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 13 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Courtney Headley hosts Court-side Conversations with Courtney, a business show with 13 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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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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  Episode #10

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

  Jul 17, 202619 minS1

  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.

  ListenShow Notes
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  Episode #9

  When Everyone Starts Looking to You for Answers | Kate Coelho

  Jul 3, 202620 minS1

  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.

  ListenShow Notes
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  Court-side Conversations with Courtney

  Know Your Strengths, Trust Yourself More | Jocelyn Guite

  Jun 19, 202618 min

  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.

  ListenShow Notes

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