Explore every episode of the podcast Typology

What happens when the person everyone sees on the outside doesn't quite match the person you know yourself to be?

Award-winning singer, songwriter, and author Cindy Morgan joins me for a heartfelt conversation about belonging, authenticity, creativity, and the inner world of the Enneagram Four.

Cindy shares how growing up poor and isolated in East Tennessee shaped her identity, why success in the Christian music industry didn't resolve her feelings of being an outsider, and how she eventually began finding her people and embracing her own story.

Together, we explore the often-overlooked self-preservation subtype of the Enneagram Four, including its remarkable resilience, fierce work ethic, and tendency to suffer quietly.

We also discuss Cindy's novel, The Dogwood Gospel, and how it explores childhood trauma, identity, and the longing to know where we come from.

We share plenty of laughs, stories from our songwriting friendship, and a beautiful reflection on why gratitude may be one of the greatest gifts of growing older.

Whether you're a Four or simply someone who's ever struggled to feel at home in your own skin, this conversation is for you.

What if shame isn't the enemy we've always thought it was? What if, instead of trying to silence it, we learned to listen for what it might be telling us?

This week, I sat down with Dr. Frank Spinelli, an Enneagram Eight and the author of The Shame Compass: A Radical Framework for Trauma Healing and Self-Acceptance. Frank has spent years thinking about the ways trauma and shame shape our lives and he knows this territory personally. In our conversation, he shares how the armor we build to protect ourselves can help us survive, but can also keep the people who love us from ever seeing who we really a

Dr. Spinelli offers a different way to understand shame. Rather than treating it as proof that something is wrong with us, he invites us to see it as information: a signal that something deserves our attention. We talk about his COMPASS framework for working with shame, why learning to pause can change the course of a difficult moment, and how to separate the facts of a situation from the harsh stories we tell ourselves.

We also get into the Enneagram Eight's relationship with strength, anger, control, and vulnerability. Frank makes a point I think many of us need to hear: our strength may not be the problem. The belief that we have to carry everything alone might be.

And underneath all of it is the importance of connection. Shame thrives in isolation. Healing asks us to risk being known.

Whether shame is something you've wrestled with for years or you're only beginning to recognize its voice, I hope this conversation helps you meet yourself with a little more honesty, compassion, and courage.

In this episode:
• Why the armor we build to survive can eventually keep us from being fully known
• How shame can function as a signal rather than an indictment
• The difference between toxic shame and the kind of shame that calls us back to our values
• Frank's seven-stage COMPASS framework for developing shame literacy
• Why pausing is a skill we can—and should—practice before we're activated

What does it actually mean to become a person of deep character in a culture obsessed with personality, platform, and performance?

On this episode of Typology, Ian Morgan Cron sits down with therapist, spiritual director, professor, and author Dr. Chuck DeGroat to explore the slow and courageous work of becoming whole.

Drawing on his new book, Who You're Becoming: The Slow and Courageous Work of Cultivating Character in a Narcissistic Age, Chuck invites us to look beneath the image we present to the world and consider the person we are becoming.

Together, Ian and Chuck explore authenticity, vulnerability, spiritual formation, leadership, and the challenge of cultivating genuine character in a world that often rewards the opposite. It's a conversation about telling ourselves the truth, moving beyond performance, and embracing the deeper work of growth.

Because becoming whole isn't about building a better image. It's about becoming a more integrated, honest, and courageous human being.

In this episode, we explore:

• What it means to cultivate deep character in a culture of performance

• The difference between appearing authentic and doing the work of becoming whole

• Why vulnerability and honest self-examination matter

• The relationship between spiritual formation, leadership, and character

• How we can become more intentional about the people we are becoming

Chuck DeGroat serves at Western Theological Seminary and is the founder of the Soul Care Collaborative. He is a therapist, spiritual director, professor, and author whose work explores the intersection of psychology, spiritual formation, trauma, leadership, and faith.

Listen in, reflect on who you're becoming, and join us for another conversation about the mystery of personality and the great human adventure.

Subscribe to Typology for more conversations about the Enneagram, self-awareness, and the work of becoming who we were created to be.

None of us becomes who we are on our own. We carry the stories, wounds, wisdom, and unfinished hopes of the people who came before us. Sometimes we recognize those inheritances; sometimes they show up in us before we even have words for them.

This week on Typology, Anthony and I sit down with J.S. Park, hospital chaplain and author of We Are Made of Us, to talk about the complicated, beautiful truth that understanding ourselves means getting curious about the people and stories that shape us. Joon's work has brought him alongside people at life's most vulnerable thresholds, where family histories and old patterns often come into view. He invites us to look at our own stories with a little more curiosity and a little less judgment.

Whether you're a Two, a Four, or simply someone whose family story is still unfolding, I hope this conversation offers you a little insight, compassion, and room to breathe.

