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.

  1. Oct 27

    When Letting Go at Work Feels Like Failing | Jackie Hendy

    You’re delivering. Your team is delivering. So why does being asked to delegate feel like a sign you’re falling short? When Jackie Hendy’s CEO asked her to hire VPs, he wanted more time with her to think about the business and its strategy. She worried it meant she wasn’t performing. In this episode of Court-side Conversations, Jackie shares what she learned about self-doubt, belonging, and letting go throughout a career that took her from receptionist to Chief Human Resources Officer. From feeling welcomed in a male-dominated fire service to feeling unheard at the executive table, Jackie reflects on what helped her contribute, trust her experience, and stay true to herself. We talk about: • Why accomplished leaders still question themselves • The difference between being included and feeling heard • Why she rejected advice to change her hair for an executive role • The advice that stayed with her after delivering a difficult layoff • Learning that delegating doesn’t diminish your value 💛 If this conversation resonates, share it with a woman you love. Follow Court-side Conversations for new episodes every other week. CONNECT WITH COURTNEY 💛 LinkedIn: https://www.linkedin.com/in/courtneycheadley/ 💛 Center Court Collective: https://www.centercourtcollective.com 💛 Join Center Court Connections: https://www.centercourtcollective.com/centercourtconnections 💛 Coaching, speaking, or podcast inquiries: courtney@centercourtcollective.com ABOUT THE PODCAST Court-side Conversations is a podcast about leadership, self-trust, and the moments that shape us. Hosted by Courtney Headley, career coach and founder of Center Court Collective, each episode features a candid conversation with a remarkable woman about navigating challenges and moving forward with confidence and integrity. #WomenInLeadership #SelfTrust #LeadershipConfidence #CourtsideConversations

    When Letting Go at Work Feels Like Failing | Jackie Hendy

  2. Oct 10

    Not Speaking Up Is a Career-Limiting Move | Yee May Leong

    What if NOT speaking up for yourself is the very thing holding your career back? Yee May Leong spent more than 40 years building a career in tech, often as the only woman in the room. Over the years she learned that advocating for what you believe in, even when it ruffles feathers, is essential to success. In this conversation, Yee May shares why finding sponsors matters, how she's learned to pick her battles, and why self-doubt can actually be a good thing. We also talk about belonging, being comfortable in your own skin, giving yourself grace, and remembering that your career is only one part of your life. Pull up a chair, grab a drink, and join us Court-side. If you enjoyed this conversation, share it with a woman you love. 💛 💛 Want more conversations like this? Join Center Court Connections for monthly ideas, stories, and questions to help you hear yourself more clearly and take your next step with confidence: Center Court Connections | Center Court Collective 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.  #WomenInLeadership #CareerGrowth #SelfTrust #SelfAdvocacy #CourtsideConversations

    Not Speaking Up Is a Career-Limiting Move | Yee May Leong

  3. Sep 26

    Be a Sponge: The Career Advice That Helped Fran Carasco Grow

    What if one of the best things you could do for your career was admit what you don’t know? Fran Carasco has built her career by staying curious, building relationships, and learning from the people around her. Her approach? Be a sponge. In this episode of Court-side Conversations, Fran shares why she believes your network is your net worth, why she intentionally does things that make her uncomfortable, and how being willing to say “I don’t understand” has helped her grow. She also gets candid about the self-doubt that still shows up along the way and the simple pen-to-paper practice she uses to get out of her head and get clear on what she knows, where she has gaps, and what support she needs. It’s a conversation about staying curious, getting uncomfortable, and continuing to learn as you grow. Pull up a chair, grab a drink, and join us Court-side. 💛 Want more conversations like this? Join Center Court Connections for monthly ideas, stories, and questions to help you hear yourself more clearly and take your next step with confidence: Center Court Connections | Center Court Collective Connect with Courtney 💛 LinkedIn: www.linkedin.com/in/courtneycheadley 💛 Learn more about Center Court Collective 🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial #CareerConfidence #SelfDoubt #WomenAtWork #CareerGrowth #WomenInBusiness #ImposterSyndrome #Networking #ProfessionalDevelopment #CourtsideConversations  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.

