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...

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...

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...

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...

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 be...

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...

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...

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...

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 th...

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 natu...

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 diff...

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...

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 wha...

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...

There's a particular kind of courage it takes for a Nine to write a book called Good Boundaries and Goodbyes — and Lysa TerKeurst has earned every word of it. Join us as we revisit Ian's conversation with the New York Times bestselling author to explore what it actually looks like to wake up from the Nine's trance of self-forgetting, find your voice, and learn to hold the line with compassion and clarity.

Lysa gets honest about her own journey: the years of codependency during a long marriage marked by addiction and affairs, the discovery that boundaries aren't wa...

What does it mean to "get it right" as a parent?

Not perfectly. Not without regret. Not with some airtight system that guarantees your children will become exactly who you hoped they'd be. But with intention. With humility. With the long view in mind.

In this replay episode of Typology, I sit down with Andy and Sandra Stanley—both Enneagram Ones—to talk about their book, Parenting: Getting It Right. And what unfolds is a deeply honest, practical, and surprisingly tender conversation about parenting toward relationship instead of mere compliance.

Andy and Sandra shar...

We're going back into the vault for one of our most popular mailbag episodes from Season 3 — and the questions are just as good as we remembered.

In this episode, Ian and co-host Anthony Skinner answer listener questions on some of the Enneagram's most nuanced and personal territory: Can trauma actually change your type? What is the "sunny Four," and why do subtypes matter so much for Fours and Sixes? How do Threes and Fours process grief differently — and what does healthy grieving even look like through an Enneagram lens? What does it mean to have a heavy wing...

What if the reason your closest relationships feel stuck isn't about how much you care — but about how differently you and the people you love communicate? Today, I sit down with Jason VanRuler, therapist, Enneagram Two, and author of Discovering Your Communication Type: The 5 Paths to Deeper Connection and Stronger Relationships, as he introduces us to his P.A.T.H.S. framework — five communication styles he identified through years of working with couples navigating betrayal, teams in conflict, and individuals trying to understand why the same words land so differently depending on who's in the room. Those five type...

What if the very thing driving your success is quietly breaking you?

Brooke Taylor, Enneagram Three, career coach, and author of Healing the Success Wound,  joins me for a searingly honest conversation about achievement, identity, and spiritual hunger.. Brooke grew up in Silicon Valley where worth was measured in gold stars, landed at Google by her early twenties, and found herself drowning in a success she couldn't feel. We talk about the success wound which, as Brooke describes it, is the pain that comes from mistaking productivity and achievement for self-worth — the deeply installed belief that the mor...

Have you ever known where you want to go—but felt mysteriously stuck getting there? In this episode of Typology, I sit down with Dr. Henry Cloud, clinical psychologist, leadership expert, and bestselling author of Boundaries, to talk about his new book, Your Desired Future: The Five Essential Steps That Take You Where You Want to Go.

Together, we explore the intersection of faith, psychology, the Enneagram, self-awareness, and personal growth, and how real transformation begins when we stop shaming ourselves for where we are and start getting curious about what's possible. Henry brings his characteristic wisdom, war...

"Emotions drive 90 to 95% of our unconscious decision-making."

Attia Qureshi is back — and this time, we go deeper.

After her first interview, Attia's insights on persuasion and negotiation were so helpful that Anthony put them to the test in a real-life negotiation and said, "they changed the game." So, we invited her back to go deeper into the ideas behind her book, Never Settle: Persuasion and Negotiation Skills to Get What You Want, and explore how each Enneagram type approaches one of the most important conversations we can have: asking for what we need.But, as At...

Every once in a while, a conversation comes along that makes you pull out your earbuds and stare into the middle distance. This is one of those.

My guest today didn't come to promote a book or launch a course. He's here because he's a good friend with hard-won wisdom — and the rare ability to articulate what's actually going on inside. Meet Brian Boecker, therapist at Restoring the Soul in Denver, Colorado, and an Enneagram Nine who has spent years doing the slow, unglamorous, profoundly important work of finding himself.

We go deep on what it...

What happens when two powerful paths—Buddhism and the Enneagram—sit down for a conversation?