In this episode:

• How culture and family shape the way we understand our Enneagram type
• The "June bow": why we sometimes rush people through grief
• Moving beyond codependence and independence toward interdependence
• A more compassionate question to ask about difficult family relationships
• Listening to our aging parents and honoring the stories they carry

Resources:
We Are Made of Us by J.S. Park (releases 10/20/26)
J.S. Park on Instagram 
J.S. Park Website

Take the Typology Institute Enneagram Assessment

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.

ABOUT PAUL YOUNG

Wm. Paul Young was born in Canada and raised among a Stone Age tribe by his missionary parents in the highlands of former New Guinea. He suffered great loss as a child and young adult and now enjoys the "wastefulness of grace" with his family in the Pacific Northwest. He is the author of Lies We Believe About God and the New York Times bestsellers The Shack, Cross Roads, and Eve.

The Return of the Shack
The Shack
Website
Instagram
Facebook

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.

ABOUT DRS. LES AND LESLIE PARROTT

Drs. Les and Leslie Parrott are #1 New York Times bestselling authors and psychologists. Their books include The Love Language That Matters Most; Health Me, Healthy Us; and the award-winning Saving Your Marriage Before It Starts. Their pioneering assessments have been used by millions and include the free MyHeartChart.com. Their work has been featured in the New York Times and USA Today as well as on CNN, Good Morning America, TODAY, The View, and Oprah. They live in Seattle and can be found online at LesandLeslie.com.

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.

ABOUT AINSLEY BRITAIN:
Ainsley Britain is an Author, Podcast Host, and Enneagram Coach dedicated to helping young adults build confidence and foster healthy relationships. A Cajun at heart and native of Lafayette, Louisiana, Ainsley's journey took her through New York City and Nashville, shaping her relationships, experiences, and career. Her book, The Enneagram for Teens, offers young adults an introduction to the Enneagram during formative years of their lives and her podcast, Wild Confidence, shares insights from Ainsley's experiences, aiming to empower others. Now residing in Baton Rouge with her family, Ainsley embraces the vibrant culture of South Louisiana.

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.

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 tools, and the slow, non-linear work of learning to stop diminishing herself to cover for someone else's worst behavior. This episode is essential listening — not only for Nines but for anyone who has ever struggled to say no, set a limit, or walk away from a relationship that was taking more than it was giving.

In this episode, Ian and Lysa discuss:

• The Nine's tendency to self-forget — and how that looks in conflict, breakups, and daily decisions
• Lysa's defining mantra: "I will no longer diminish the best of who I am to cover up for the worst of who someone else is."
• Practical scripts for saying no: "While my heart says yes, the reality of my time makes this a no."
• The difference between compassion and clarity — and why a Nine needs both
• How codependency shows up differently in Twos vs. Nines (and why they're so often confused)
• The dangerous pattern of spiritual bypassing — and how Lysa's therapist called it out

Especially rich for Enneagram Nines and Twos — but every type will find something here worth writing down.

To learn more about Lysa Terkeurst visit www.lysaterkeurst.com or find her on Instagram and Facebook. 

You can also pre-order her new book "Making Peace With What I Can't Control" here. 

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 define the "win" of parenting as raising kids who want to be with you and with each other when they no longer have to be. That one sentence is worth the price of admission. We also explore the role of discipline, apology, regret, repair, and why humility may be one of the greatest gifts parents can offer their children.

Whether you are raising toddlers, teenagers, adult children, or looking back with a few regrets and a lot of love, this conversation is full of wisdom, grace, and hope.

In this episode, we explore:

• Why parenting is ultimately about relationships, not rules
• How Enneagram Ones parent—and what happens when two Ones raise a Seven
• The difference between punishment and discipline
• Why learning to repair broken relationships is essential for lifelong happiness
• How parents can live with tension without trying to solve everything
• Why "progress, not perfection" may be the mercy every parent needs

So pour a cup of coffee, take a deep breath, and listen in. This is one you'll want to pass along to every parent you know.

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 wings for growth? And for the Ones in the room — what do you actually do with all that repressed anger?

Whether you're new to Typology or you've been with us for years, this one is worth your time.

Have a question of your own? Send it to wendy@ianmorgancron.com and you might hear it answered on our next mailbag episode.

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 types: the Peacemaker, the Advocate, the Thinker, the Harbor, and the Spark. 

The nine Enneagram types map fascinatingly onto these five communication styles, and we walk through each type together. We talk about blind spots (every communication style has one), what happens to our style under stress and in conflict, and why the most generous thing you can do in any relationship is learn to speak your people's language rather than demanding they speak yours.

Jason also shares honestly from his own marriage — he's a Harbor married to a Thinker — and what changed when he learned to stop reading his wife's precision questions as opposition and started hearing them as her version of love.

Whether you're an Enneagram enthusiast, a couples therapist, a team leader, or just someone who's tired of feeling unseen in conversations, this episode is for you.

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 more you produce and achieve, the more worthy of love and belonging you become.

This wound isn't just for Enneagram Threes. It's a human condition — and it shows up differently depending on your type, your culture, your family system, and what "success" looks like in your particular world. 

