Typology

What does it mean to use the Enneagram in therapy responsibly? In Part 1 of this two-part conversation on Typology, Anthony Skinner and I lay the groundwork for therapists, counselors, and coaches who want to responsibly integrate the Enneagram into clinical practice with wisdom and care.  Together, we unpack what the Enneagram is—and what it isn't—in the therapy room. It's not a diagnosis. It's not a substitute for evidence-based modalities. And it should never flatten complexity or bypass deeper trauma work. I also share practical wisdom from decades of work as a thera...

There are conversations that stretch you a little. And then there are conversations that gently but firmly rearrange the furniture in your mind. This week, I sat down with Keith Kurlander and Will Van Derveer—co-founders of the Integrative Psychiatry Institute—to talk about something that's generating a lot of curiosity and, let's be honest, some anxiety: psychedelic-assisted therapy. Before you brace yourself, this isn't a hype session. It's a thoughtful, grounded conversation about trauma, the nervous system, and what happens when traditional therapy isn't enough to reach the deepest layers of pain we carry. <...

In this episode of Typology, I sit down with therapist and author Joe Nucci for a thoughtful, wide-ranging conversation about the Enneagram, mental health, and the growing misuse of therapeutic language in our culture. Joe—an Enneagram Three—shares his own journey with the Enneagram, the hidden shame dynamics of Threes, and how public success can quietly pull us toward performance instead of integrity. Together, we explore why tools like the Enneagram work best as maps, not MRIs—helpful for self-awareness and empathy, but dangerous when they turn into rigid labels. We also dig into Joe's...

What happens when Enneagram Eight energy grows up, softens its edges, and learns to lead with both strength and soul? In this episode of Typology, Ian Morgan Cron sits down with restaurateur, entrepreneur, and conscious capitalism advocate Dan Simons, co-owner of Founding Farmers, for a wide-ranging, deeply human conversation about power, protection, and what it really means to build a culture of care. Dan is brand-new to the Enneagram—and quickly discovers he's an Eight with a strong Nine wing, a compelling combination that blends moral clarity with empathy, decisiveness with nuance, and fire with ca...

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

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

What if your most meaningful work begins after you stop striving to prove yourself? In this warm, wide-ranging conversation, I sit down with old friend, songwriter, filmmaker, and Enneagram Two Andrew Greer for a heartful exploration of loneliness, love, boundaries, creativity, and what it really means to live a good life. Andrew opens up about the hidden sadness behind the Enneagram Two's gift for connection—the ache that often fuels the desire to help, anticipate, and care for others. Together, we unpack how pride, control, and fear of being a burden can quietly shape relationships, an...

This Christmas, we're delighted to bring back one of our most beloved conversations with Enneagram Three, pastor, and author AJ Sherrill. In this replay, AJ joins me to revisit the Nativity story—not as the sentimental tale we often breeze past each year, but as a rich, multilayered narrative pulsing with mystery, courage, vulnerability, and divine surprise. AJ shares his own journey into spiritual direction, what it's teaching him about listening, presence, and compassion, and how the Enneagram continues to shape his inner world. We explore why the season invites us to slow down, pay attention, and re...

With the holidays just around the corner, we're bringing back a conversation that continues to deliver relational gold. Whether you heard it the first time or you're discovering it now, this replay with author and Enneagram teacher Christina Wilcox offers a beautifully practical and deeply compassionate look at how the Enneagram can transform the way we show up for one another during the most emotionally charged season of the year. In this episode, Christina shares her journey of discovering herself as an Enneagram Six—along with the courage, clarity, and self-understanding that followed. Together, we explore how ea...

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...

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 pe...

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 st...

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: T...

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 lif...

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...

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 brilliance can also become a refuge—a way to manage anxiety, avoid dependence, and retreat from life itself. Together, we unpack what it means for Fives to move from "information to intimacy," from...

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 and Soul. It's a lively and deeply honest dialogue between theology and therapy—between the pulpit and the couch. We dive into what Les calls the five "toxic thought patterns" that...

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 consider a radical truth: that spiritual transformation begins not with striving or self-critique, but with allowing ourselves to be seen, known, and loved—just as we are. Together, we unpack how sham...

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 overview of Instincts, Subtypes, and the Instinctual Stack and how they can play out in your personal and professional life.    About Elan: El...

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 Enneagram. We explore why love itself can feel addictive, how that longing for connection sometimes binds us to the wrong person or pattern, and why recovery communities often wo...