Fitting In vs. Belonging: What Enneagram Nines (and the Rest of Us) Get Wrong About Connection, with Brian Boecker
Typology
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 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...
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The Buddhist Enneagram: How Mindfulness Transforms Your Personality Patterns with Susan Piver
Typology
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...
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Courageous Conversations: How to Say What Needs to Be Said – Without Blowing It Up
Typology
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...
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Courageous Conversations: How Your Conflict Style Shapes Every Difficult Conversation
Typology
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...
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Courageous Conversations: Why We Struggle to Ask for What We Want (and How to Change It) with Attia Qureshi
Typology
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”...
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Courageous Conversations: The Inner Work that Builds Confidence
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 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...
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Replay: When the Life You Built Breaks Open w/Jen Hatmaker
Typology
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...
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Feeling Different? A Deep Dive into the Enneagram 4 Experience with Dudley Delffs
Typology
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...
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How the Enneagram Transforms Leadership and Workplace Culture
Typology
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...
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Part 2: The Enneagram in Therapy (What It Looks Like in the Room)
Typology
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...
info_outlineIn 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:
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the habits that no longer serve him
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the tender emergence of compassion
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learning to sit with grief rather than outrun it
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the uncomfortable art of slowing down
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how filmmaking and teaching have reshaped his inner life
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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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