We talk through Brooke's five types of unfulfilled achievers — the grinder, the hider, the seeker, the work-hard-play-hard, and the pleaser — and I couldn't help mapping those to the Enneagram types in real time. We also get into the distinction between the true self, the wounded self, and the socialized (or protector) self — a framework rooted in Internal Family Systems and gestalt psychology that I think will resonate deeply with longtime Typology listeners.

Whether you're a Three or you love one, this episode is for you.

Guest Bio:

Brooke Taylor is a certified career coach, speaker, and the author of Healing the Success Wound. A self-identified Enneagram Three, Brooke built her coaching practice specifically for women navigating the intersection of ambition, identity, and fulfillment — though her framework applies broadly across genders. Her research includes a survey of more than 5,000 high-achieving professionals who identified as unfulfilled, which forms the empirical backbone of her five-type model of the unfulfilled achiever. A veteran of Google and a long-term member of recovery communities, Brooke brings both lived experience and rigorous research to her work. She is the founder of the Lined Ambition framework and writes and coaches at the crossroads of psychology, spirituality, and career development. Learn more at brooketaylor.co.

Healing the Success Wound is available now wherever books are sold.

Find Brooke at https://brooketaylorcoaching.com.

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, 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.

"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 Attia explains, negotiation isn't just something that happens across a boardroom table. It happens every day – with our spouses, our kids, our coworkers, our neighbors, and perhaps most importantly, within ourselves. Before we ever make an ask, we have to face the internal stories, emotions, fears, and assumptions that often keep us from speaking up in the first place.

In this episode, we explore how different Enneagram types navigate negotiation, conflict, emotional regulation, self-advocacy, and the art of creating value without damaging relationships. We unpack why some types avoid the ask, why others over-assert, why some need more clarity around what they actually want, and how every type can grow in confidence, courage, and self-awareness.

You'll learn:

• How emotions shape the way we ask – or don't ask – for what we need

• How to identify and label your emotions so they stop driving your decisions unconsciously

• The worst-case scenario exercise that builds resilience and inoculates you against fear

• What each Enneagram type brings to the negotiation table — where they shine, where they get stuck, and what to do about it

• A breathing technique that signals your nervous system it's safe before a high-stakes conversation

You can learn more about Attia and grab her free resource for Typology listeners, which includes a breakdown of each Enneagram type's negotiation strengths, blind spots, and exercises at https://attiaqureshi.com/typology. 

Never Settle: Persuasion and Negotiation Skills to Get What You Want by Attia Qureshi and John Richardson is available now wherever books are sold.

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 really means to belong versus simply fit in, why desire is so terrifying to name out loud, and how anger — when you stop running from it — turns out to be something closer to a life force than a liability. Brian is disarmingly honest about the ways he's learned to disappear, the slow work of becoming solid, and what it looks like to finally walk through the door you've been standing in front of your whole life.

Whether you're a Nine or you love one, this conversation will give you a richer, more compassionate picture of what's actually going on beneath that calm surface.

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 ever felt stuck in your reactions, overwhelmed by your emotions, or quietly convinced you're "doing life wrong," this episode offers a different path forward.

Together, they unpack:

• How the Enneagram and Buddhism overlap (and where they challenge each other)

• The difference between mindfulness and awareness (and why both matter)

• How meditation helps you notice your reactions without being ruled by them

• Why trying to "fix yourself" often backfires—and what works instead

• How Enneagram subtypes shape conflict, connection, and relationships

As always, this isn't about becoming someone else. It's about becoming more fully who you already are—with a little more grace along the way.

Susan Piver is a Buddhist teacher, meditation instructor, and author of The Buddhist Enneagram. Her work bridges ancient wisdom and modern psychology, helping people cultivate compassion and awareness in everyday life.

If this episode resonates, follow the show so you don't miss future conversations on the Enneagram, relationships, and spiritual growth.

Know someone who's deep into the Enneagram—or stuck in their patterns? Send this their way. It might be exactly what they need to hear.

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 water.

As part of our Courageous Conversations series, this episode serves as the emotional intelligence companion to negotiation—helping you move from avoidance to clarity, from anxiety to grounded confidence.

Ian unpacks:

• Why we were never taught how to have hard conversations (and what we learned instead)

• The "fool's choice" that keeps us stuck between silence and relational fallout

• How the stories we tell ourselves quietly shape our emotions and reactions

• The three common narratives (victim, villain, helpless) that sabotage connection

• A simple but powerful 5-step framework to actually have the conversation

• What to do when things go sideways—and how to restore safety in real time

Along the way, you'll discover that the goal isn't just to "say it better"—it's to show up differently.

Because hard conversations don't ruin relationships. Avoiding them does.

So as you listen to this episode, ask yourself: "What's one conversation you've been avoiding—and what would it look like to walk into it just a little more prepared?"

**This episode is part of our ongoing Courageous Conversations series—where we're learning how to speak honestly, navigate tension, and build stronger, more trust-filled relationships in the places that matter most.

