Typology

There's a particular kind of loneliness that comes from caring about something before anyone else in the room does. My guest today knows that loneliness intimately.
Rev. Dr. Derwin L. Gray played in the NFL before founding Transformation Church in 2010. He's also an Enneagram Eight — and in this conversation, we get into what it actually feels like to live inside that number: the passion that gets mistaken for anger, the instinct to protect people before they've asked to be protected, and the particular ache of caring more than the room does.
We explore the difference between using pain as fuel and actually healing it, because as he puts it, vengeance has a way of burning you up on its way out. He walks us through the HEAL framework from his new book, It's Time to Heal: Four God-Given Steps to Restore What Life Has Shattered and names his own core wound in three words I haven't stopped thinking about since we recorded.
If you've ever confused surviving a wound with healing it, this episode's for you.

What happens when a Three stops performing and starts telling the truth, even to herself?
Anthony and I sat down with Stephanie Barron Hall, author of Enneagram in Real Life and host of the Enneagram in Real Life podcast, for a conversation that starts with instinctual stacking and ends up somewhere much deeper. Steph, a sexual (or what she calls a "spark") dominant Three, unpacks how the sexual instinct differs from the social Three most people picture, why she was so often mistaken for a Four, and how she's learned to notice the exact moment she starts performing instead of being present.
We move through the difference between achieving your identity and receiving it, the religious trauma that shaped Steph's relationship to spirituality, and why she's going back to school in her late thirties to become a therapist. We also talk honestly about what it actually costs to tell yourself the truth, not just other people.
Steph is the author of Enneagram in Real Life, available wherever books are sold. Find her at ninetypes.co and on her own podcast, Enneagram in Real Life.
 
ABOUT STEPHANIE BARRON HALL
Stephanie Barron Hall (M.A. Organizational Communication & Leadership) is an Accredited Enneagram Practitioner, author of The Enneagram in Love (2020) and Enneagram in Real Life (2025), creator of @NineTypesCo, and host of the Enneagram in Real Life podcast. Stephanie has been facilitating personality-centric team development for years as an outside consultant for organizations ranging from small businesses to Fortune 100 companies. Stephanie's approach to the Enneagram is grounded in communication theory and emphasizes deep personal work through application, curiosity, and self-awareness.

Dr. Alison Cook, bestselling author of Boundaries for Your Soul, returns to Typology to talk about her new book, The Secure Soul: Finding Inner Strength and Connection When Trust Doesn't Come Easy. Alison is candid about her own lifelong wrestle with insecurity as an Enneagram Three, and we dig into two of her book's central characters: the controller, the part of us trying to earn love by managing how we're perceived, and the shadow, the part left holding everything we couldn't afford to feel. Drawing on Internal Family Systems, attachment theory, and contemplative Christian tradition, Alison offers a different way to think about the soul — not as a machine to fix, but as a mountain to explore, one shadowy valley at a time. Along the way: Gabor Maté's idea that children are forced to choose between attachment and authenticity, why "I am loved even here" might be the whole gospel in five words, and the real difference between fixing yourself and healing.
 
About Dr. Alison Cook: 
Dr. Alison Cook is a psychologist of religion, licensed therapist, and host of the top-ranked The Best of You Podcast. She is the author of several bestselling books, including Boundaries for Your Soul. Known for her work at the intersection of faith, psychology, and spiritual formation, she helps people cultivate a secure inner life– healing past wounds, strengthening a grounded sense of self, building healthy relationships, and experiencing God as a steady and loving presence in their lives. She and her husband, Joe, are the parents of two adult children and call the mountains of Wyoming home.
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What happens when the type you've claimed for years turns out to be wrong? Today, I sit down with returning guest Beatrice Chestnut — Enneagram teacher, author, and co-founder of the Chestnut Paes Enneagram Academy — for a wide-ranging conversation on one of the most common (and most human) struggles in Enneagram work: mistyping.
We dig into why mistyping happens, how to hold a hypothesis about someone's type without imposing it, and the subtype distinctions that resolve the Enneagram's trickiest lookalikes — especially Twos vs. Nines and the three very different faces of Type Four and Type Six. Beatrice also opens up about her own evolving growth path, and I share a personal story about the moment a single sentence in one of Beatrice's books changed how I understood myself.
IN THIS EPISODE
Why mistyping is a normal part of the self-discovery journey — not a system failure
How to gently raise a hypothesis about someone's type without playing "Enneagram police"
The key differences between Twos and Nines (emotional expression, image-consciousness, who initiates)
Self-preservation, social, and sexual subtypes of Type Four — the "glad," "sad," and "mad" Fours
Why Sixes so often don't recognize their own fear-based motivation until they find the Enneagram
Beatrice's personal reflection on growing from a Four toward Eight-like strength
What it actually feels like when your type finally "lands"
ABOUT OUR GUEST
Beatrice Chestnut, PhD, is the co-founder of the Chestnut Paes Enneagram Academy and author of The Complete Enneagram (new edition available next month) and The 9 Types of Leadership. Learn more at beatricechestnut.com.

True spiritual transformation often begins at the exact moment our old answers stop working.
This week, I'm sharing Chapter One of my newly revised novel, Chasing Francis: A Pilgrim's Tale. We follow Chase Falson, a megachurch pastor whose public confession of lost faith triggers an unexpected journey of the heart. While Chase's story is fictional, his hunger for something authentic mirrors my own season of wrestling with sterile religion. By sending Chase to Assisi to walk in the footsteps of St. Francis, I discovered that losing an inherited belief system isn't the end of faith—it's often the doorway into a far deeper, living encounter with God.
Whether you haven't set foot in a church in a decade or you're sitting in a pew this Sunday, this episode is for anyone who's ever quietly wondered if there's something more.
 
Resources & Links: 
Book: Pick up your copy of Chasing Francis: A Pilgrim's Tale
Audio: Listen on Audible or wherever you listen to audiobooks
Connect: Follow the show and connect with Ian on social at @ianmorgancron