Around the Circle | An Enneagram Channel

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CHAQUE SEMAINE

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.

-2 J

Milton Stewart | President of the International Enneagram Association

In this conversation, Jeff Cook sits down with Milton Stewart—an Enneagram Seven, business leader, and President of the International Enneagram Association (IEA)—for a wide-ranging look at where the Enneagram stands right now and where it’s headed next. Milton shares what the IEA exists to protect: integrity, ethics, and responsible teaching, along with a growing commitment to global community and cross-cultural nuance. They talk about the rise (and fading) of Enneagram “buzz” on social media, the expanding push for scientific credibility, and the difference between trendy typing and real transformation. Milton also tells his personal Enneagram origin story (including his early “mistype everybody I know” phase), how the tool shaped his work in under-resourced education settings, and what it’s like to learn from teachers whose presenceteaches as much as their content. The conversation lands on a core theme: the work—and Milton names two practices that keep it real no matter how much you’ve learned: humility and presence. If you’ve ever wanted a bigger-picture view of the Enneagram world—especially beyond American culture—this one will widen your lens and deepen your hope. 🔗 Links mentioned in the episodeMilton’s website: https://kaizencareers.comMilton’s podcast: Do It For The Gram: Enneagram PodcastInternational Enneagram Association (IEA): https://internationalenneagram.orgIEA Events (“Nine Points”): https://internationalenneagram.org → Nine Points (events posted by accredited professionals)

55 min
-4 J

"Early Access" | Enneagram 5 | Imogen in Shanghai

In this Early Access episode, Katie Whitlock welcomes Imogen, a 24-year-old from Shanghai, China. Imogen shares how she found the Enneagram through a friend, why she identifies as a Five without tests, and how “avarice” shows up as a fierce protection of time, energy, space, and purpose. Together they explore the Five’s impulse to offer information as a form of connection, the tension between deep internal emotion and discomfort with outward emotional exchange, and the relief that comes when the Enneagram gives a framework for accepting difference.

56 min
-6 J

Mistyping Monday | Is Drea a 3, 7, 8 or 1?

Jeff sits down with Drea from Alabama for a fresh round of Mistyping—and what starts as casual catch-up (football fandom, life with a five-year-old, and the chaos of caregiving) turns into a layered conversation about responsibility, control, justice, and self-criticism. Drea shares her story: born and raised in Alabama, married nearly five years, mom to Porter, and currently balancing work as an air compliance specialist with caregiving for her mom, who’s living with early-onset Alzheimer’s with dementia. Along the way, she opens up about finishing her master’s in environmental management, her growing awareness of environmental justice, and what it means to “take up space”—especially after postpartum struggles and a desire to create supportive community for other women.

1 h 10 min
13 FÉVR.

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.

1 h 45 min
11 FÉVR.

"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

54 min
9 FÉVR.

"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.

1 h 15 min
4 FÉVR.

"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
2 FÉVR.

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.

1 h 4 min

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313 notes

Enjoyed

07/11/2025

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!

01/08/2025

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.

31/03/2025

sueub

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

27/03/2025

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.