Around the Circle | An Enneagram Channel

In this episode, Katie talks with a local friend about all things 6. We discuss why some 6s might mistype as 4s or 8s, what rebellion looks like and why 6s do it, procrastination, and much more! Find Ava's interior design account here: https://www.instagram.com/rose_junction_/

Coaching for Enneagram Sixes with Kristin : HERE Pick up Joey Schewee's new book : HERE ___ On this episode of Inside Story, host Kristin Messegee sits down with Enneagram teacher and workplace consultant Joey Schewee for a candid, surprisingly personal conversation about what it’s actually like to live inside Type Eight. Joey opens with her upcoming book, When Working Together Doesn’t Work —a gui...

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...

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...

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...

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 Virt...

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

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...

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. J...

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, l...

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 E...

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 div...

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 inte...

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, ho...

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...

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 hum...

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.

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 ho...

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...

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

Our full catalogue of Rewired Episodes are at : www.aroundthecircle.org We land the plane on our stance series by wrestling with the language for Fours, Fives, and Nines.  Starting with Karen Horney’s “detached,” David Daniels’ “receptive/internalizing,” Suzanne Stabile’s “withdrawn,” and Joey Schewee’s “solitary,” they trace the history of stance, sift the pros and cons of each term, and ult...

On this episode of Scientific Enneagram , Danielle—engineer, Type 9, and endlessly curious mind—kicks off a foundational series by tracing the (surprisingly recent) history of psychology and asking a practical question: where does the Enneagram fit when we try to study people with scientific rigor? Starting with early introspection and its “observer problem,” Danielle walks through the major movem...

Russ Hudson joins Jeff Cook and TJ Wilson for a long-awaited conversation celebrating The Wisdom of the Enneagram—and, in particular, the “triads” framework that has shaped so much of modern Enneagram language and practice. Jeff calls the book a generational achievement and says (without exaggeration) that much of his own work has felt like “footnotes” to its conceptual architecture—especially Cha...

Continuing our journey through 1ness, Katie talks to Olivia this week. We discuss anxiety (and why it doesn’t always apply to all reactive types), trusting yourself, and what it means to experience true intuition. If you are interested in applying to be guest : GO HERE

Every Tuesday at www.aroundthecircle.org we release a "Rewired" episode for all members. This is an example of our most recent discussion on stance. In this Rewired episode, Jeff and Katie keep their stance series rolling and turn the spotlight on the “aggressive/assertive/independent” triad—Threes, Sevens, and Eights. They trace where the classic stance language came from Karen Horney, Riso &...