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: every difficult conversation is a negotiation. Not just of outcomes, but of needs, emotions, and meaning. And if you don't understand your default conflict style—or the style of the person across from you—you'll keep talking past each other, escalating what could've been resolved.

James brings a practical framework for identifying what actually triggers conflict (hint: it's not always what you think), and I connect the dots to the Enneagram—because knowing your type isn't just about self-awareness, it's about relational wisdom in real time.

We also wrestle with a deeper question:
How often is the conflict really about the issue… and how often is it about something underneath—process, expectations, or old emotional wounds we've carried into the room?

If you've ever walked away from a conversation thinking, "That did not go how I hoped," this episode will give you a new playbook.

Because courageous conversations aren't about winning.
They're about understanding, adapting, and learning how to meet people where they are—without losing yourself in the process.

And that, my friends, is a skill worth building.  

Tune in next week as Anthony and I talk through a simple, practical framework for having difficult conversations. 

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 strength. And as we talked, it became clear how many of us are still walking around with some version of that same armor—negotiating, relating, and even loving from a place of protection rather than connection.

We explored how that plays out in everyday life—how we handle conflict, how we ask for what we need, how we respond when we feel threatened or unseen. And what I appreciated most about Attia is that she doesn't just talk about tactics—she talks about transformation. About moving from control to curiosity. From winning to understanding. From guarding yourself…to actually showing up.

This is such an interesting topic that we invited Attia back for a second episode, where we go even deeper into her book Never Settle and unpack how her core negotiation strategies apply to each Enneagram type. Think of it as taking everything we talk about today and making it incredibly practical and personal for how you move through the world.

And to help you get started, Attia has put together a fantastic Negotiation by Enneagram Type cheat sheet you can grab at attiaqureshi.com/typology.

Pull up a chair. This one's going to get under the hood—in the best possible way.

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 uncomfortable…when the stakes are high, the emotions are rising, and every instinct in your body is telling you to either shut down or go on the attack.

Here's the truth: every meaningful relationship—at home, at work, in leadership—requires negotiation. Not just contracts and deals, but expectations, needs, boundaries, and repair. And if you don't have emotional confidence, those conversations can go sideways fast.

That's why today's guest, Alicia Michelle, is such a gift. She brings wisdom, honesty, and a kind of steady clarity that helps us see what's really happening underneath our reactions—and how to show up differently.

Because the goal isn't to win the conversation. It's to stay in it…with courage, curiosity, and just enough self-awareness to not blow the whole thing up.

So if you've been avoiding a conversation, replaying one that didn't go well, or gearing up for one you know is coming—this episode is for you.

Let's dive in.

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 this conversation, we explore what it means to wake up in midlife:

• to grief and betrayal,

• to shedding scripts you never consciously chose,

• to loosening your grip on approval,

• and to discovering what actually matters in the second half of life.

We also dig into how Threes navigate identity, success, and failure—especially when life refuses to follow the plan. Jen shares how therapy, embodiment work, and radical honesty helped her rebuild—not for optics, but for something sturdier and truer.

If you're in a season of change—or if life has recently pulled the rug out from under you—this episode still hits with the same quiet force. Think of it as a hand on your shoulder and a light for the next few steps.

ABOUT JEN HATMAKER

Jen Hatmaker is a bestselling author, award-winning podcaster, speaker, and fierce advocate for women living in freedom and agency. With 14 books—including four New York Times bestsellers—along with her beloved For the Love podcast, Jen Hatmaker Book Club, and more, she reaches millions with her signature mix of humor, vulnerability, and wisdom. Her newest book, AWAKE: A Memoir, (released on September 23, 2025), chronicles her raw, real-time journey through the shocking end of her 26-year marriage and surprising reinvention. She lives in a creaky old farmhouse, loves 90s country, and drinks Almond Joy creamer like it's a personality trait. Find her at JenHatmaker.com.

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 of your story, and the slow, sometimes painful work of learning how to bring those parts into the light. Along the way, we wander into territory that might feel familiar: creativity, envy, addiction, belonging, and that quiet, persistent question many of us carry: What have I done with my life?

And yet, this isn't a heavy conversation—it's a human one. There's laughter, there's tenderness, and there are a few moments where something deeper breaks through…the kind of moments that remind me why I love doing this work in the first place.

If you've ever felt like you don't quite fit—even in rooms where you clearly do…
If you've wrestled with whether your story is too much—or somehow not enough…
Or if you're trying to make peace with your past without losing who you are in the process…

I think this conversation might meet you right where you are.

Come listen.

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 for leadership, conflict, and culture.

If you lead people, work on a team, or have ever wondered why certain workplace dynamics keep repeating themselves… this conversation might change the way you see your office forever.

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 countertransference, explore how the Enneagram can either heal or harm in couples work, depending on whether it increases curiosity or contempt.

Whether you're a clinician or someone doing your own inner work, this episode invites you to hold the Enneagram lightly—and people reverently.

When it's used well, it doesn't replace therapy.

It deepens it.

