Awakening in the Second Half: Jen Hatmaker on Loss, Love, and Letting Go
Release Date: 12/11/2025
Rediscover the Christmas Story You Thought You Knew, with AJ Sherrill (Replay)
Typology
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...
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Caring for Every Type at Christmas: A Holiday Conversation with Christina Wilcox (Replay)
Typology
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...
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Awakening in the Second Half: Jen Hatmaker on Loss, Love, and Letting Go
Typology
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 and...
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Lynn Smith on Leadership Confidence and Overcoming the Brain Bully (Enneagram 3)
Typology
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...
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Gratitude for each Enneagram Type
Typology
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...
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The Sacred Ache and Beauty of Becoming with Heath Hardesty
Typology
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 . 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: The difference between helping and hiding Why our “ache” might actually be a form of divine homesickness How beauty, poetry, and the transcendent...
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Steve Taylor on Maturity, Mindfulness & Meaning (Enneagram 7)
Typology
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...
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Wild Courage and the Heart of the Enneagram Three, with Jenny Wood and Carlina Daugherty
Typology
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...
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Joel Miller on the Inner World of the Enneagram Five and the Power of Ideas
Typology
), a popular Substack celebrating literary culture. He is the author of several books, including (forthcoming, November 2025). His writing has appeared in Reason, the Washington Post, American Spectator, and National Review. He lives outside Nashville, Tennessee, with his wife, kids, dogs, and more books than space. Available now for pre-order: Follow on Apple Podcast, Spotify, or your favorite podcast player to learn more about the Enneagram and personal growth.
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Bad Thoughts: When a Preacher and a Shrink Team Up to Heal the Mind and Soul, with Judah Smith and Dr. Les Parrott and
Typology
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 . 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 keep us stuck—guilt, shame, insecurity, entitlement, and...
info_outlineWhat 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:
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to grief and betrayal,
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to leaving behind scripts you never chose,
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to freedom from needing to be liked,
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to discovering what really matters in the “second half of life.”
We dive into the Enneagram and the unique way Threes navigate identity, image, success, and failure—especially when life doesn’t cooperate with the plan. Jen shares how therapy, embodiment work, and raw honesty helped her rebuild, and why this memoir isn’t about spectacle, but about hope.
This is a conversation about midlife transition, spiritual awakening, and the quiet miracle of becoming more fully yourself—right when you thought everything was falling apart.
If you’re navigating change, heartbreak, faith shifts, or a midlife renaissance of your own, this episode will feel like a hand on your shoulder and a light on the path.
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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.
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