#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 Follow Rachel here:  https://www.instagram.com/ms_rach/ Follow Leo here: https://www.instagram.com/mr_agleooleo/ Discover ANON here: https://www.instagram.com/thehouseofanon/ Write in to the team at [email protected]