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Download the free Therapist Discussion & Reflection Guide

Check out the Typology Institute Enneagram Assessment

Follow Ian on social at @ianmorgancron and @typologypodcast

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 therapist, priest, and Enneagram teacher, offering guidance for using the Enneagram in a way that increases compassion rather than contempt, flexibility rather than rigidity, and insight rather than shame. 

At its best, the Enneagram helps us see people not as problems to solve, but as stories shaped by fear, longing, and adaptation. Used wisely, it becomes a powerful reflective tool that deepens emotional intelligence, strengthens therapeutic relationships, and supports real transformation.

When the Enneagram is used well, it doesn't replace therapy.

It deepens it.

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.

We explored how trauma shapes our personalities, how it imprints on the body, and why insight alone often doesn't create lasting change. As someone who cares deeply about the Enneagram and recovery, I found this especially compelling. So much of our personality structure is built around adaptation—strategies that once kept us safe but now quietly run the show.

Keith and Will explain how psychedelic-assisted therapy, when done legally and in carefully structured clinical settings, may help people access and heal places that feel otherwise unreachable. We also talk about the risks, the ethics, and the importance of discernment.

This isn't about chasing peak experiences. It's about healing what's unfinished.

If you've ever felt stuck in patterns that insight alone couldn't untangle… if you've wondered whether deeper healing is possible… this conversation might open a door.

LEARN MORE ABOUT WILL AND KEITH

WILL VAN DERVEER, MD, is a leader in the adoption of integrative psychiatry practices to treat mental health issues. He is cofounder of the Integrative Psychiatry Institute and Integrative Psychiatry Centers and cohost of The Higher Practice Podcast for Optimal Mental Health. He has published research on MDMA-assisted psychotherapy. Dr. Van Derveer has published research on MDMA-assisted psychotherapy for PTSD [1] and written book chapters in the fields of ketamine-assisted psychotherapy and other clinical applications of psychedelic compounds. His passion is finding effective relief from psychological suffering using a vast array of the most natural approaches possible. In addition to traditional medical training, He is a meditation instructor and has trained in shamanism, EMDR, somatic experiencing, internal family systems, cognitive behavioral therapy, and hypnosis.

KEITH KURLANDER, MA, LPC, is cofounder of the Integrative Psychiatry Institute and Integrative Psychiatry Centers and cohost of The Higher Practice Podcast for Optimal Mental Health. He graduated Naropa University in 2005 with a master's degree in Transpersonal Counseling Psychology, and he has practiced integrative psychotherapy and coaching with individuals, couples and groups for over 15 years. Keith's work as a coach focuses on celebrities, influencers, entrepreneurs, and CEOs who want to make huge changes in their lives, overcome long-standing patterns, and achieve greater levels of fulfillment. Keith specializes in helping individuals achieve optimal mental health and peak potential.

Social Links & Website (for promotional use)

Website - Keith Kurlander, MA, LPC 
Instagram (Keith) | Instagram (Will)
LinkedIn (Keith) | LinkedIn (Will)
Psychedelic Therapy: A Revolutionary Approach to Restoring Your Mental Health and Reclaiming Your Life (Shambhala; March 31, 2026), 

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 new book, Psycho Babble, discussing how clinical terms like narcissist, OCD, and trauma have become everyday adjectives—and what it costs us when labels replace discernment, curiosity, and real relationship.

This is a grounded, honest conversation about growth, character, and what it actually means to become a healthier version of yourself—without turning self-awareness into self-avoidance.

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ABOUT JOE NUCCI

Joe Nucci is an expert in breaking down how people talk about mental health. He's a psychotherapist who corrects widely misused terms, adds valuable nuance and explains complex ideas in ways anyone can understand. He can take a mental health lens to any hot button issue. Anyone who listens to him will walk away knowing themselves and others a little better. Joe reached over 10 million people in his first 6 months of posting content. His book "Psychobabble" explores why mental health information is so confusing to navigate and how to more easily understand different perspectives about mental health. He also has an upcoming podcast, being produced by Luminary Podcasts, where he will take deeper dives into the different mental health topics that he explores on Instagram, Facebook and Tiktok @joenuccitherapy

Pscyhobabble: Viral Mental Health Myths & the Truths to Set You Free

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 calm. Together, Ian and Dan explore how Eights aren't just challengers—they're often defenders: leaders shaped by early experiences of injustice who instinctively stand up for the vulnerable.

Along the way, they talk candidly about:

• Why anger can be a tool rather than a liability when it's consciously harnessed

• How leadership failures are often listening failures (and the three most powerful words a leader can say)

• How putting emotional well-being on equal footing with profit actually increases performance, retention, and long-term value

• What a healthy workplace should feel like when you walk through the door (hint: think Labrador retriever, not shark tank)

This is a masterclass in evolved leadership and a hopeful vision of capitalism done with conscience. If you're a leader, an Enneagram Eight, or someone longing for work cultures that don't crush the human spirit, this conversation will leave you both challenged and encouraged—in the best possible way.

Listen in and pull up a chair. There's a seat for you at this table.

