#49: Leo: "The Most Humbling Season Of My Life"

Over the past year, I’ve watched Leo move through what he describes as one of the most humbling seasons of his life.

In this conversation, he reflects openly on what it has meant to start again, to build from scratch, and to remain teachable after years of experience. He speaks honestly about doubt, ego, frustration, and the courage it takes to stay with the work when things feel uncertain.

What made this conversation especially meaningful for me was how deeply moved I was by his honesty.. watching him name his struggles, sit with discomfort, and keep choosing growth in real time.

This is a story of growth in progress; honest, unfinished, and grounded in real life.

Chapters

• 00:00:00 A Year of Reflection with Leo
• 00:02:14 Fatherhood, Presence, and Breaking Old Patterns
• 00:06:21 Finding Joy Again Through Cooking and Showing Up Consistently
• 00:07:58 Starting Over at 52: Building Something New from Scratch
• 00:12:02 Marriage Under Pressure and Choosing to Stay
• 00:14:00 Learning to Stay Open During Hard Conversations
• 00:17:01 Letting Go of Ego and the Need for Control
• 00:20:58 Becoming More Open and Staying Teachable
• 00:28:24 When Self-Worth Is Shaken and Slowly Rebuilt
• 00:31:16 Closing Reflections

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