Around the Circle | An Enneagram Podcast

Another wonderful conversation with Brenden from Ohio who is looking to verify his type.If you would like to purchase our book with the mistyping guide, it is HERE.To connect with us or to get your own mistyping interview, connect with us at: aroundthecircle.org

This is the first in our series on mistyping.We speak with Rachel from Minnesota as she reconsiders what she has always been told about her Enneagram Type.If you would like to purchase our book with the mistyping guide, it is HERE.If you are interested in doing a typing session with us, you can connect with us on Instagram: HERE. For all our other content go to : www.aroundthecircle.org

Co-Host of the Fathoms Podcast, Lindsey joins us to talk about her movement from thinking she was a Two to a Seven.Full version at www.aroundthecircle.org

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.

Link to the upcoming EnneaSummit : HERELink to all of our other work : HEREJeff 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 lifeFrom skills to wisdom: becoming an elder instead of just getting olderIntegrating the three centers with age—and why that brings real joyGenerational cycles (spring/summer/fall/winter) and what Gen Z can build nextStories of resilience through illness, loss, and the long cocoonAbout 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 on iTunes: HEREEarly Access on Spotify: HEREMusic is by GIANTS AND PILGRIMSOur 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.

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.

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

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.

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

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.

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. In this episode we tackle Gen X: from latchkey kids and divorce to the rise of the internet and shifting individualism, we ask what makes each generation unique, how those shifts impact personality and relationships, and why the Enneagram found fertile ground in Gen X’s world. Connect with us at www.aroundthecircle.org

Jeff sits down with Elliot, a Kiwi in London. They trace Elliot’s deconstruction and church life, his work building inclusive spaces, and how the Enneagram has helped him sort clarity from certainty.

Sexuality isn’t just behavior—it’s an internal experience. We sit down with researcher-coach Dr. Sam Greenberg to map how Enneagram type and instincts shape desire, cues, assertiveness, and intimacy. Sam outlines the gifts and challenges of each instinct, why instincts often predict sexual patterns more than type, how repressed instincts show up in the bedroom, and what happens in common pairings (like self-pres x sexual). We also hit evolutionary frames, honeymoon-phase myths, “service sex,” stress/context loads, and practical ways couples can reduce friction and increase connection—without shame.What you’ll learnA working definition of sexual desire vs. sexual behaviorWhy instincts set the framework and type adds nuanceGifts/challenges of self-pres, social, and sexual dominanceHow repressed instincts derail empathy, safety, or passionCommon pairing dynamics (self-pres × sexual, etc.) and best practicesWhy stress, sleep, money, and context change desire—and what to do about itConnect with our guestIG: @enneagasm (Sexy First Fridays with therapist Lindsay Frazier)Web: EnneagramSexpert.comAS always : all our best material is at : www.aroundthecircle.org

Tammy joins Jeff for a live mistyping session that moves from opera halls to IT dashboards—and into the deep stuff beneath type. A lifelong Michigander with three degrees, a choir section-leader, and a self-described “walking contradiction,” Tammy is blunt and kind, fiercely independent, and devoted to care (for people…and five cats). Together we explore comparison, authenticity, and the tension between being known and staying buttoned-up. 

Jeff had a stellar conversation with Enneagram Coach, Spiritual Director and Founder @reflecttheoriginal , Sarina Sherring.You can connect to her work here: www.reflecttheoriginal.auFor the full interview go to: aroundthecircle.org

This week we are joined by Amanda from Michigan. This was an excellent conversation!If you are interested in our mistyping guide : GO HEREThe guide is only in the print version.

This is a wonderful interview with the fantastic TJ Teems. Tj is a professional Enneagram Counselor in California. You can connect with her : HERESign up for a membership to all of our stuff : HERE

This one felt more difficult and we spent a lot of time looking not only at 1347, but you will hear a lot of questions for 2 and 6 as well. Jump in, tell us your thoughts on Spotify comments or on our website.__The mistyping guide is **EXCLUSIVELY** in the print version of the book. And can be found here: https://a.co/d/g7jBNnj

We continue our deep dive into Heroes in film, this time choosing to elevate a singular actor.If you are interested in seeing info about the Weld County Food Bank : GO HEREYou can connect with us and see all our best stuff at : aroundthecircle.org And check out Movie Typing : HERE