Typology

  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...

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 spiritua...

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 emot...

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...

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...

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 H...

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 explorat...

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. T...

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,...

In this week's episode of Typology , I sit down with my dear friend and fellow book lover Joel Miller—an Enneagram Five through and through, and author of The Idea Machine: How Books Built Our World and Shape Our Future . Joel embodies the mind of a Five: curious, analytical, fiercely independent, and endlessly fascinated with ideas. But as we explore in our conversation, that intellectual brillia...

On this week's episode of  Typology , I'm joined by two remarkable guests who sit right at the intersection of faith and psychology: Dr. Les Parrott, a clinical psychologist and author, and pastor Judah Smith, who brings a preacher's honesty and a comedian's timing to our conversation. Together, they've written a new book called Bad Thoughts: A Preacher and a Shrink's Guide to Reclaiming Your Mind...

What if the real key to spiritual transformation isn't trying harder—but receiving love more deeply? In this heartfelt conversation, I sit down once again with Drs. Bill and Kristi Gaultiere—spiritual directors, therapists, and founders of Soul Shepherding—to explore what it means to truly receive and reflect God's empathy. Drawing from their new book, Deeply Loved , the Gaultieres invite us to co...

What is an Instinctual Stack? Do you know yours? We all have three instincts. None of us are absent one. However, one does tend to be dominant.  But what are instincts and how do they influence how each type shows up in the world?  In today's episode, we revisit our conversation with Elan Benami, creator of the EnneaApp and author of  Enneagram Patterns & Poetics, to provide you with a great overv...

What if the ways we keep getting stuck in relationships aren't just bad habits, but the natural outworking of how we're wired to bond—and to protect ourselves from pain? In this episode of Typology , I sit down with psychologist and couples counselor Dr. Lisa Marie Bobby (a freshly discovered Seven with an Eight wing) to talk about the intersection of attachment, addiction to love, and the Enneagr...