    Be a Sponge: The Career Advice That Helped Fran Carasco Grow

  4. Sep 18

    Taking the Opportunity Before You Feel Ready | Marci Oates

    What if you took the opportunity before you felt completely ready? Marci Oates started her career working in the cafeteria at HP and retired 30 years later as a Vice President of HR. Her career wasn't built by having every next step mapped out. It was built by saying yes to opportunities, taking lateral moves, asking for what she wanted, and continuing to move forward even when self-doubt showed up. In this episode of Court-side Conversations, Marci shares what her career looked like behind the résumé, including leading through one of the hardest moments of her career, finding the courage to speak up when she didn't feel supported, the advice that shaped how she approached her career, and the one opportunity she wishes she'd taken. If you've ever looked at an opportunity and wondered, "Am I really ready for this?" this conversation is for you. 💛 Pull up a chair, grab a drink, and join us Court-side. 💛 Want more conversations like this? Join Center Court Connections for monthly ideas, stories, and questions to help you hear yourself more clearly and take your next step with confidence: Center Court Connections | Center Court Collective Connect with Courtney 💛 LinkedIn: www.linkedin.com/in/courtneycheadley 💛 Learn more about Center Court Collective 🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial  #CareerConfidence #SelfDoubt #WomenAtWork #CareerGrowth #Leadership  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.

    Taking the Opportunity Before You Feel Ready | Marci Oates

  5. Aug 29

    When You Know It’s Time for a Career Change, But You’re Scared to Go | Rachael Greenwood

    What happens when you know it’s time for a career change, but self-doubt keeps you from making it? In this episode of Court-Side Conversations, I sit down with Rachael Greenwood, a teacher who spent more than a decade in the same school district and admits she stayed about three years longer than she knew she wanted to. We talk about the loyalty and self-doubt that can keep us stuck, what it really means to feel supported at work, and what finally gave Rachael the confidence to make a change. Rachael also shares the career advice that helped her realize she’s more than her job, why putting herself first felt so difficult, and the one thing she wishes she had done sooner. If you’ve been thinking about making a change but aren’t quite sure you’re ready, this conversation is for you. Pull up a chair, grab a drink, and join us Court-side. 💛 Want more conversations like this? Join Center Court Connections for monthly ideas, stories, and questions to help you hear yourself more clearly and take your next step with confidence: Center Court Connections | Center Court Collective Connect with Courtney 💛 LinkedIn: www.linkedin.com/in/courtneycheadley 💛 Learn more about Center Court Collective 🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial  #CareerChange #SelfDoubt #WomenAtWork #CareerConfidence #TrustYourself #CourtSideConversations  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 You Know It’s Time for a Career Change, But You’re Scared to Go | Rachael Greenwood

  6. Aug 15

    What I Wish I Would Have Known Earlier in My Career | Tamika Brunetti

    What would you do differently if you could start your career all over again? In this episode of Court-side Conversations, I sit down with Tamika Brunetti to talk about the lessons that took years of experience to learn. We talk about difficult feedback, knowing when you belong (and when you don't), self-doubt, self-awareness, the worst career advice Tamika ever received, and why she wishes she had started building something outside of her job much earlier. One of my biggest takeaways from our conversation? Know yourself. Don't tolerate the BS. And create value outside of your job. Because maybe some of the wisdom that comes with years lived is wisdom we can start embracing a little earlier. Pull up a chair, grab a drink, and join us Court-side. 💛 Feeling stuck or overthinking what comes next? Download my free guide, 4 Steps to Getting Unstuck, to help you get clearer and identify your next honest step: 4 steps to identify your next move | Center Court Collective 💛 Want more conversations like this? Join Center Court Connections for monthly ideas, stories, and questions to help you hear yourself more clearly and take your next step with confidence: Center Court Connections | Center Court Collective Connect with Courtney 💛 LinkedIn: www.linkedin.com/in/courtneycheadley 💛 Learn more about Center Court Collective 🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial #CareerAdvice #WomenInLeadership #CareerGrowth #SelfTrust #CourtSideConversations  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.

    What I Wish I Would Have Known Earlier in My Career | Tamika Brunetti

  7. Aug 3

    How to Know If You're Making the Right Career Decision | Randi Carlini

    Have you ever wondered if you're making the right career decision? In this episode of Court-side Conversations, I sit down with my cousin, Randi Carlini, to talk about what it looks like to trust your talents when life doesn't go according to plan. From earning a biology degree to building a career in hospitality, to stepping away from her career to raise her children, Randi shares the self-doubt, courage, and quiet confidence behind each chapter of her journey. In this episode, we discuss:  How to know if you're making the right career decision  Why your talents may matter more than your degree  The hidden self-doubt behind life's biggest decisions  The courage to choose a path that others may not understand  Finding purpose in every season of lifeIf you're questioning your next career move, wondering if you're on the right path, or struggling to trust yourself in a season of change, 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.

    How to Know If You're Making the Right Career Decision | Randi Carlini

  8. 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
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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.

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