Around the Circle | An Enneagram Podcast

Latest Episodes:

"Early Access" | Enneagram 4 | Delian from New York Jan 28, 2026

Show notes

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.

"Inside Story" | Enneagram 6 | Kristin Messegee Jan 27, 2026

Show notes

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.

Misconceptions about Eights Jan 22, 2026

Show notes

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.

"Early Access" | Enneagram 3 | Meg the Therapist Jan 21, 2026

Show notes

Connect with Katie : HERE

In this Early Access episode, Katie Whitlock sits down with Meg—32, a Type Three, newly certified as an Enneagram teacher through the Narrative Enneagram, and also a practicing therapist who integrates the Enneagram into her counseling work.

Meg and Katie explore what it actually takes to become certified in the Narrative tradition (typing interviews, guided questions, hosting panels, and learning through lived stories rather than “textbook types”), along with the posture behind it: typing as an offering, not a verdict. From there the conversation turns personal and very Three-specific—how Meg’s “threeness” formed in evangelical spaces where vulnerability and spiritual performance carried social reward, how stage leadership (worship leading) sharpened her instincts, and how the real work isn’t talking about feelings—it’s staying in the body long enough to feel them.

"Mistyping Friends" | Kim from Greeley | 1, 2, 4, or 8? Jan 19, 2026

Show notes

We are doing a second season of our Mistyping series, but this time with people I love.

In this first episode, I sit down with my good friend Kim—an Enneagram skeptic who’s also one of the highest-character people I know.

We talk about why “typing other people” can feel grotesque, what it’s like to teach fifth grade at a Title I school, and how real leadership shows up when you’re willing to speak up, protect kids, and do the work yourself.

Along the way, Kim opens up about optimismboundaries, faith, and the “desert” seasons that refine you—then we use a simple motive-based mistyping chart to explore what’s actually driving her.

Abbey Howe | Enneagram 3 | From Creator to New Parent Jan 15, 2026

Show notes

You can see much of Abby's video work : HERE

And her Substack is up and running : HERE

New motherhood has a way of stripping you down to the studs—and in this conversation, Enneagram coach and YouTube creator Abby Howe (a Three and brand-new mom) tells the truth about what that stripping-down feels like.

We start with the shock of postpartum life for a Three: the death of old expectations, the humbling realities of sleep deprivation, and the slow reordering of priorities from productivity and performance to presence and survival. Abby describes an unexpected gift that emerged in the wreckage—more grace for herself, and a loosening grip on the old equation of worth = output.

From there, we trace Abby’s Enneagram origin story (including an early “you’re an Eight” mistype), the moment she read The Road Back to You and recognized herself with tears, and how her comedic sketch background turned into a surprising vocational lane: making Enneagram content that helps people say, “That’s me,” and “That’s my partner.” We talk about the tension between fun entry points and stereotype fatigue, and why laughter and self-recognition often open the door to deeper work.

We close with a rich discussion of burnout and restoration—what “getting off stage” can look like for Threes, why healthy Nines can feel like oxygen, and how rest isn’t a failure … it’s part of the work.

Coming in 2026: Abby’s new book, My Enneagram, a visual guide/workbook for finding your type—built around burnout recovery, restorative rest, and growth/stress arrows.

"Early Access" | Enneagram 3 | Emi from Louisville Jan 14, 2026

Show notes

Katie talks to Emi, a local friend who is also a 3!

We talk about what it feels like to present only your best self, slowing down, and the benefits of joining enneagram spaces.

"Inside Story" | Enneagram 5 | Saleh Vallander Jan 12, 2026

Show notes

You can find all of Saleh Vallander's books : HERE

In this episode of Inside Story, host Kristin Messegee sits down with Saleh Vallander—Sweden-based doctor, meditation teacher, and Enneagram author—for a rich, spacious conversation on Enneagram Type Five from the inside out.

Saleh shares how he discovered the Enneagram on a meditation retreat in 2017, why a spiritual frame matters to him, and how storytelling, metaphor, and nonverbal language can sometimes reveal a type more accurately than intellectual description. Kristin and Saleh explore the Five’s relationship to “knowing”—not as trivia-collecting, but as a visceral hunger to uncover what’s underneath things—and the challenge of trying to isolate “type” from other parts of personality (including cognitive styles and tritype dynamics).

From there, the conversation moves into the heart of Saleh's work and his book The Nine Barriers to the Heart: the way each type loses contact with essential qualities, chases a partial truth, and eventually discovers that the deepest change isn’t self-improvement—it’s acceptance. Together they name what Fives often avoid (emptiness), how that emptiness can feel like an existential threat, and why non-attachment isn’t an idealized spiritual pose but the byproduct of learning to be with what you’ve been running from.

Along the way, you’ll hear striking distinctions—Five “isolation” versus Four “estrangement,” how withdrawal can look polite on the outside while fear hides underneath, and why the quest for happiness can become its own mirage when it’s driven by the “miserable self.” If you’re a Five, love a Five, or want a more honest conversation about spiritual work that doesn’t bypass suffering, this one lands deep.

Russ Hudson | Part II Jan 08, 2026

Show notes

Jeff and TJ continue their conversation with Russ Hudson by pressing into the lived difference between low-side stress and the “secret ingredient” hidden inside our inner lines—what we avoid is often what we need. Russ unpacks how the Levels of Development change everything: when we slide down the “thermometer,” our stress point can feel like self-abandonment; but when we move with awareness, the same line can become medicine—an entry into shadow, wholeness, and a fuller human life.

From there, Russ introduces “shunting”—the way overwhelm can push us to camp out at a stress point to stop a deeper collapse—and reframes the inner lines as adaptive, liberating pathways rather than personality trivia. The conversation turns toward the three centers(head, heart, body), why “getting more of a center” isn’t about doing more thinking or more action, and why presence isn’t a mood—it’s the capacity to be awake to whatever is true.

They also tackle a live tension in the modern Enneagram world: pushback against “prescribing health,” the difference between information and transformation, and why real development takes time, experience, and patience. Russ shares wisdom on when people (especially teenagers) may or may not be ready for Enneagram work, why he no longer tells people their type, and how presence keeps us from using the system to control ourselves—or others.

The episode closes with Russ previewing upcoming trainings (including instincts and a course on freedom), plus a heartfelt exchange on what mature Enneagram teaching looks like: humility, openness, and a lifelong willingness to keep learning.

Learn more about Russ’s work and upcoming courses: russhudson.com

"Early Access" | Enneagram 2 | BJ in Texas Jan 07, 2026

Show notes

Katie talks to BJ about 2ness! We discuss why being a male 2 can make you feel different from your friends, the deep wish to be invited into someone's life, and how pride can worm its way into a 2's life without warning.

Find BJ on Instagram at @monty_queso

Find BJ on Blue Sky at @montyqueso.bsky.social

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