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About Dan Simons

Dan Simons is regarded as a leading voice in mission-driven business practices, known for championing people-centric culture and responsible industry standards while developing systems that deliver profitability. He and his partner, Michael Vucurevich, are Co-Owners of Founding Farmers Restaurant Group in partnership with the North Dakota Farmers Union. Their goal is to generate profits for American family farmers, earn farmers a larger share of the food dollar, and influence the sourcing decisions of suppliers and others in the hospitality industry. They operate eight sustainably run restaurants, one DC-based distillery, and a full service catering and event design company. He teaches courses at The George Washington University, hosts a podcast (Founding DC), and sits on the advisory boards of the DC chapter of Conscious Capitalism, OpenTable, and the Health Action Alliance Women's Health at Work Program. He blogs at www.DanSimonsSays.com and can be found across most social channels @DanSimonsSays. Visit https://www.dansimonssays.com/ to learn more.

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 change the game.

We talk about the Enneagram Six's instinct to scan the horizon for danger, to rehearse conversations that never happen, and to catastrophize not because they're weak—but because they care. A lot. Brad shares how losing a child forced him to face his worst fears head-on, and how recovery, faith, and accountability helped him learn the difference between imagined catastrophe and lived reality. There's a kind of quiet courage in the way he describes trusting God—not a God who's looking to smite him, but one who's patiently inviting him to rest.

Along the way, we explore humor as both a survival strategy and a spiritual practice, the surprising connection between humility and laughter, and how Sixes learn to move from fear-driven vigilance to faith-filled presence. We also touch on marriage, loyalty, religious deconstruction with gratitude instead of bitterness, and the life-saving power of people who are willing to tell you the truth when your mind is lying to you.

This episode is funny, tender, honest, and deeply human. It's about fear—but it's even more about trust. And what it looks like, day by day, to choose it anyway.

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About Brad Warren

Brad Warren is a Nashville-based songwriter and artist best known as one half of the hitmaking Warren Brothers. He has co-written major country hits recorded by Tim McGraw, Toby Keith , Keith Urban, Faith Hill , Martina McBride, Dierks Bentley, Jason Aldean and more.

Brad is also the host of the Good Grief Good God podcast. He and his wife Michelle lost their oldest son Sage in 2020 and the podcast is in honor of him. Brad covers an array of other topics (recovery, God, mental and physical health, and The Music Business) as well as grief. Guests have ranged from Sheryl Crow and Amy Grant to Scott Hamilton and Charles Esten.

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.

Along the way, they unpack the Enneagram Three's drive to succeed, the exhaustion of self-presentation, the difference between ambition and authenticity, and why true maturity looks a lot like being relaxed—no masks required. Expect stories, laughs, hard-earned wisdom, and a refreshing reminder that you don't have to win the room to belong in it.

If your nervous system needs a deep breath and your soul could use some permission to stand down from proving itself, this episode is for you.

About Steve Cuss

Steve Cuss, M.Div. is a pastor, former chaplain, and founder of Capable Life, which helps people lower internal and relational anxiety in the workplace and homeplace. Steve is a Spiritual Care Professional in the Association of Clinical Pastoral Education, holding 1600 hours of supervised ministry in CPE and a Masters degree focusing on Family Systems Theory and Theology. Steve, his wife, Lisa, and their two sons and a daughter live in Erie, Colorado.

Connect with Steve at:

Website: https://capablelife.com and https://stevecusswords.com

Soul Care Intensives: https://capablelife.com/pages/intensives

Podcast: Being Human with Steve Cuss

Instagram | X 

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, and how learning to receive may be the most courageous spiritual practice of all.

We also dive into Andrew's new book, More Than a President, and explore Jimmy Carter as a quintessential Enneagram One—principled, disciplined, justice-driven, and far more impactful after the presidency than during it.

This episode is a meditation on personality, vocation, and maturity—on shifting focus from résumé to soul, from achievement to love, from striving to rest. It's thoughtful, funny, deeply human, and quietly challenging.

Pull up a chair. This one stays with you.

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About Andrew Greer

Author, musician, and filmmaker, Andrew Greer has published three books, released multiple chart-topping recordings, and directed the PBS documentary Plainspoken, a film inspired by the lives of Jimmy and Rosalynn Carter and their neighbors in Plains, Georgia. A Texas native, and longtime Nashvillian, Greer now makes his home in Plains.

Website: https://www.andrew-greer.com/
New Book: http://sundayswithjimmycarter.com/
Instagram: https://www.instagram.com/andrewbgreer/
Facebook: https://www.facebook.com/agreermusic

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.

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 each type navigates holiday stress, joy, expectation, and connection…and how you can care for the people you love in ways that truly meet them where they are.

You'll learn:

• How to support friends and family of every Enneagram type through the busyness and emotional intensity of the holidays

• Practical tools for managing social anxiety, especially for Sixes

• Why presence and gratitude matter so deeply, particularly for Fours—and how all of us can cultivate them

• Simple, insightful practices for building healthier, more attuned relationships this time of year

Whether you're hoping to deepen your emotional intelligence, strengthen your closest relationships, or simply bring more kindness and awareness into your holiday rhythms, this episode is a gift worth unwrapping again.

