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 throug...

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...

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 Rig...

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 Si...

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 communicati...

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 s...

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, t...

"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...

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...

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...

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 w...

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...

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...

  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 react...

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,...

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...

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 underst...

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-o...

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...

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 b...

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 inte...

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...

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 wh...

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 experi...

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 fo...