Court-side Conversations with Courtney

If you’ve been living in your head… second-guessing, overthinking, trying to “figure it out”… this episode is for you.In this conversation, I’m joined by Ashley Watkins, a former teacher turned coach, who built her career not by following a plan… but by following what felt right.We talk about what it actually looks like to trust yourself in real life. Not in theory.Ashley shares how she makes decisions based on her gut, how her inner critic shows up as she builds her business, and why community has been one of the biggest shifts in quieting self-doubt.We also get into: The moment you know you’ve disconnected from your intuition  Why overthinking is often a sign you’re in your head, not your body  The pressure to “have a plan” and what happens when you don’t  The best and worst career advice she’s ever received  Why “have more fun” might be more important than you think This one is honest, grounded, and a reminder that you don’t need more strategy… you need to trust yourself enough to take the next step.Pull up a chair, grab a drink, and join us Court-side.About the PodcastCourt-side Conversations is a podcast about leadership, self-trust, and the moments that shape us.Each episode features a candid conversation with remarkable women about the experiences that helped them trust themselves, navigate challenges, and move forward with confidence and integrity.Hosted by Courtney Headley, founder of Center Court Collective.New episodes released every other week. 

This episode is for any woman who feels stuck… and knows something needs to change.In this conversation, I sit down with my friend Allison “Allie” Germain to talk about fear, growth, and what actually keeps us from taking the next step.We talk about: What it feels like to be in a role that doesn’t fit  The difference between comfort and growth  How fear shows up when you're thinking about change  Why overthinking keeps you stuck  And what it actually looks like to move forward anyway At one point, Allie shares a line that stuck with me:“If you’re not growing, you’re rotting.”It’s simple. And it’s honest.If you’ve been sitting in indecision, waiting to feel ready, or questioning whether you should make a move… this conversation will meet you right where you are.Pull up a chair, grab a drink, and join us Court-side.About the PodcastCourt-side Conversations is a podcast about leadership, self-trust, and the moments that shape us.Each episode features a candid conversation with remarkable women about the experiences that helped them trust themselves, navigate challenges, and move forward with confidence and integrity.Hosted by Courtney Headley, founder of Center Court Collective.New episodes released every other week. 

Some seasons of life don’t fit neatly into categories.You’re not all in at work.You’re not all in at home.And no matter what you choose, it can feel like something is getting less of you.In this episode, I sit down with one of my closest friends, Jessica Johns, to talk about what happens when your identity shifts, your priorities change, and the way you’ve always measured yourself no longer applies.We talk about: the tension of motherhood and career  learning to make decisions that don’t always make sense on paper  and what it looks like to trust yourself when there’s no clear right answer This one is especially for the moms.Pull up a chair, grab a drink, and join us Court-side.About the PodcastCourt-side Conversations is a podcast about leadership, self-trust, and the moments that shape us.Each episode features a candid conversation with remarkable women about the experiences that helped them trust themselves, navigate challenges, and move forward with confidence and integrity.Hosted by Courtney Headley, founder of Center Court Collective.New episodes released every other week. 

Some of the most meaningful insights in my life have come from simply sitting across the table from someone and asking a few thoughtful questions.For the first episode of Court-side Conversations, it felt only right to start with the woman who has had the greatest influence on my life, my mom, Chris Johnson.In this conversation, we talk about the moments that shape us, the quiet confidence that comes with experience, and the lessons that stay with us long after the moment has passed.Pull up a chair, grab a drink, and join us Court-side.About the PodcastCourt-side Conversations is a podcast about leadership, self-trust, and the moments that shape us.Each episode features a candid conversation with remarkable women about the experiences that helped them trust themselves, navigate challenges, and move forward with confidence and integrity.Hosted by Courtney Headley, founder of Center Court Collective.New episodes released every other week. 

Welcome to Court-side Conversations with Courtney.This podcast brings women together for honest conversations about work, confidence, and finding their voice without the corporate speak.Each episode centers on real stories, lessons learned, and the advice women embraced or intentionally left behind along the way.Because navigating the workplace can feel isolating sometimes. And it helps to hear from someone who has been there too.When women share their experiences openly, we learn faster, feel less alone, and lift each other up in the process.These conversations happen the way all good ones do. Over drinks. In good company.Pull up a chair and join me, Court-side.New episodes launch every other week.