Midlife shift: first to second half

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] – Ian shares the hard truths about being a Type 4 and the work it required.

[35:51] – What makes the Enneagram "painfully accurate" — and why it stings at first.

[43:03] – Why dating app "compatibility" algorithms may be misleading.

[46:16] – The danger of being married to someone exactly like you.

[47:15] – Why I talk to the "achiever" part of myself and how Ian explains this phenomenon.

[49:21] – Understanding internal "parts" and learning to lead them well.

[52:06] – The moment my 12-year-old self emerges during the guided exercise.

[1:02:14] – Why self-knowledge is the beginning of wisdom.

[1:03:27] – Ian's resources: assessments, coaching, books, and his Typology podcast.

[1:04:45] – Final reflections and directing listeners to the show notes.

Five Key Takeaways

1. The Enneagram reveals core motivations, not just behaviors. Understanding your type gives you a mirror into why you act, think, and feel the way you do.
2. Self-awareness is foundational to healthy marriage and parenting. When you understand your patterns, blind spots, and triggers, you show up more intentionally for the people you love.
3. Your strengths also contain your shadow. "What's best about you is also what's worst about you" — and growth requires facing both sides honestly.
4. Inner-work exposes old parts still running your life. The guided exercise revealed a wounded 12-year-old part of me still driving my need to achieve and provide.
5. Your type doesn't change, but you evolve within it. True maturity comes from learning to lead your personality, not letting it lead you.

Links & Resources:

• Ian's website & resources: https://www.ianmorgancron.com
• Ian's book: The Road Back to You: https://www.amazon.com/Road-Back-You-Enneagram-Self-Discovery/dp/0830846190
• Bark x The Dad Edge: http://thedadedge.com/bark
• Show notes: https://thedadedge.com/1410

Closing Remark

If this episode gave you a moment of clarity, helped you understand yourself better, or challenged you to grow, please rate, review, follow, and share the podcast. From my heart to yours, thank you for listening — now go out and live legendary.