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

 

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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.


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Communication, Leadership, Relationships, Type 3Ian Cronenneagram, Relationships, business, Leadership, Communication