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Our friend Jeff Cook—writer, podcaster, and Enneagram systems thinker—is back with us to discuss his recent book (volume 1 of a series because of course it is): about the Enneagram. (See our first conversation from S03E26 here.)

Jeff explains how the Enneagram names the “why” beneath our choices, conflicts, faith, and love. Randy shares how the framework has sharpened his self-awareness and softened his edges. And Kyle characteristically pushes back a bit on evidence, parsimony, and the risk of thick theories outrunning data. The result is a lively, generous exploration that treats the Enneagram as a language for motive rather than a box for behavior.

Jeff starts by laying a foundation—head, heart, and body—as an ancient scaffold echoed in philosophy, spirituality, and clinical practice. From there, he maps how core desires show up under stress and security and why the hardest question, “What do you want?”, may be the doorway to identity and change. We pressure-test the model where it matters most: relationships. Randy gets a live read on Eight-with-Six dynamics—strength meeting vigilance, autonomy meeting reassurance—and why "body types" experience control and agency in ways that feel physical, not theoretical. We also tackle the cottage-industry problem, academic standards, and how to treat the Enneagram like a Wittgensteinian ladder: use it when it helps, set it aside when it doesn’t.

If you’ve been burned by rigid labels, you’ll appreciate our insistence on flexibility, nuance, and practical outcomes. If you’re curious about real-life gains, Jeff’s focus on gifts will resonate: name what you uniquely bring—clarity, courage, steadiness, empathy—and aim it outward. Useful, not ultimate. Humble, not hazy.

Enjoy the conversation? Subscribe, share with a friend who loves a good debate, and leave a review on Apple or Spotify.

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