Show Notes
This Christmas, we're delighted to bring back one of our most beloved conversations with Enneagram Three, pastor, and author AJ Sherrill. In this replay, AJ joins me to revisit the Nativity story—not as the sentimental tale we often breeze past each year, but as a rich, multilayered narrative pulsing with mystery, courage, vulnerability, and divine surprise. AJ shares his own journey into spiritual direction, what it's teaching him about listening, presence, and compassion, and how the Enneagram continues to shape his inner world. We explore why the season invites us to slow down, pay attention, and resist the frantic pace that so easily numbs our capacity for wonder. Together, we dig beneath the familiar Christmas imagery to uncover the often-misunderstood characters who surround the manger—the homeowner who offered radical hospitality, Zechariah rediscovering awe through silence, and even Herod, whose shadow side has more to teach us than we might expect. Their stories echo our own desires, fears, and growth edges in striking ways. We also have some fun speculating about the Enneagram archetypes present in the Christmas narrative—Mary, Joseph, John the Baptist, and others—and how their unique postures toward God can inspire our own transformation. This episode is thoughtful, illuminating, and sprinkled with the kind of laughter and honesty that always seems to show up when AJ is with us. A perfect listen for Christmas Day. Settle in, take a breath, and join us as we rediscover the story beneath the story—and the God who meets us there.
More from Typology
Wm. Paul Young returns to Typology for a wide-ranging conversation about forgiveness, redemption, regret, grief, and hope. Paul shares what he's learned from his friendships with men on death row, the surprising story of how he came to release expectations of his father, and why forgiveness and reconciliation aren't the same thing. We also talk about forgiving ourselves, having "sorrow days," staying present instead of future-tripping, and the redemptive ways God can meet us in the middle of our biggest mistakes. Plus, Paul shares the story behind The Return of the Shack, his long-awaited continuation of the story that began with The Shack.
This week I sat down with Drs. Les and Leslie Parrott, an Enneagram Eight and Two who have been married for more than forty years, for a fun and personal conversation about love, mental health, and self-awareness. We talked honestly about what it actually takes to stay curious, connected, and growing in our relationships. And, we explored the ways our best qualities can sometimes get distorted, what anxiety can teach us about ourselves, and why self-awareness is often the beginning of real change. I noticed that nearly every story we shared came back to the same thing. Les has a phrase for it: awareness is curative. He talked about the anxiety he's carried since he was young, and how simply naming it "is like putting a handle on a hot tea kettle; suddenly you can pick it up." Leslie spoke with tenderness about the seasons of her life where she has struggled and her long road back. Their experiences are why they wrote their new book, The One Year Positive Mental Health Devotional (Tyndale, October 6, 2026). With society leaning into the mental health crisis, especially among young people, Les and Leslie felt it in their personal lives and daily work and wanted to provide a companion for all of us holding it together on the outside while something unravels underneath. It's an invitation to recognize and sit with where you really are. At the same time, their MyHeartChart quiz grows from the same root. While the Enneagram describes who you are, your traits, your wiring, MyHeartChart tells you where you are right now in the relationship that matters most to you. It's an opportunity to take the pulse of the state of your relationship, alone…for free. This is a conversation about marriage, parenting, mental health, the Enneagram, and the ongoing work of becoming more present to the people we love. But more than anything, it's about learning to notice ourselves so we can show up differently for each other.
What if intimacy with another person begins with learning how to be intimate with yourself? Ian talks with Enneagram teacher and transformational coach Suzanne Dion, co-author with the late Dr. David Daniels of The Enneagram: Relationships and Intimacy, about vulnerability, self-acceptance, defense mechanisms, and the ways our personality patterns can keep us disconnected from ourselves and the people we love. Suzanne introduces David Daniels' Five A's of the Universal Growth Process—awareness, acceptance, appreciation, right action, and adherence—and explains how this practice can help us stay present when we're confronted with fear, shame, mistakes, and the painful gap between who we are and who we think we're supposed to be. It's a conversation about the undefended heart, the courage to be known, and what it means to cultivate a more spacious, magnanimous presence in our relationships.
What if you had learned the Enneagram when you were a teenager? In this replay of my conversation with Ainsley Britton, author of The Enneagram for Teens, we explore what self-awareness can look like during adolescence and how parents can use the Enneagram without turning it into another way of labeling or controlling their kids. Ainsley and I talk about why she believes teenagers can benefit from learning the Enneagram, why it should be held loosely, and why parents should never force it on a teenager who isn't interested. We also discuss parenting, curiosity, vulnerability, mental health, relationships, and one of the most important things we can remember about the Enneagram: We are more than our numbers. In this episode: The significance of the Enneagram for teens and its potential to aid in self-discovery. The challenges and joys of being an Enneagram Type 2. Practical advice for parents on introducing the Enneagram to their children without forcing it. The role of mental health awareness in today's youth and how the Enneagram can facilitate important conversations. Whether you're a parent, educator, or simply curious about the Enneagram, this episode is packed with insights and laughter that you won't want to miss! *This episode is a replay of an earlier conversation with Ainsley.
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.