofthoughtandfeeling Find Lucas' music on Spotify

53 min
6D AGO

"Inside Story" | Enneagram 7 | Lindsey Davis

Kristin Messegee sits down with Lindsey Davis for a Type Seven installment of Inside Story—and what starts as a “get to know you” quickly becomes a rich, surprisingly tender exploration of how Sevens actually experience their inner world. Lindsey shares the personal upheaval of 2025 (divorce, re-finding herself, and realizing she’d been mistyped as a Two for nearly a decade), and the two of them unpack what changes when you’re finally looking through the right lens: why boundaries can feel hard for different reasons, how reframing works as both a gift and a defense, and what it’s like to feel “a good day” while quietly bracing for it to disappear. Along the way they talk somatic awareness, the body as truth-teller, the “good girl vs good woman” shift, anger as a boundary signal, and even why some Sevens show up publicly for hard topics (like politics) while avoiding the friction one-on-one. It’s funny, honest, and deeply practical—an episode for anyone trying to build self-trust, tell more of the story, and stay present when life gets complicated.

1h 15m
FEB 4

"Early Access" | Enneagram 4 | Jeremy from Texas

In this Early Access conversation, Katie sits down with Jeremy (“Remy”), an Enneagram Four from Texas whose life has moved through music, church work, divorce, and the long aftershocks of abandonment. Together they get underneath the classic Four questions—wanting to be “not misunderstood,” protecting a kind of mystery, and carrying a quiet fear that people will leave once they’ve seen too much. Jeremy tells the story of watching his father hand his mother divorce papers in kindergarten, then later losing his job, his mother, and his marriage—experiences that shaped both his intensity and his caution. From there, the episode pivots into healing: what it means for Fours to realize they’re already “glorious,” to stop chasing constant extraordinariness, and to learn how the ordinary can still hold real beauty. The conversation also gets timely, exploring how social media and algorithm-driven platforms raise the threshold for what feels meaningful—flattening art, attention, and even identity into “what will perform.” Jeremy offers a grounded, artist’s critique of the attention economy, and Jeff closes by teeing up a part two—because they only scratched the surface of Jeremy’s story.

49 min
FEB 2

Mistyping Monday | Collin from Albuquerque | 1, 2, or 7?

Spoiler! This episode has a surprise ending! Jeff welcomes longtime friend Collin Cannon for a Mistyping conversation that moves easily from friendship into depth. Jeff and Collin explore the tension between Ones, Twos, and Sevens—digging into optimism, duty, anxiety, relationships, and what happens when things break. What emerges is a thoughtful, honest exchange about motive, freedom, and care, leaving listeners with a clearer picture of Colin and a felt sense of how real Enneagram work unfolds in conversation.

1h 4m
JAN 28

"Early Access" | Enneagram 4 | Delian from New York

In this Early Access conversation, Katie Whitlock sits down with Delian, a creative Enneagram Four from upstate New York’s Finger Lakes (which she calls “the speakeasy of New York”)—and the two of them immediately turn a “re-record” into a surprisingly rich deep dive. Delian shares her four-ish world: running a classic car shop with her husband and mother-in-law, pursuing acting, and writing new Enneagram-inspired poetry that blends fantasy, core wounds, and even Greek mythology retellings. From there, the conversation moves into the messy, honest terrain of typing: why Delian first tested as a Two, flirted with being an Eight (because wouldn’t it be nice to be action-forward?), and only felt fully “seen on the page” when she discovered the self-pres Four subtype. Together they unpack the difference between stress and excess, the role of time orientation, and why gender expectations can shape how “thinking” shows up in Fours and Fives. The heart of the episode lands on shame, significance, and the Four’s tension between longing for authenticity and using “brokenness” as an excuse to delay real life. It’s warm, funny, personal—and quietly brave.

1h 4m
JAN 27

"Inside Story" | Enneagram 6 | Kristin Messegee

Kristin Messegee flips the script on Inside Story and lets herself be the Six, handing the interviewer role to Jeff Cook. They dig into how Sixes read strength, why reliability feels magnetic, and what “pushing against” someone really means when you need the ground to hold. We talk about triggers, control, and the specific places anxiety shows up—her husband’s health, her kids, her work, and a divided world that fuels her distrust of groupthink and institutions. They talk about unproductive thinking, why encouragement often doesn’t land, and what actually helps: interrupting the spiral through the body, regulating the system, and building an internal voice that stays kind and steady. Along the way: independence as freedom (hello, car rides), “escape” as an eject button, and a funny, skeptical detour into AI and certainty.

1h 26m
JAN 22

Misconceptions about Eights

Connect with our material HERE Connect with Stacey HERE Jeff Cook sits down with coach, author, and deconstruction theologian Stacey Wynn to clear up common misconceptions about Enneagram Eights—and name what often gets missed about their inner life. Stacey talks about being labeled “intimidating,” why many Eights aren’t loud bullies, and how they often “fill the vacuum” when leadership lacks integrity. They explore the Eight’s small circle of trust, how Eights can care deeply (and sometimes “care aggressively”), and how anger functions less as outbursts and more as a steady internal signal—especially around dismissal, betrayal, and justice. The conversation also touches fear, control, and “decisioning,” plus the Eight-Five dynamic in relationships. They close with a brief turn toward theology and deconstruction, focusing on power, hierarchy, and healthier communities, and Stacey shares where listeners can find her work.

1h 1m

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4.9

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313 Ratings

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11/07/2025

Afstrick2013

I searched on a long shot when husband exclaimed he wanted to hear more ‘1s’, but it was easier listening to a man’s voice. As the one, I feel like Jeff did a great job “laying us out”. I look forward to checking out his number shows, 5. Thank you!
Enneagram as it’s meant to be!

08/01/2025

LGT33

Jeff and TJ take enneagram to the depths it was intended to go! They also provide a platform for so many enneagram voices and facilitate such rich conversations!
Best enneagram podcast available.

03/31/2025

sueub

Thanks guys for all the hard work. I do love this podcast.
5 stars!

03/27/2025

AllyNoel

I love this podcast. It’s easy to listen to and extremely interesting. I love getting different perspectives and relatable references. The guests are also people I familiar with so that makes sense even more tantalizing.

The Enneagram is a map of the human personality. It’s a tool for navigating relationships. It creates language for what motivates us and helps us look at the way we look at everything else. Most importantly the enneagram is a mirror; because sometimes you need help seeing yourself.