Around the Circle | An Enneagram Podcast

Latest Episodes:

Kristin Messegee | "Inside Story" Oct 16, 2025

Show notes

Jeff and TJ sit down with Kristin Messegee—an Enneagram Six coach and the host of Life Uninhibited—to announce her new narrative-style show, "Inside Story" joining the ATC family of podcasts.

We talk why real growth needs empathy, why stories teach better than diagrams, and how narrative Enneagram work helps us become emotional adults.

• Subscribe to Kristin's new Podcast : HERE

• Follow Kristin’s work: Coaching + Life Uninhibited – The Enneagram 6 Podcast. kristinmessegee.com+2kristinmessegee.com+2

• And if you want to get connected our best work, do sign up for a membership on Patreon .

Early Access | Enneagram 8 | Meaghan in Portland Oct 14, 2025

Show notes

Early Access on iTunes: HERE

Early Access on Spotify: HERE

Enneagram and Gender Discussion : HERE

Music is by GIANTS AND PILGRIMS

Katie's Work : HERE

Continuing her journey around the Enneagram, Katie talks to Meaghan, a freelance American Sign Language interpreter who loves traveling, new restaurants, and advocating for the deaf community.

We talk about the difference between anger and rage, how your childhood environment sticks with you, and get into some differences between 6 and 8.

Mistyping Twos | Part Two with Jackie Contessa Oct 13, 2025

Show notes

Jeff sits back down with Enneagram coach Jackie Contessa to walk through mistyping between twos and threes through nines.

If this helps, check the full Mistyping Chart Jackie co-authored in the back of our book Around the Circle . Or find Jackie at @tablefornineco and jackieccesa.com.

Generations | Boomer, Silent, Greatest with Tyler Zach Oct 09, 2025

Show notes

Link to the upcoming EnneaSummit : HERE

Link to all of our other work : HERE

Jeff sits down with Tyler Zach to preview his upcoming Midlife Summit (Oct 21–24). They dig into why “midlife has a branding problem,” the U-curve of happiness, and how the second half can move us from productivity to fruitfulness. Tyler shares tear-worthy moments from the panels (don’t miss the Sevens), why 60 is still “midlife,” and what happens when elders step into being elders—sages who lend hard-won wisdom across generations.

In this episode:

Midlife ≠ crisis: redefining the forties, fifties, and sixties as seasons of ascent
“Rehiring,” not retiring: purpose, reinvention, and new risks later in life
From skills to wisdom: becoming an elder instead of just getting older
Integrating the three centers with age—and why that brings real joy
Generational cycles (spring/summer/fall/winter) and what Gen Z can build next
Stories of resilience through illness, loss, and the long cocoon

About the Summit:

The Midlife Summit runs Oct 21–24 and streams free for four days (with optional lifetime access at an early-bird price). Panels feature respected voices from the Narrative tradition, the Enneagram Institute, Personality Hacker, and more. Grab the link in the show notes to register and see the full lineup.

Early Access with Katie Whitlock | Michael - Enneagram 7 Oct 07, 2025

Show notes

Early Access on iTunes: HERE

Early Access on Spotify: HERE

Music is by GIANTS AND PILGRIMS

Our inaugural Episode! In this discussion on Early Access, host Katie Whitlock sits down with her close friend Michael —an Ironman-in-training, soon-to-be husband, and a reluctant but curious student of the Enneagram.

Mistyping Twos | with Jackie Contessa Oct 06, 2025

Show notes

Enneagram Two gets a fresh look. Jeff sits down with coach and creator Jackie Contessa to unpack why “the Helper” label misses the mark and how that shortcut fuels mistyping. They trace the real motives at play—pride, flattery, intrusion, hidden grief, and the drive to “etch a role” in others’ lives—and name how gendered expectations distort typing (why many women lean Two and many men avoid it). Jeff and Jackie contrast Twos with Ones: duty and betterment vs. relational payoff, resentment from suppressed anger vs. resentment from unmet exchanges. They also hit possessiveness, boundaries as relationship-keepers, external energy vs. inner world, and the Two-to-Eight stress move. If you’ve ever wondered, “Am I a Two—or just helpful?” this one gives you a sharper lens.

Gen Z Oct 01, 2025

Show notes

Like the Enneagram, our Generation--its technologies and events--shape how we see the world.

In this conversation with Katie Whitlock, we will be exploring the values and cultural markers of Gen X, Millennials, and Gen Z, weaving together films, music, shared culture, and the defining experiences that mark each era.

Connect with us at www.aroundthecircle.org

Mistyping | Ben From L.A. | 8 or 1 Sep 29, 2025

Show notes

Get connect to all our work at www.aroundthecircle.org

In this episode, Jeff sits down with counselor Ben from Los Angeles for a live Enneagram mistyping session—could he be a principled One, a justice-driven Eight, or an analytical Five?

From his early years in LA to a career in corrections and counseling, Ben shares stories of resilience, accountability, and the ongoing work of channeling anger into growth.

Along the way, we highlight how Ones and Eights approach clarity, control, and problem-solving differently, giving listeners a front-row seat to the art of discerning type through real conversation.

Millennials Sep 24, 2025

Show notes

Like the Enneagram, our Generation--its technologies and events--shape how we see the world.

Connect with us at www.aroundthecircle.org

Mistyping | Sandy from Chicago | 4, 5 or 9 Sep 15, 2025

Show notes

See all of our best material at: aroundthecircle.org !

In this Mistyping session, Sandy from Chicago—a leadership and development coach—traces how infertility,and a bruising conservatory experience pushed her from “just tell me what to do” health coaching into deeper inner work. We talk holding space for grief without “positivity bullying,” growing up Midwestern “everything’s fine,” motorcycles as moving meditation, the love–hate of French horn performance, and learning to listen to her body. Then we press into typing: the pull between Five and Nine (with Four in the wings), what it means to prefer clarity over calm, intrusion over conflict, conserving energy, and hearing the heart-message that “your needs aren’t a problem.” Along the way: birding, butterflies, boundaries, and finding a voice that can move to Eight when needed. Connect with Sandy: swansoncoaching.com.

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