From the NFL to the Pulpit: Derwin Gray on Forgiveness, Fear, and Finding Your Father

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. Facebook  Instagram Website The Best of You Podcast    

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  

Most Enneagram teaching is very good at describing what's wrong with you. This episode is about what's right. Every Enneagram type has a Passion — the chief emotional distortion the ego runs when it's disconnected from its truest self. Anger for the One. Pride for the Two. Deceit for the Three. Each of the nine types has one, and most of us have spent a lot of energy trying to manage ours without quite knowing what it is. But every type also has a Virtue. Not a moral achievement you add on top — a quality that naturally arises in the heart when the Passion loosens its grip. Serenity. Humility. Authenticity. Equanimity. Non-Attachment. Courage. Sobriety. Innocence. Right Action. These aren't things you build. They're things that emerge when you stop being in the way of yourself. In this final episode of the Enneagram Essentials series, Anthony and I walk through all nine Passions and their corresponding Virtues. I share what Equanimity feels like in my own life as a Four — when I manage to access it — and we close with two honest answers to the question of how any of this actually becomes real: contemplative practice, and a particular kind of willingness to stop running from pain. This is a hopeful episode. Everything in the series has been building toward this. The Enneagram has always been pointing here.   This is Episode 5 of 5 in the Enneagram Essentials series. All five episodes are available now wherever you listen to Typology.   RESOURCES FROM THIS EPISODE:  The Road Back to You by Ian Morgan Cron  The Story of You by Ian Morgan Cron Enneagram Assessment | Find Your Type Ian's speaking and organizational work   Follow Ian on Instagram | Facebook | TikTok | YouTube 

When you combine an Enneagram type with a dominant instinct, you get a subtype — and there are 27 of them. This is the level at which most people finally, fully recognize themselves in the Enneagram. Not at the type level, not at the instinct level, but here — where the two come together into something precise enough to actually fit. In this episode, Anthony and I walk through what subtypes are, why they matter so much, and what some of the most striking examples look like in practice. We spend time on the counter-phobic Sexual Six, who presents so differently from the general Six description that mistyping as an Eight is extremely common. We look at the Self-Preservation Four — stoic, tough, nothing like the image most people carry of the Romantic type — and the Social Three, whose image management has become so sophisticated that they can appear humble and self-effacing while running every calculation in the room. We also talk through how to identify your own subtype, what Beatrice Chestnut's work has contributed to this area of teaching, and what to do with the discomfort that often arises when a subtype description lands a little too accurately. If you've ever felt like your type description is about right but something important is still missing — or if you've ever thought you might be two different types — this episode is the one that usually resolves it.   This episode builds on Episode 3 (Instincts). Listen to that one first if you haven't.     RESOURCES FROM THIS EPISODE: The Complete Enneagram: 27 Paths to Greater Self-Knowledge by Beatrice Chestnut  The Road Back to You by Ian Morgan Cron The Story of You by Ian Morgan Cron Enneagram Assessment | Find Your Type Ian's speaking and organizational work    Follow on Instagram | Facebook | TikTok | YouTube

Here's something I've noticed after years of teaching the Enneagram: there's usually a moment when someone who knows their type well suddenly encounters something that doesn't fit. A behavior they can't explain. A pattern that seems to contradict everything their type is supposed to do. More often than not, the answer lives in the instincts. In this episode — Episode 3 of our Enneagram Essentials series — Anthony and I go into one of the most undertaught concepts in popular Enneagram culture: the three instinctual drives. Every human being is wired with three biological survival drives — Self-Preservation, Social, and Sexual (or One-to-One). These aren't psychological preferences. They're primal. They predate the ego. And they operate in a hierarchy — which means that depending on which instinct fires first for you, two people of the same Enneagram type can look almost nothing alike. We walk through all three instincts in detail: what each is oriented toward, what it looks like in everyday life, what its shadow side is, and how to start identifying which one is dominant for you. We also talk about the Repressed instinct — the drive that tends to be most underdeveloped — and why understanding it can explain a remarkable amount of friction in your closest relationships. If you've ever felt like your type description is about 80% accurate and you can't figure out what the other 20% is — take a deeper look at instincts.   **This episode is part of the Enneagram Essentials series. Episode 4 builds directly on today's content, so listen in order if you can.  

Most people who know the Enneagram know their type. Fewer know their Basic Fear. And even fewer have sat with it long enough to understand why knowing your basic fear is so important. In this episode — the second in our Enneagram Essentials series — Anthony and I go beneath the type descriptions and into the motivational core of the system: the nine Basic Fears and their counterparts, the nine Basic Desires. These are the engine underneath every pattern the Enneagram describes.  We go through all nine — what each type is running from, what it's running toward, and what it actually looks like when that fear is in the driver's seat. I also share something personal about what the fear of being ordinary has looked like in my own life as a Four. And we close with a practical practice you can start this week — one that will tell you more about your type than most assessments will. If you've been wondering why the Enneagram sometimes feels like it's describing your behavior but not quite explaining it, this is the episode. The explanation lives here. **This episode is part of the Enneagram Essentials series. Start with Episode 1 if you're new — it's a listener mailbag covering the basics and framing the series.       For additional Enneagram resources, visit https://IanMorganCron.com To register for the Enneagram Ones webinar, "Learning to Let Go," visit https://ianmorgancron.com/lettinggo

After nine seasons of Typology, Anthony and I thought we should revisit some of the basics.  This is the first episode of a five-part series we're calling Enneagram Essentials. Think of today as the front door — we cover the ground every listener needs, from how to find your type to how the Enneagram works in relationships, in faith, and in seasons of genuine suffering.  Then, in Episodes 2 through 5, we go deeper into the concepts that most Enneagram teaching glosses over: Basic Fears and Desires, Instincts, Subtypes, and Virtues. The four things that, in my experience, change everything once you actually understand them. Whether you found the Enneagram last week or you've been sitting with it for years, there's something in today's conversation for you.