Court-side Conversations with Courtney

Courtney Headley
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Court-side Conversations: Bold women. Strong voices. Real talk.Court-side Conversations 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 when navigating the workplace feels isolating, it helps to hear from someone who’s 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.

Episodes

  1. Jul 18

    Learning as You Go: Intuition, Mentors & Entrepreneurship | Maggie Williams

    What if you didn't have to have everything figured out before taking the next step? In this episode of Court-side Conversations, Courtney Headley sits down with entrepreneur and commercial real estate professional Maggie Williams to explore what she's learned from building an unconventional career, investing in opportunities before she felt completely ready, and navigating entrepreneurship one step at a time. Maggie shares why she believes the best opportunities often come from learning as you go, trusting your intuition when things don't feel right, and surrounding yourself with people who can help you grow instead of trying to have all the answers yourself. Together they discuss: • Why taking action often matters more than having the perfect plan • The career lesson behind "Who, Not How" • How mentors and masterminds can accelerate your growth • Learning to trust your intuition when self-doubt shows up • Why optimism can be a competitive advantage in entrepreneurship If you've ever felt like you needed to have everything figured out before moving forward, this conversation will remind you that confidence is often built by taking the next step...not by waiting for certainty. Pull up a chair, grab a drink, and join us Court-side. Connect with Courtney 💛 LinkedIn: www.linkedin.com/in/courtneycheadley 💛 Learn more about Center Court Collective 🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial About the Podcast Court-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.

    Learning as You Go: Intuition, Mentors & Entrepreneurship | Maggie Williams

  2. Jul 4

    When Everyone Starts Looking to You for Answers | Kate Coelho

    There comes a moment in your career when something shifts without you noticing. One day you're the person asking the questions. The next, everyone is looking to you for the answers. And for many women, that's exactly when self-doubt gets the loudest. In this conversation, Kate Coelho shares what it was like navigating that transition, why advocating for yourself matters just as much as doing great work, and how she's learned to trust herself even when her inner critic shows up. We also talk about:  • Why "keep your head down and work hard" isn't enough  • The importance of advocating for yourself  • Balancing leadership, motherhood, and life outside of work  • Why growth and discomfort almost always arrive together If you've ever wondered whether you deserve your seat at the table, this conversation is for you. Pull up a chair, grab a drink, and join us Court-side. Connect with Courtney 💛 LinkedIn: www.linkedin.com/in/courtneycheadley 💛 Learn more about Center Court Collective 🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial About the Podcast Court-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.

    When Everyone Starts Looking to You for Answers | Kate Coelho

  3. Jun 20

    Know Your Strengths, Trust Yourself More | Jocelyn Guite

    What if the key to moving through self-doubt isn't fixing your weaknesses, but better understanding your strengths? In this episode of Court-side Conversations, I sit down with my longtime friend Jocelyn, an HR leader with more than 15 years of experience across multiple industries. We talk about: How Clifton Strengths changed the way she views herself and others Why asking for help is a strength, not a weakness The role self-doubt played when she first became a manager How she learned to leverage her natural talents instead of fighting against them Recognizing when it's time to leave a manager or environment that no longer serves you Plus, you'll hear a few unexpected leadership lessons from Pitbull.  If you've ever questioned whether you're qualified, capable, or ready, this conversation is a reminder that you may already have more than you think. Pull up a chair, grab a drink, and join us Court-side. Connect with Courtney 💛 LinkedIn: www.linkedin.com/in/courtneycheadley 💛 Learn more about Center Court Collective 🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial About the Podcast Court-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.

