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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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A single letter changed everything. I brought home a report card full of “O’s” for Outstanding and watched my dad read them as zeros. That moment became a lifelong lesson about assumptions, authority, and what happens when certainty replaces curiosity.
In this episode, I revisit that scene, a bedroom shadowed by illness and alcohol, and trace how misread signals shape the way we parent, lead, and listen. We talk about leaving room to be wrong, asking what a metric truly measures, and why credibility grows from course correction, not perfection.
If you’ve ever felt unseen or unheard, this one’s for you.
Off My Chest is created and hosted by Anitra St. Hilaire. If you'd like to hear more from me, sign up for my newsletter, Mirror Truth.
Chapters
1. When O Means Outstanding: Rethinking Assumptions, Power, and Listening (00:00:00)
2. The Report Card Misread (00:00:03)
3. Show Introduction & Host Context (00:00:40)
4. Father’s Health and State of Mind (00:01:18)
5. The Clash Over “O for Outstanding” (00:02:26)
6. Aftermath: Doubt, Silence, and Resignation (00:04:22)
7. From Memory to Meaning: Expectations (00:04:51)
8. Parenting With Curiosity Over Certainty (00:05:44)
9. Leadership Lesson: Leave Room to Be Wrong (00:06:49)
10. Why Curiosity Protects Trust and Innovation (00:08:16)
11. Closing: Naming Conversations to Loosen Their Grip (00:08:48)
3 episodes
