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Off My Chest - Conversations We Can't Stop Replaying
We’ve all had conversations that won’t leave us alone. The ones we wish had gone differently. The ones that left us second-guessing. Off My Chest is about those messy, unfinished moments.
Each week, host Anitra St. Hilaire shares stories about the conversations that still linger. Sometimes it’s the one you wish you’d handled differently. Sometimes it’s the silence when you froze instead of speaking up. Sometimes it's someone who just treated you poorly.
Unlike many relationship podcasts, this isn’t therapy, advice, or gossip. It’s short, intimate storytelling that offers recognition (I’ve been there too), reflection (why do I carry this?), and release (maybe I don’t have to anymore).
The goal isn’t to fix the past, but to name it, share it, and let some of the weight go.
Off My Chest - Conversations We Can't Stop Replaying
When O Means Outstanding: Rethinking Assumptions, Power, and Listening
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.
Picture this. I come home from school clutching my report card. Proud, excited. I'd worked hard and it showed. I had O's across the page. O for outstanding. I ran straight to my parents' room to show them. My father was there. Gave him that report card. He glanced down, saw those O's, and his face completely hardened. You got zeros, he told me. How on earth did you fail all of your classes? Welcome to Off My Chess, the podcast about the conversations we can't stop replaying, the ones we wish had gone differently, or that still sort of weigh on us. I'm Anitra St. Hilaire. I have spent my entire career leading people and coaching executives. And if there is one thing I've learned, it's this. Conversations shape everything, our work, our relationships, and even how we see ourselves. But I'm not here just as a coach and leader. I'm here as someone who still replays her own awkward, painful, unfinished conversations. And that's what this podcast is all about. So I can still see it. My parents' bedroom, my dad in bed. He spent a lot of time there as his health had begun to decline at this point. He was dying of Lou Gehrig's disease, ALS. And so I just remember coming into that space and me standing there with my head down, clutching that piece of paper. And to be fair, my dad was not in his best state of mind most of the time back then. In addition to just being sick and knowing he was going to die, he really struggled with alcohol. And I believe that that shaped how he reacted to me in that moment. But the paper itself was they have this visceral memory of it being soft and a little bit damp from me, clutching it in my hand as I had walked home with it. And in that moment, it could have been cactus needles. It was just so uncomfortable. And I think so much of that was my expectation. I expected celebration, a smile, maybe a job well done. But instead I got real suspicion and anger, an anger that seemed to come out of nowhere from him. And it felt like my stomach dropped to the floor, the way you might feel when you're scared. And I tried to explain. I pointed to the report guard and said, no, no, no. See, O is for outstanding. They have a different rating scale. O is outstanding, E is excellent. It wasn't your standard A, B, C, D, F sort of scale. And I remember trying to explain, like, you know, I'm a good student. Look at the notes. My teacher had written positive notes about me. And everything on that piece of paper proved what I knew to be true, that I had done well this semester. But he wouldn't have any of it. He doubled down. And I remember him saying, I'm not stupid. I know a zero when I see one. And you haven't been doing your work. And yeah, at first I was really confused because I just didn't understand how he couldn't see what was right there in front of him. And my tears started to come and my throat was burning. And I just kept trying to explain the words getting caught in my throat somewhere between anger and confusion and disappointment and sadness. And for a moment, the confusion really did give way to doubt. Like, did I get something wrong here? Did I misread something? And tears came, but I didn't really get angry, at least externally at him, because honestly, as a child, I wasn't allowed to be angry at my father. And so eventually I just gave up. I walked away. I went into my room, report card in hand, and I remember putting it down and just rubbing the creases out of it, as if somehow smoothing the creases and making the paper flat could make the whole thing make sense. And listen, whether he later figured it out, which he probably did, whether he apologized, which, if I'm honest, he probably didn't, it doesn't really matter. What stayed with me wasn't even the grade. It was just that moment of excitement and knowing I was right and I had evidence, but still not being believed. And my father has long, long passed, and so this is never a conversation that I'm gonna get closure on or revisit. But really, when I think about that moment, the lesson for me isn't isn't about truth, though there is something around knowing what I know to be true and not letting someone take that away from me. But it's about expectations and the danger of someone jumping to conclusions without really understanding. And so many years later, my kids have this thing called competency-based learning, which is a grading system with no letters at all. And I remember this old memory coming up as I thought about, you know, what my kids' quote unquote grades were going to be and knowing they weren't going to have grades in the standard way that I remember grades. And instead of assuming I knew what everything meant, I really dug in to understand what the company Bain's learning system was about because I wanted to understand it well enough to celebrate them properly and to know when there was a problem and to not just assume I knew the truth. And truly, listen, the report card isn't the be-all end all, but I I knew that if I understood what their report cards looked like and what they were supposed to measure, and if those didn't reflect what I knew to be true about my kids, then my first step wouldn't be to assume the school was right or that my kids were wrong. It would be to ask questions. It would be to gather more information and make sure I was operating with a somewhat full set of information, unlike what my father did. And that's that's the shift in the learning for me. Where my father left absolutely no room for him to be wrong, uh, I try to leave space. Space for a difference in understanding, space for curiosity before judgment. And listen, we all know sometimes authority does have the final say, but the people closest to the work, or in my case, closest to the experience of being a student in school, almost always know something we don't. And honestly, that's why if you're in a position of power, make sure you leave room to be wrong. That single habit, that single piece of advice, leaving space to be wrong will earn you so much more credibility than pretending you always know best. Because honestly, that cost isn't just credibility, but when authority, when power shuts down curiosity, the whole system suffers. People stop speaking up, innovation dries up, and the best ideas just never come to light because there isn't space to have your mind changed. And I've seen this in leadership all the time, where executives make a call without listening to the people doing the work. And nine times out of 10, that decision costs more time, more money, and more trust than if we had just pause to listen, to be curious, and to have a chance at having our minds changed. And if we don't take the time to listen, we miss it. And that's just not a small mistake. That is a huge miss for everyone. And that's what this space is for: a place to bring those messy conversations into the light and see what happens when we stop carrying them alone. So each week I will share more stories, sometimes mine, sometimes from some guests. And we're gonna name the conversations we can't shake because once we name them, they start to loosen their grip on us a little bit. So thank you for listening and thanks for letting me get this off my chest.