In this episode, Ian welcomes author and Buddhist teacher Susan Piver (The Buddhist Enneagram) to explore the overlap between these two systems. Susan's new book, The Buddhist Enneagram, offers a fresh lens on personality—not as something to fix, but as something to understand, soften, and ultimately hold with compassion.

This conversation goes beyond personality labels and into something deeper: How your patterns form, why they stick, and how awareness—not willpower—is what actually creates change.

If you've eve...

Most of us think we're avoiding hard conversations because we don't know what to say.

But that's not really the problem.

In this episode, Ian and Anthony dive into the real reason we sidestep the conversations that matter most—and it has a lot less to do with skill and a lot more to do with what's happening inside of us.

Because here's the truth: you can have the best negotiation strategy in the world, but if you don't understand the emotional dynamics underneath the conversation, you're going to be dead in the wa...

What if the conversations you're avoiding… are actually the doorway to the relationships you want?

In this replay from our Courageous Conversations series, I sit down with conflict resolution expert James Guinn to explore a truth most of us would rather sidestep: conflict isn't the problem—our style of engaging it is.

Together, we unpack the hidden patterns that shape how you show up when tension rises—whether you withdraw, accommodate, compete, analyze, or collaborate—and how those instincts, often wired beneath your awareness, quietly drive the outcomes of your hardest conversations.

Here's the deal...

Last week, we kicked off our Courageous Conversations series with a fresh look at building emotional confidence. This week, we lay the groundwork for how personality, emotional regulation, and awareness all play into navigating conversations that matter. 

I sat down with Attia Qureshi—an expert in negotiation and persuasion—but what unfolds isn't just about getting what you want. It's about why we want what we want…and what's really driving us underneath it all.

Attia shares a moment of deep rejection from her childhood that led her to build what she calls an "exoskeleton" of stre...

This week, we're kicking off a multi-week series on how to have courageous conversations.  We'll be digging into the foundations of emotional confidence, strategies for negotiation, and how to have difficult conversations. 

Today, we're taking a fresh look at our conversation with Alicia Michelle to learn how to slow down your inner world and regulate your thoughts, your emotions, and your reactions before you ever step into a hard conversation. 

We're talking about building emotional confidence. Not the loud, chest-thumping kind. I mean the quiet, grounded ability to stay present when things get unco...

What happens when the life you built—carefully, faithfully, and very publicly—splits down the middle in a single night?

This week on Typology, we're revisiting one of the most powerful conversations we've had on the show—a replay of my interview with bestselling author and cultural truth-teller Jen Hatmaker.

Jen, an Enneagram Three with a courageous edge that sometimes looks a lot like an Eight, joined me to talk about her memoir Awake and the "before-and-after date" that changed everything—July 11, 2020— when her 26-year marriage ended and the life she knew cracked wide open.

In...

There are some conversations that don't just inform you—they find you. This was one of those for me.

In this episode, I sit down with my friend Dudley Delffs—author, therapist, and a fellow self-preservation Four—and what unfolds is less of an interview and more of an honest, unguarded conversation between two people who've spent a lifetime trying to tell the truth about their lives…and sometimes wondering what it costs to do that.

We talk about the long journey of being a Four—the early years of feeling different, the instinct to hide parts...

Most leaders think workplace problems are about strategy, performance, or communication. But what if the real issue is something deeper—something invisible shaping how people interpret everything that happens at work?

In this episode of Typology, Anthony and I explore how the Enneagram reveals the hidden motivations driving behavior inside teams and leadership groups. When people begin to understand why they—and their colleagues—think, react, and communicate the way they do, everything starts to shift.

We talk about what happens when organizations move beyond personality labels and start using the Enneagram as a practical tool f...

In Part 2 of our conversation on using the Enneagram in therapy, we move from theory to lived experience in the room.

Anthony and I discuss how type can be understood as an adaptive survival strategy shaped by early attachment and trauma—and how that framing reduces shame instead of reinforcing it. We talk about what it looks like when the Enneagram is actually working in session: increased self-observation, greater emotional regulation, and more compassion.

As a therapist, your type doesn't clock out when the session starts, so we dig into the importance of self-awareness and co...

