Wild Courage and the Heart of the Enneagram Three, with Jenny Wood and Carlina Daugherty

Typology

Ian Morgan Cron

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4.6 • 3.2K Ratings

🗓️ 6 November 2025

⏱️ 64 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 that fuel courageous leadership (and how to keep them from derailing you)

· How two Threes with different subtypes actually make the perfect team

· Jenny's raw reflections on control, comparison, and rediscovering what "enough" really means

· The second half of life — and why it's less about achievement and more about awakening

It's an episode packed with laughter, candor, and the kind of vulnerability that reminds us: success without self-awareness isn't success at all.

🎙️ Listen in and learn how to move from human doing to human being — with a dash of wild courage.

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
0:08.8	personality and the great human adventure all through the lens of the Enneagram.
0:14.1	My name is Anthony Skinner, your producer and co-host. So happy to have you here today,
0:18.4	folks. Listen, we've got a really great interview today.
0:22.5	It's a powerful story.
0:24.7	It's something that I think if you get your hands on, it can be really helpful for all of you listening.
0:30.2	And an interesting story around this guest discovering her an egram type, some in real time with us today on the show. I'm talking
0:40.7	about Jenny Wood, a former Google executive leadership coach and New York Times bestselling author
0:46.8	of the brand new book, Wild Courage. Go after what you want and get it. I'm reading this book
0:52.0	right now, folks. In her book, Jenny shares nine
0:55.8	unconventional traits that power some of the world's most resilient and high-performing
1:00.8	people. Sounds like an Enneagram 3, right? Over her 18-year career at Google, she rose from
1:06.4	entry-level to C-O-O roles leading global teams across the Americas Asia and Europe, as the company
1:13.9	grew from 6,000 to 180,000 employees. Crazy amounts of growth. She gives these secrets away in her book now,
1:24.5	okay? Jenny also founded Own Your Career, one of Google's largest ever internal career programs.
1:31.1	She talks about this in the book, reaching more than 56,000 employees in nearly 100 countries.
1:36.2	Her thought leadership has been featured in Harvard Business Review, CNBC, Forbes Business Insider, Entrepreneur, and Inc. Also, really fun today, Jenny is joined by her
1:47.8	chief of staff and Enneagram practitioner, and she's helped Jenny prepare for this interview and
1:54.0	joins us as well as I've said, Carolina Doherty. So happy to have them both here. They're both
1:59.8	Enneagram 3s, super pumped to have them on the show. Today we talk about Jenny coming into the revelation that she is an aneagram 3. And what that means, we talk about the strengths of the three, the shadow of the three. And we talk about her brand new book, which again, as I said, I'm reading it, loving it.
2:18.8	You're going to love this interview, folks.
2:19.5	Glad you're here.
	...

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