Around the Circle | An Enneagram Channel

In this installment on the Enneagram’s processing centers, Jeff Cook and Katie Whitlock engage When Working Together Doesn’t Work by Joey Schewee, focusing on the doing center through Types One and Three.The conversation explores how these types assess life through action—how progress, productivity, and accomplishment become the primary lens for determining whether things are working.For Ones and Threes, doing is not secondary; it is the ground of evaluation, the place where identity and meaning begin to take shape.

What can joy survive?In this conversation, Jeff Cook sits down with licensed trauma therapist and author KJ Ramsey to explore the surprising relationship between pain, joy, identity, and healing.Drawing from her upcoming memoir The Place Between Our Pain, KJ shares how chronic illness, trauma, and the limits of control reshape our understanding of time, self, and what it means to be held. Together, Jeff and KJ examine the tension between despair and hope, the role of the Enneagram in personal growth, and the deep question beneath it all:Can joy still exist when everything falls apart?This episode moves through themes of:Trauma and post-traumatic growthThe “true self” vs. personalityChronic illness and the experience of timeJoy as presence, not performanceAgency, embodiment, and survivalFaith, meaning, and the limits of understandingWhether you're navigating suffering, exploring the Enneagram, or asking deeper philosophical questions about identity and purpose—this conversation offers both honesty and hope.📘 KJ Ramsey’s BookThe Place Between Our Pain: A Memoir of What Joy Can Survive→ Pre-order & learn more: https://www.kjramsey.com🌐 KJ Ramsey Website→ https://www.kjramsey.com🎙️ Around the CircleThe Enneagram publishing platform: Podcast • Books • Video • Ongoing formation→ Join the community: https://www.aroundthecircle.org→ Become a member: https://www.patreon.com/aroundthecircle📅 Live Event (Colorado)KJ Ramsey + Suzanne Stabile → April 17–18 : HERE

What does it feel like to move through life believing your presence doesn’t quite matter?In this episode of Early Access, Katie Whitlock talks with Blake Walker, an Enneagram Nine, about the quiet patterns that shape her life—from avoiding conflict to merging with others’ goals, to the slow realization that her own voice matters.Blake reflects on marriage, motherhood, and building a life that at times felt more aligned with others than herself. Along the way, they explore the Nine’s relationship to energy, anger, and purpose—revealing both the strength and struggle of a type that longs for peace but often loses itself in the process.

As we close out Season One of Inside Story, Kristin Messegee and Jeff Cook reflect on what they’ve learned—and where the Enneagram needs to go next.This conversation moves beyond theory into practice. What actually changes us? Why do we avoid our core emotions—anger, shame, and fear—and what does it take to face them? Across the triads, patterns emerge: image types struggle to access shame, body types resist seeing their impact, and head types find subtle ways to avoid anxiety altogether.

We’re back for Part Two of our deep dive into Personality and Wholeness in Therapy—and this time, we step into Chapter One.In this episode, we explore three core ideas shaping Dr. Siegel's model. We trace how early temperament forms a kind of filter, how neural pathways reinforce our patterns over time, and why growth is less about changing your type and more about loosening its grip. We also examine Siegel’s integration model—one that calls us not into a different type, but into balance across the centers.We are gathering on Tuesdays to discuss. The sign up is : HERE

Explore more of Around the Circle, join live discussions, and access exclusive content: HERE___________We’re back in —and diving deeper into Joey Stabile’s Working Together Doesn’t Work, focusing on the Processing Center and what it reveals about how different types move through the world.In this episode, we begin a discussion on Eights, Threes, and Ones—the “doing processors.” What does it mean to process through action? What gets gained—and what gets left behind—when execution becomes the primary lens for evaluating life?We explore Joey’s framework of support centers—how doing can be backed by thinking or feeling—and how that shapes the differences between types that, on the surface, look similar. Along the way, we unpack:Why Eights often feel misunderstood—and what’s actually happening beneath their intensityThe tension between execution and emotion in doing typesHow Threes, Eights, and Ones differ in their relationship to results, relationships, and responsibilityWhether the “ends justify the means”—and how each type defines both ends and means differentlyThe hidden cost of prioritizing action over reflection or connectionThis conversation slows down to wrestle with real language, real experience, and the deeper structure behind how we assess: Am I good in the world?We’ll pick up next time with Threes and Ones—but for now, we stay with the Eights, and what it means to move through life with force, clarity, and blind spots we don’t always see.

The beginning of the end! In this episode, Katie talks with Luke, a pastry chef turned mental health counselor.We talk about several differences between 3 and 9, and spend a lot of time diving into what it means for a 9 to "wake up" and start chasing after their own life.Luke has an incredible knack for explaining difficult concepts, so this is a good one to listen to if you want to understand the 9s in your life.