What does it mean to use the Enneagram in therapy responsibly?

In Part 1 of this two-part conversation on Typology, Anthony Skinner and I lay the groundwork for therapists, counselors, and coaches who want to responsibly integrate the Enneagram into clinical practice with wisdom and care. 

Together, we unpack what the Enneagram is—and what it isn't—in the therapy room. It's not a diagnosis. It's not a substitute for evidence-based modalities. And it should never flatten complexity or bypass deeper trauma work.

I also share practical wisdom from decades of work as a thera...

There are conversations that stretch you a little. And then there are conversations that gently but firmly rearrange the furniture in your mind.

This week, I sat down with Keith Kurlander and Will Van Derveer—co-founders of the Integrative Psychiatry Institute—to talk about something that's generating a lot of curiosity and, let's be honest, some anxiety: psychedelic-assisted therapy.

Before you brace yourself, this isn't a hype session. It's a thoughtful, grounded conversation about trauma, the nervous system, and what happens when traditional therapy isn't enough to reach the deepest layers of pain we carry.

In this episode of Typology, I sit down with therapist and author Joe Nucci for a thoughtful, wide-ranging conversation about the Enneagram, mental health, and the growing misuse of therapeutic language in our culture.

Joe—an Enneagram Three—shares his own journey with the Enneagram, the hidden shame dynamics of Threes, and how public success can quietly pull us toward performance instead of integrity. Together, we explore why tools like the Enneagram work best as maps, not MRIs—helpful for self-awareness and empathy, but dangerous when they turn into rigid labels.

We also dig into Joe's...

What happens when Enneagram Eight energy grows up, softens its edges, and learns to lead with both strength and soul?

In this episode of Typology, Ian Morgan Cron sits down with restaurateur, entrepreneur, and conscious capitalism advocate Dan Simons, co-owner of Founding Farmers, for a wide-ranging, deeply human conversation about power, protection, and what it really means to build a culture of care.

Dan is brand-new to the Enneagram—and quickly discovers he's an Eight with a strong Nine wing, a compelling combination that blends moral clarity with empathy, decisiveness with nuance, and fire with ca...

What happens when the worst thing you've been afraid of actually happens—and you're still standing?

In this episode of Typology, I sit down with songwriter Brad Warren—an Enneagram Six, a man in long-term recovery, a husband, a father, and someone who has walked straight through unimaginable grief and come out the other side with humility, humor, and hard-won wisdom. Brad is the kind of person who tells the truth without posturing, who can laugh at himself without diminishing himself, and who understands—deeply—that fear doesn't disappear just because you name it. But naming it does cha...

What happens when the need to appear competent becomes the very thing that disconnects us from others—and from ourselves?

In this deeply honest and surprisingly funny conversation, Ian welcomes author, speaker, and Enneagram Three, Steve Cuss for a wide-ranging dialogue on anxiety, performance, false self, and the quiet freedom that comes with becoming more human-sized. Drawing from Steve's experience as a hospital chaplain, pastor, and leadership consultant, they explore why our most polished coping strategies often come from fear, how predictable patterns keep us stuck, and why anxiety is so contagious in families, churches, and organizations.

What if your most meaningful work begins after you stop striving to prove yourself?

In this warm, wide-ranging conversation, I sit down with old friend, songwriter, filmmaker, and Enneagram Two Andrew Greer for a heartful exploration of loneliness, love, boundaries, creativity, and what it really means to live a good life.

Andrew opens up about the hidden sadness behind the Enneagram Two's gift for connection—the ache that often fuels the desire to help, anticipate, and care for others. Together, we unpack how pride, control, and fear of being a burden can quietly shape relationships, an...

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 re...

With the holidays just around the corner, we're bringing back a conversation that continues to deliver relational gold. Whether you heard it the first time or you're discovering it now, this replay with author and Enneagram teacher Christina Wilcox offers a beautifully practical and deeply compassionate look at how the Enneagram can transform the way we show up for one another during the most emotionally charged season of the year.

In this episode, Christina shares her journey of discovering herself as an Enneagram Six—along with the courage, clarity, and self-understanding that followed. Together, we explore how ea...