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...
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The Enneagram in Therapy (Part 1): How to Use It With Care, Clarity, and Clinical Wisdom
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 therapist,...
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The Future of Mental Health: Psychedelics, Trauma Recovery, and the Enneagram
Typology
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...
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When Therapy Speak Goes Too Far, with Joe Nucci
Typology
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...
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The Defender’s Way: How Enneagram Eights Can Build Cultures of Care Without Losing Power”
Typology
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...
info_outlineWhat 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:
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to grief and betrayal,
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to shedding scripts you never consciously chose,
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to loosening your grip on approval,
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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.