    Know Your Strengths, Trust Yourself More | Jocelyn Guite

  4. Jun 5

    She Looked Confident. She Was Secretly Second-Guessing Everything. | Angelique Bui

    What if the people who seem the most confident are also questioning themselves behind the scenes? In this episode of Court-side Conversations, Courtney sits down with Angelique Bui, a leader with more than 30 years of experience in corporate America, to talk about the self-doubt that followed her throughout her career, even when others saw her as confident, capable, and strong. Angie shares what it was like leaving a company after 17 years, stepping into a completely new role, navigating intense imposter syndrome, and learning how to move forward anyway. Together, Courtney and Angie explore: • What imposter syndrome feels like • The power of self-affirmation during moments of uncertainty • Why learning to lead without authority matters • How to quiet the noise when your inner critic gets loud • Why giving yourself permission to make mistakes is so important If you've ever looked successful on the outside while quietly questioning yourself on the inside, this conversation is for you. Pull up a chair, grab a drink, and join us Court-side. Connect with Courtney 💛 LinkedIn: www.linkedin.com/in/courtneycheadley 💛 Learn more about Center Court Collective 🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial About the Podcast Court-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.

    She Looked Confident. She Was Secretly Second-Guessing Everything. | Angelique Bui

  5. May 22

    Finding Joy in Everyday Life | Jamie King

    What happens when you stop trying to be perfect and start trusting yourself a little more every day? In this episode of Court-side Conversations, Courtney sits down with one of her closest friends, Jamie King, for an honest conversation about career growth, self-doubt, motherhood, stress, confidence, and finding joy in the middle of real life. Jamie shares what it looked like to leave a job without a plan, return to a workplace that truly felt like home, navigate leadership in male-dominated industries, and push herself through fears like public speaking. This conversation is full of practical wisdom, humanity, laughter, and reminders that growth doesn’t always look polished. Sometimes it looks like standing up in meetings just to prove to yourself you can. 💛 In this episode, we talk about:  Finding joy in everyday moments  Building confidence over time  Public speaking fears and how to move through them  The power of supportive friendships and community If you’ve been searching for a little bit more joy in your life…this one is for you.  Pull up a chair, grab a drink, and join us Court-side. About the Podcast Court-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.

    Finding Joy in Everyday Life | Jamie King

  6. May 8

    Choose Your Pain: Trusting Yourself Instead of Playing the Game | Marlenne Johnson

    This episode is for the woman who feels like she has to change who she is to succeed. I’m joined by Marlenne Johnson, someone I’ve known for years and deeply admire for her honesty and self-awareness. We talk about what it actually looks like to navigate environments where you don’t feel like you belong… and the choice so many women face: Do I play along…or stay true to myself? Marlenne shares her journey through HR, from trying to fit into a male-dominated environment to making conscious decisions about who she wanted to be, even when it was uncomfortable. This conversation is honest, grounding, and a reminder that:  You’re not for everyone…and that’s okay  Self-doubt doesn’t mean you’re doing it wrong  Community matters more than we think  And sometimes the real work is choosing yourself, over and over again If you’ve been second-guessing yourself or wondering if you need to be different to move forward…this one is for you. 💛 Pull up a chair, grab a drink, and join us Court-side. About the Podcast Court-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.

    Choose Your Pain: Trusting Yourself Instead of Playing the Game | Marlenne Johnson

  7. Apr 24

    Get Out of Your Head and Trust What You Feel | Ashley Watkins

    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 Podcast Court-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.

    Get Out of Your Head and Trust What You Feel | Ashley Watkins

  8. Apr 11

    If You’re Not Growing, You’re Rotting | Allison “Allie” Germain

    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 Podcast Court-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.

    If You’re Not Growing, You’re Rotting | Allison “Allie” Germain

  9. Mar 27

    When Everything Feels Split | Jessica Johns

    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 Podcast Court-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.

    When Everything Feels Split | Jessica Johns

  10. Mar 13

    A Conversation with My Mom | Chris Johnson

    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 Podcast Court-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.

    A Conversation with My Mom | Chris Johnson

  11. Trailer

    Trailer: Welcome to Court-side Conversations with Courtney

    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.

Trailer

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About

Court-side Conversations: Bold women. Strong voices. Real talk.Court-side Conversations 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 when navigating the workplace feels isolating, it helps to hear from someone who’s 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.

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