What are we really talking about when we talk about the Enneagram?In this Morning Show conversation, we move past surface-level typing and into something deeper—transformation, self-awareness, and the courage to face what’s actually being exposed in us.We explore:Why the Enneagram is more than insight—it’s a tool for real-time self-awarenessThe difference between knowing your patterns and interrupting themHow unconscious motivations shape our lives (and how to bring them into the light)Why “what do I want?” might be one of the most powerful questions you can askThe tension between shared human flourishing and personal transformationHow each type filters reality—and what that means for relationships, emotions, and growthAlong the way, we engage ideas from Carl Jung, Brené Brown, and Dr. Daniel Siegel’s Personality and Wholeness in Therapy, while also diving into the practical, lived experience of using the Enneagram.

In this episode, we dive into Joey Schewee’s new book "When Working together Doesn't Work" -- Which you can buy: HERE.We introduce a framework reshaping how we are understand the Enneagram. What begins as a familiar observation—types orienting around accomplishment, connection, or ease—becomes something far more grounded as we explore the underlying mechanism that produces these patterns.Rather than stopping at outcomes, Joey’s work traces how each type processes experience from the inside out, offering a clearer structure for why we assess our lives the way we do. This conversation moves beyond description into explanation, giving language and form to something many have sensed but not fully articulated.

We’re launching something new inside Around the Circle: The Reading Room.Take a listen. We will be discussing the book by Dr. Siegel starting Tuesday, March 24th, 2026. Sign up for : HERE___In this episode, Jeff begins a chapter-by-chapter deep dive into our first book: Personality and Wholeness in Therapy.Written by a team of PhDs and medical doctors and led by Dr. Daniel J. Siegel (Harvard-trained, UCLA professor of psychiatry), this book represents a major shift. It takes the Enneagram out of the realm of “wisdom tradition” and places it in conversation with neuroscience, developmental theory, and clinical practice—drawing on over 50,000 narrative interviews.We will post episodes of this sort weekly, and they will serve to set up our Tuesday night conversations. Our First Live Session will be Tuesday, March 24, 2026Join us by:Getting the bookReading the introductionSigning up at aroundthecircle.org for $20 membershipThink of this as a gym membership—but for your inner life.We’re building a space not just for content, but for conversation, clarity, and growth.If you’ve wanted a place to think out loud about the Enneagram with others who take it seriously—this is it.

Katie talks with her new friend Grace in this episode! Grace is an Enneagram coach based in Dallas, Texas. We discuss the core motivation of 8s (and how it shows up in Grace's daily life), an 8's hesitancy to discover their own limitations, and the similarities/differences between 8s and a few other key numbers.Find Grace on Instagram hereCheck out her website here

Episode Two of the Morning Show and we are joined by the TJ Wilson.We are talking about the art of advice. Together they explore why giving advice can feel so natural, why receiving it can feel so difficult, and how often “help” is tangled up with control, fear, projection, or the need to be affirmed.The conversation moves beyond simple tips and asks a bigger question:When we seek guidance, are we really asking what to do next—or who we are becoming?They also discuss:the difference between advice, coaching, and therapywhy many people asking for advice may actually want approvalhow each Enneagram type can be compelled to offer help in different waysthe role of curiosity, respect, and autonomy in healthy supportwhy growth often begins beneath the surface problemwhether coaches should have a universal target for health and flourishingThis is a rich, funny, and surprisingly deep conversation about wisdom, self-awareness, and the kinds of questions that actually help people change.

Our monthly Second Saturday gathering continues as we explore the high side of the Enneagram through conversation, reflection, and lived experience. This is our recording from last month.Do join us March 14th. Become a member of aroundthecircle.org and go HERE to sign up.___In this session, we focused on Twos and Threes—looking closely at the fears, patterns, and excesses that can pull these heart types off center, and the deeper messages that begin to move them toward freedom. Together, we explored how Twos relate to need, care, pride, and control, and how Threes wrestle with validation, achievement, image, and the longing to know their worth apart from performance.What made this conversation especially rich was the honesty in the room. Participants shared stories about relational risk, self-love, grief, retirement, emotional presence, and the challenge of letting go of the need to manage how others feel or how they see us. We also reflected on the heart’s message, the holy ideas, and the virtues that begin to emerge when these types loosen their grip on old survival strategies.This gathering is part teaching, part discussion, and part crowdsourcing—an opportunity to listen deeply to one another and to consider what real movement toward wholeness looks like from the inside out.In this conversation:the “45-pound weight” each type carries through fear and fixationwhy Twos struggle to name and honor their own needshow pride, control, and the longing for reciprocation show up in Twoswhy Threes often tether worth to achievement and validationhow grief, stopping, and emotional honesty become part of healing for Threesthe role of the heart’s message, holy ideas, and virtues in moving toward the high side of typeWe’ll gather again on March 14 as we continue the conversation with Fours and Fives.

Katie sits down with Emma, a 35-year-old Enneagram Six, for a thoughtful and personal conversation about fear, preparedness, relationships, and the long road toward self-trust.Emma shares how she first found the Enneagram through podcasts, what it was like to recognize herself as a Six, and how that discovery helped make sense of patterns she had carried for years. Together, Katie and Emma explore the inner world of Sixes: the search for safety, the struggle to trust themselves, the experience of rumination, and the deep need to find what feels “just right.”They also talk about Emma’s relationship with her boyfriend, an Enneagram Three, the differences between Six and Three achievement, and how the Enneagram helps illuminate the push and pull of connection. Along the way, Emma reflects on growing up between cultures, including her childhood in Saudi Arabia, and shares how an early medical emergency became one of the defining moments in her relationship to preparedness and control.

