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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 Guilt Kept Me Quiet
A single choice to stay quiet can feel like self-protection…until it builds a wall you never meant to raise.
In this episode, I share a story about leaving a role I loved and telling a boss, who was also a friend, far too late. The career move was right. The offer made sense. But the harder lesson lived in what I didn’t say soon enough, and how that silence reshaped a relationship I cared about.
We’ll explore why “just what the contract requires” isn’t the whole picture when trust is involved, and how guilt and timing can quietly turn into distance. I reflect on the look that said, “I would have helped you,” and the irony that the support I needed was already there, but my own fear kept me from asking.
If you’ve ever replayed the conversation you didn’t have soon enough, this one will sit with you. Off My Chest is a space to let awkward, unfinished talks breathe—because once we name them, they start to loosen their grip.
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.
I still think about a silence I chose many years ago. Not in a meeting, not even an argument, but the moment I told my boss, who was also a good friend of mine, that I was leaving the organization. By then I had already wrestled with it for weeks. I had an offer in hand. I knew it was the right next move for me, and yet I hadn't said one word to her. We had worked side by side through really late nights, some really significant projects, and through a lot of constant change. I know she trusted me. I certainly trusted her. And still I kept quiet. And when I finally spoke, it was just when I had to give two weeks' notice. And the look on her face told me everything. It wasn't anger, it wasn't betrayal, just disappointment. And it was the kind of disappointment that said, I would have helped you, I would have been there for you if only you had trusted me enough to tell me sooner. Welcome to Off My Chest. I'm Anitra St. Hilaire. I have spent my career leading people and coaching executives. And if there's one thing I've learned, it's this conversations shape everything. Our work, our relationships, even how we see ourselves. But I'm not just here as a coach and a leader. I am here as someone who still replays her own awkward, painful, unfinished conversations. And that's what this podcast is all about. So back to my story. I want to be clear. I wasn't out there job hunting. I wasn't secretly scrolling job boards late at night. I had just randomly come across this opportunity. It was rare. It was a perfect fit from a company I was really excited about. And I knew I had to go after it. And I've always told people companies should be prepared. No one owes notice beyond what's in their contract. Of course, telling people you're leaving with extra time is helpful, can be very respectful. But at the end of the day, my counsel is always you have to do what's best for you. And that's the professional answer. But the personal side of me knew this silence came at a cost, and not just for the company I was working with, but for my boss, who I cared about. And I carried that guilt about making that decision much longer than the decision itself. Every day that passed without saying something made it so much harder to open my mouth. And the irony of this is I knew she would have supported me. I knew she would have worked with me through the transition. She would have given me a great recommendation to the company that I was going to look at. That's just who she was. And that's who we were as a team. That's who we were together. But I let myself get into this guilt spiral and I felt so poorly and so badly. And am I leaving this person in a bad position until it was just too late? And so when finally came down to it, and I had to tell her I was leaving, it landed not as a choice we could have navigated together, but really as a wall between us. And, you know, my not telling her, my silence really had already done its damage. And I still think about that to this day. I know leaving was the right decision, but not being honest earlier, hiding behind that guilt and letting that guilty feeling drive that silence is really the part of it I regret. And, you know, silence can feel like self-protection in the moment. But afterwards, it plays in your mind like an old record that you don't want to hear anymore. It's the distance that you've now created from people who really would have understood. It's the distance from the support that was actually there and that I knew was there, but just couldn't bring myself to ask for. And listen, the professional lesson is easy to name. Timing matters when you're leaving a job. Be clear, be honest, uh, tell the company when you need to, not a moment before. All of that is easy for me to rattle off. But the personal lesson, and it's really the hard one for me, is that sometimes silence can cost you closeness with someone you care about. And the people you work with aren't necessarily one and the same with the company you work with. And once that distance is there, it's really hard to bridge. And so if I had to do it all over again, I would probably tell her a little sooner. I can't say that I would, though, because I was I was nervous and uncomfortable and younger and didn't have all the confidence that I have now and really worried about what would happen to me. And, you know, it's all it's all dependent on who you are in your particular situation. But I really just wanted to take a moment and reflect that this one felt bad because I did treat her not as a friend, and I knew she was. And not everyone you work with is your friend, but in this case, she was mine, and I should have I should have treated her like the friend she was to me. And that's what this space is for. It's a place to bring those messy conversations into the light and see what happens when we stop carrying them alone. Each week I'll share more stories, sometimes mine, sometimes from guests that just name conversations we can't shake. Because once we name them, they start to loosen their grip. So thanks for listening, and thank you for letting me get this off my chest.