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.