Dr. Henry Cloud on Your Desired Future, Self-Awareness, and the Psychology of Change
Release Date: 05/21/2026
When Certainty Collapses: Chasing Francis – Chapter One
Typology
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...
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Enneagram Essentials: Passion and Virtue
Typology
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....
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Enneagram Essentials: Subtypes
Typology
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...
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Enneagram Essentials: Instincts
Typology
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 —...
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Enneagram Essentials: Basic Fears
Typology
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...
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Enneagram Essentials: You Asked, We Answered
Typology
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...
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Good Boundaries and Goodbyes: Lysa Terkeurst exemplifies a Nine Who's Done the Work
Typology
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 walls but communication...
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Replay: Raising Kids Who Want to Come Home with Andy & Sandra Stanley
Typology
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 share how they came to...
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Mailbag: Trauma & Type, Subtypes, Wings, and How We Grieve
Typology
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, and can you access both...
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The Way You Communicate Is Costing You Connection | Jason VanRuler
Typology
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 , 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 types: the Peacemaker, the Advocate, the Thinker, the Harbor, and the...
info_outlineHave 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, warmth, and clinical insight to a conversation about healing, purpose, emotional health, and the practical path from “here” to “there.”
This is a thoughtful and hope-filled conversation for anyone who feels stuck, is navigating change, or wants to better understand the patterns that shape the life they’re living.