So … what does it mean to be happy anyway?!In this episode of The Morning Show, Jeff is joined by Enneagram teachers Jackie Contessa and Kristin Messegee to explore the relationship between the Enneagram and happiness.Together they consider whether happiness is something we pursue, something we cultivate, or something that emerges when we begin to see through the patterns of personality.Along the way we explore ideas like enjoyment, satisfaction, meaning, purpose, and the sense of a life well lived.The conversation also explores:• how different Enneagram types might approach happiness differently• the role of struggle, maturity, and personal development• whether happiness can coexist with grief or hardship• how relationships shape our experience of happiness• why growth may require surrendering older versions of ourselvesIf the Enneagram is a map, this episode asks a deeper question: where is that map actually trying to lead us?

Jeff sits down with therapist Lindsay Taylor of Hope Springs Counseling in Alabama for a wide-ranging, honest conversation about the inner world of Enneagram Ones—especially what it takes to stay grounded when everything feels like it’s on fire. Together, they explore the One’s visceral experience of brokenness, the exhausting question of “what is mine to do,” and why the Serenity Prayer keeps showing up as a lifeline.Along the way they unpack autonomy, boundaries, grief disguised as anger, the temptation to escape into “future-fixing”, and why past-work can feel both threatening and essential—less about reliving pain and more about gaining compassion, clarity, and a fuller relationship to time (past, present, and future).You can connect with Lindsay at : www.HopeSpringsCounseling.net

Y’all, this one is REALLY GOOD. In the first half we talk typical 6 stuff: counter phobic vs phobic, reading other people’s emotions, etc. But in the second half, we get into some new stuff and it’s one of my favorite episodes to date.There are a few seconds of audio issues around the 47 minute mark (we had some technical problems during recording), but hopefully you all can still understand!Find Hunter Mobley’s book here

In this exchange, Kristin and Joey explore how differently the types move through the world—especially around communication, authority, affirmation, and intensity. They also examine crisis strengths, autonomy, vulnerability, and the common mistyping of bold people.The discussion broadens into themes of parenting, growth, and self-awareness. Joey reflects on raising children with an understanding of stance and wiring, while Kristin speaks candidly about discovering her own fear and authority patterns later in life. Together, they emphasize that the Enneagram doesn’t change hardwiring—but it can transform how we relate, how we repair, and how we take responsibility for the impact we have on others.LinksInside Story episode (Apple): HEREKristin Messegee's Coaching: HEREAll Joey Schewee's work at WE Solutions: HEREJoey's Upcoming book: "When Working Together Doesn't Work" : HERE

Jeff sits down with grief expert and Enneagram guide Mandy Capehart to unpack what national grief really feels like — not just personal sorrow, but the deep cultural distress many Americans carry today. Together they explore the emotional impact of polarized culture, lost shared reality, and fear-driven responses in our relationships and communities. Mandy offers insight into how regulation, one-on-one connection, and lived values can help us navigate overwhelm and reclaim humanity in a fractured world. If you’ve felt disillusioned, scared, or unsure how to engage with big problems without burning out, this episode invites you into deeper awareness, compassionate action, and hope rooted in connection — not just outrage.About Mandy & Where to Listen:This episode features Restorative Grief with Mandy Capehart – Podcast Page, a show that explores grief in all its forms — from loss of loved ones to life transitions, identity shifts, and the heartbreak of unsolved cultural pain. 👉 Listen to Restorative Grief on Apple Podcasts, Spotify, or your favorite player for compassionate stories and practical tools for navigating grief and growth. Connect with Mandy:Website: mandycapehart.comInstagram: @mandycapehart

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 : HEREPick 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 guide born from 17 years of consulting and leading teams—and then Kristen pivots into the heart of the episode: Eight confidence, intensity, and the misunderstood inner world beneath the “big presence.” Joey challenges common stereotypes (and mistypes), reframes Eight “reactivity” as fast-moving anger that clears quickly, and names the real fuel behind Eight conflict: injustice, low effort, and compromised integrity.Together they explore the push-pull between autonomy and connection, why Eights often feel uncomfortable when attention turns toward them, and how “wanting” energy from others can feel intrusive—especially when it isn’t grounded in authenticity. Joey also shares what changed after facing something she couldn’t control, how anger can cover tenderness, and why gut types may be the most intuitive in the system.Again, Joey’s book When Working Together Doesn’t Work is available for pre-order now on Amazon and releases in March, and you can get it : HERE .

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)

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.

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.

This is our Second Saturday Workshop from January!Members can sign up for all of our coming workshops : HEREIn 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 : HEREOn 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.

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 ofthoughtandfeelingFind Lucas' music on Spotify