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. 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

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. 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
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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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