Court-side Conversations with Courtney

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.

Court-side Conversations with Courtney is a business podcast hosted by Courtney Headley, with 16 episodes on record and a Required Pod Score of 80.

Courtney Headley hosts Court-side Conversations with Courtney, a business show with 16 episodes published.

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  Episode #15

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

  Sep 25, 202618 minS1

  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.

  ListenShow Notes
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  Episode #14

  Taking the Opportunity Before You Feel Ready | Marci Oates

  Sep 17, 202621 minS1

  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.

  ListenShow Notes
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  Episode #13

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

  Aug 28, 202614 minS1

  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.

  ListenShow Notes
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  Episode #12

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

  Aug 14, 202620 minS1

  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.

  ListenShow Notes
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  Episode #11

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

  Aug 3, 202616 minS1

  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 life If 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.

  ListenShow Notes

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