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.
ABOUT JENNY WOOD
Jenny Wood is the New York Times bestselling author of Wild Courage: Go After What You Want and Get It. In her book—and sought-after keynotes—she reveals nine unconventional traits that power the world’s most resilient and high-performing people.
A former Google executive and Harvard Business School researcher, Jenny spent 18 years rising from entry-level to COO roles across global divisions as the company scaled from 6,000 to 180,000 employees.
She led hybrid, multi-generational teams across the Americas, Asia, and Europe, helping drive billions in annual revenue while navigating hypergrowth, layoffs, and reinvention.
Despite never holding a formal People Operations role, Jenny founded Own Your Career, one of the largest internal career programs in Google’s history. The program reached 56,000 employees in nearly 100 countries—and redefined how Googlers build influence and grow their careers from day one.
Jenny has coached thousands of professionals and executives on leadership, resilience, teamwork, and influence. Her 375+ pieces on those topics, with features in Harvard Business Review, CNBC, Forbes, Business Insider, Entrepreneur, and Inc. Her dynamic keynotes blend bold storytelling, practical strategy, and real-world tools to help teams break the mold and lead with courage, and impact—especially under pressure. That’s why F500 companies like SalesForce, Oracle, Target, Capital One, Royal Caribbean, State Farm, CVS, and Johnson & Johnson invite her back to speak again and again.
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CONNECT WITH JENNY AND CARLINA
Jenny on Instagram
Jenny on LinkedIn
Jenny’s Website
Wild Courage: Go After What You Want and Get It
Carlina on LinkedIn
Carlina on Facebook