Lean in, listen well, and let the Enneagram help you love the people in your life a little better this Christmas.

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P.S. For a limited time, take 40% off all Enneagram Courses through the holidays.  Use the discount code HOLIDAY40 here. 

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

On this episode of Typology, I sit down with bestselling author and beloved cultural commentator Jen Hatmaker to talk about her stunning new memoir, Awake. Jen, an Enneagram Three with a courageous streak that can look a whole lot like an Eight, opens up about the "before-and-after date" that changed everything—July 11, 2020—when her 26-year marriage ended, and her whole world cracked open.

Together, we explore what it means to wake up in midlife:

• to grief and betrayal,

• to leaving behind scripts you never chose,

• to freedom from needing to be liked,

• to discovering what really matters in the "second half of life."

We dive into the Enneagram and the unique way Threes navigate identity, image, success, and failure—especially when life doesn't cooperate with the plan. Jen shares how therapy, embodiment work, and raw honesty helped her rebuild, and why this memoir isn't about spectacle, but about hope.

This is a conversation about midlife transition, spiritual awakening, and the quiet miracle of becoming more fully yourself—right when you thought everything was falling apart.

If you're navigating change, heartbreak, faith shifts, or a midlife renaissance of your own, this episode will feel like a hand on your shoulder and a light on the path.

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ABOUT JEN HATMAKER

Jen Hatmaker is a bestselling author, award-winning podcaster, speaker, and fierce advocate for women living in freedom and agency. With 14 books—including four New York Times bestsellers—along with her beloved For the Love podcast, Jen Hatmaker Book Club, and more, she reaches millions with her signature mix of humor, vulnerability, and wisdom. Her newest book, AWAKE: A Memoir, (released on September 23, 2025), chronicles her raw, real-time journey through the shocking end of her 26-year marriage and surprising reinvention. She lives in a creaky old farmhouse, loves 90s country, and drinks Almond Joy creamer like it's a personality trait. Find her at JenHatmaker.com.

CONNECT WITH IAN

Follow Ian on Facebook or Instagram at @ianmorgancron and @typologypodcast.
Check out Ian's website at www.ianmorgancron.com

**Interested in a 30-minute one-on-one virtual coaching session with Ian?  Fill out this intake form and we'll be in touch. 

This week on Typology, we welcomed the incomparable Lynn Smith—former national news anchor turned communications strategist, executive coach, and proud (and newly discovered) Enneagram Three with a Two wing. And friends… buckle up. This conversation is a masterclass in emotional intelligence, presence, and what it means to pursue success without losing yourself in the chase.

Fresh off taking the Typology Assessment, Lynn joined us in that familiar Three-ish blend of humor, candor, and high-octane energy, joking that the results made her want to immediately call her therapist. What unfolded from there was a remarkably vulnerable exploration of people-pleasing, approval-seeking, identity, and the hidden costs of a lifetime spent earning applause.

Lynn pulled back the curtain on her years in broadcast news—an industry where worth is measured in seconds, headlines, and flawless delivery—and revealed the deeper story beneath her polished exterior: a lifelong drive to achieve, a tenderness inherited from her family's immigrant narrative, and a powerful desire to help others communicate with confidence and authenticity.

But the real gem of this episode is Lynn's groundbreaking work on what she calls "the brain bully."

That inner critic.
That saboteur whispering that you're one misstep away from failure.
That internal voice Threes know far too well.

Lynn not only names it—she teaches you how to outsmart it.

Her framework for dismantling fear and building resilient confidence is practical, empowering, and deeply human. And when she reveals her own brain bully's name—"Bob"—you can't help but laugh and exhale. Sometimes the most powerful breakthroughs come with a wink.

We also wandered into a juicy conversation about magnetism versus authenticity, why your energy enters a room a full tenth of a second before you do, and how the Enneagram can radically improve communication across teams, industries, and families.  

Connect with Lynn Smith at www.lynnsmith.com or on socials at @lynnsmithtv

CONNECT WITH IAN

Learn more about the Enneagram at www.ianmorgancron.com or follow Ian at @ianmorgancron and @typologypodcast on Instagram and Facebook

P.S. Interested in a 30-minute one-on-one virtual coaching session
with Ian? Fill out our interest form here.

German-born spiritual teacher and self-help author Eckhart Tolle once wrote, "Acknowledging the good that you already have in your life is the foundation for all abundance."

 I found this to be true in my life as well, and as it turns out, expressing gratitude isn't just a sound spiritual practice. It's essential to our emotional and physical well-being.

 According to a recent study performed at Harvard Medical School, "Gratitude is strongly and consistently associated with greater happiness. Gratitude helps people feel more positive emotions, relish good experiences, improve their health, deal with adversity, and build strong relationships."  

