Awakening in the Second Half: Jen Hatmaker on Loss, Love, and Letting Go

Typology

Ian Morgan Cron

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4.6 • 3.2K Ratings

🗓️ 11 December 2025

⏱️ 53 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 betrayal,
to leaving behind scripts you never chose,
to freedom from needing to be liked,
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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Transcript

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0:00.0	Hey folks and welcome to Typology, the show on which we explore the mystery of the human personality
0:08.7	and the great human adventure all through the lens of the Enneagram. My name is Anthony Skinner,
0:14.1	your producer and co-host. So glad you're here today, folks. Listen, today we're joined by
0:19.9	bestselling author, award-winning
0:22.0	podcaster, and someone who has lived her life in full view of the world with grit, humor,
0:27.4	and a whole lot of heart. We're talking about Jen Hatmaker, New York Times bestselling author,
0:32.8	a host of the widely beloved For the Love podcast. Her new memoir, Awake, is her bravest work yet
0:39.8	chronicling the shock, grief, and unexpected rebirth of midlife. Jen brings the love and the heat
0:46.6	today to the show. So glad you're here. Hey, that's it for me, Anthony Skinner. And now without any
0:52.3	further ado, here's the man of the hour, Ian Kron.
1:01.5	Hey, typology friends. Welcome back. Today's a big one, bigger than normal. In the house,
1:07.2	we have our good friend, author of the new memoir awake aneogram three the inimitable
1:14.6	the incomparable the the amazing jenn hadmaker welcome to typology that's a lot that's a lot first of all
1:25.6	well he ends a lot, so.
1:28.1	That's right.
1:29.0	That's fair.
1:31.0	We're just speaking truth here on typology podcast.
1:36.0	I'm happy to see you guys.
1:37.6	I'm so happy to be here.
1:39.4	I am so stoked to talk to you specifically about the new book awake, but I have a whole host of
1:46.8	anagram-related questions.
1:49.8	And so the book, the book begins with this horrible revelation that occurs some years ago, and you wake up at 2.30 in the morning to hear
	...

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