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Society & Culture

How to Win When People Underestimate You with Taylor Rooks

podcast October 21, 2025

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#315: If you’ve ever felt underestimated, this episode is for you.

Taylor Rooks is one of the most respected sports journalists in the game — and not because she plays it safe. She’s built her career on asking fearless questions, trusting her gut, and refusing to shrink herself to fit into anyone else’s idea of who she should be.

In this conversation, Taylor and I talk about what it means to be a woman who takes up space and why the pressure to be palatable isn’t worth giving in to.

We talk about ambition, integrity, reinvention, and the deep self-trust it takes to keep showing up when you have a big vision for your life. Taylor doesn’t just bring her voice to the table — she brings her values. And you can feel it in everything she does.

We talk about:

  • How the experiences of women in sports mirror broader societal beliefs
  • Why it’s powerful not to respond to every critic
  • The art of asking better questions (in life and interviews)
  • Knowing your value, even when others want you to shrink
  • Building a career that reflects your values, not just your resume
  • How to trust yourself when the opinions of others become too loud

Episode Links:

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Please note that this episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct or indirect financial interest in products or services referred to in this episode.

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