 How can you reap the benefits? While there are many beneficial exercises that can help you cultivate an attitude of gratitude, such as journaling, morning or evening reflections, and performing acts of kindness, many people focus their thoughts outward (Ex: I'm grateful for my children, a roof over my head, my job, etc.).It's easy to lose sight of the good in ourselves.

Instead, let's focus inward. Tune in as Anthony and I share what we're grateful for about each Enneagram type and why you should be too.

What happens when an Enneagram Two (or…maybe a Four?) takes a deep dive into the ache beneath our desire to be good, loved, and whole?

This week, I sit down with Heath Hardesty, pastor and author of All Things Together: How Apprenticeship to Jesus Is the Way of Flourishing in a Fragmented World. What begins as a conversation about the Enneagram Two's longing to help soon unfurls into an exploration of the soul — the ache for beauty, the mystery of shame, and what it means to live authentically before God.

Together we explore:

• The difference between helping and hiding

• Why our "ache" might actually be a form of divine homesickness

• How beauty, poetry, and the transcendent lead us toward wholeness

• What dies — and what's reborn — as we grow older and surrender our false selves

• The sacred invitation to move from doing ministry to stewarding mystery

It's equal parts theology, therapy, and literary love letter. Whether you're a Two, a Four, or simply a human being trying to make sense of your inner world, this episode will remind you that becoming whole is less about striving and more about awakening.

🎙️ Listen now and discover the sacred ache that pulls us home.

ABOUT HEATH HARDESTY

Heath Hardesty is the author of All Things Together: How Apprenticeship to Jesus is the Way of Flourishing in a Fragmented World (Multnomah; 10/14/25). He serves as the lead pastor of Valley Community Church and is the founder of Inklings Coffee & Tea in the heart of downtown Pleasanton, California.

Heath grew up in a blue-collar home and was a plumber's apprentice in Colorado before becoming a pastor on the edge of Silicon Valley where he, his wife, and four kids now reside.

He holds degrees in literature, leadership, biblical studies, and theology from the University of Colorado Boulder and Western Seminary in Portland. Visit him on IG@heathhardesty.

In this heartfelt, humorous, and deeply human conversation, Ian sits down with longtime friend — artist, filmmaker, professor, and Enneagram Seven — Steve Taylor. You may know him as the legendary provocateur who "invented irony for Christians," but in this episode, we explore the terrain beneath the creativity, the energy, and the relentless forward motion that has defined so much of his life.

Together we wade into the deeper waters of the second half of life — aging, character, grief, spiritual maturity, limitations, and the sacred invitation to move from doing to being. Steve speaks candidly about the shifting landscape of life at 67:

• the habits that no longer serve him

• the tender emergence of compassion

• learning to sit with grief rather than outrun it

• the uncomfortable art of slowing down

• how filmmaking and teaching have reshaped his inner life

• and the courageous (and often comical) struggle of a Seven learning to live in the present moment

We talk about marriage, mortality, the ache of unfinished dreams, the sweetness of gratitude, the pains and gifts of aging, and the spiritual practices that are slowly rewiring Steve's relationship with presence.

Tune in to hear this rich conversation about Enneagram transformation, emotional intelligence, creativity, and the inner work of becoming whole.

ABOUT STEVE TAYLOR

Steve Taylor is a filmmaker, writer, producer and recording artist who earned his "Renaissance Man" stripes (Prism Magazine) from a body of work that's garnered him multiple Grammy, Billboard, Telly, Addy and Dove awards and nominations. A southern California native, he was raised in Denver, Colo., and studied music and film at Colorado University. In 1983, Taylor began a career as a recording artist that spanned 12 years, selling over one million albums worldwide and garnering him two Grammy nominations for "Meltdown" (1984) and "Squint" (1993). In the process, he made history as the only artist to twice win Billboard Music Video Awards for self-directed music videos. As a concert artist, Taylor headlined four international tours, including acclaimed appearances at L.A.'s Universal Amphitheater and London's Hammersmith Odeon. He was also lead singer in the MCA-signed modern rock band Chagall Guevara.

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What happens when two high-achieving Enneagram Threes sit down with an Enneagram Four? You get an electric, honest, and surprisingly tender conversation about ambition, fear, and what it really means to live courageously.

In this episode, Ian sits down with Jenny Wood, former Google executive and author of Wild Courage: Go After What You Want and Get It, and her Chief of Staff, Carlina Daugherty, for an unfiltered look at the drive and depth behind the Enneagram Three. Together, they explore:

·       Why fear — not talent — is often the real barrier to success

·       The nine "wild" traits that fuel courageous leadership (and how to keep them from derailing you)

·       How two Threes with different subtypes actually make the perfect team

·       Jenny's raw reflections on control, comparison, and rediscovering what "enough" really means

·       The second half of life — and why it's less about achievement and more about awakening

It's an episode packed with laughter, candor, and the kind of vulnerability that reminds us: success without self-awareness isn't success at all.

🎙️ Listen in and learn how to move from human doing to human being — with a dash of wild courage.