About this episode
In today's conversation, I sit down with Ian Cron — a psychotherapist, priest, bestselling author of The Road Back to You, and one of the world's leading experts on the Enneagram. This episode hit me far harder than I expected. Ian doesn't just explain the Enneagram… he helps us understand how our personality type shapes our marriage, our parenting, our leadership, and even the stories we tell ourselves. But things get incredibly real when Ian puts me through a live guided inner-work exercise. Within minutes, he led me straight into one of the deepest beliefs I carry about success, provision, and worth — taking me face-to-face with the 12-year-old version of myself who still drives far more than I realized. It was raw, vulnerable, uncomfortable… and one of the most powerful moments I've had behind this microphone. If you've ever wondered why you do what you do, why you push so hard, or why your strengths sometimes undermine you, this conversation will stop you in your tracks. Timeline Summary: [0:00] – Introducing the episode and why today's conversation hit harder than expected. [1:27] – Ian Cron's background as a psychotherapist, priest, and Enneagram expert. [2:12] – Ian explains the nine personality types in plain language. [2:42] – Why I chose to get vulnerable and let Ian guide me through inner work. [3:25] – A moment of intense authenticity as I sit face-to-face with my younger self. [11:51] – Nature vs. nurture — where personality comes from. [13:34] – Why self-awareness is essential for good living, marriage, and parenting. [15:31] – Applying Enneagram wisdom to understanding kids and their inner worlds. [17:22] – How knowing my wife's type changed our marriage. [18:27] – "What's best about you is also what's worst about you." [19:59] – Ian analyzes my type (3w2) and explains why he knew so much about me instantly. [21:42] – How threes may unintentionally run over people while chasing goals. [22:50] – Parenting kids who aren't wired like you — and avoiding making them copies. [24:12] – Why every type has strengths, weaknesses, and a path toward health. [26:32] – Understanding your kids' Enneagram types and customizing your parenting. [27:48] – When kids should take the Enneagram test. [29:03] – My own reflections on turning 50 and becoming more self-aware. [30:19] – How to begin inner work and understand your type's shadow side. [31:21] – The shift from first-half-of-life achievement to second-half-of-life meaning. [32:36] – Do Enneagram types change over time? [33:58
