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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode, we’re diving into one of the most fascinating mirrors of modern womanhood — Taylor Swift. Her latest album has stirred up endless opinions, especially from women’s empowerment coaches calling her “too much,” “too salesy,” or “narcissistic.” But here’s the truth: what we judge in others often reveals what we haven’t yet faced in ourselves. This conversation isn’t really about Taylor — it’s about how deeply our collective “good girl” conditioning still runs, even in spaces that claim to be liberated.
We’ll unpack what good girl conditioning actually is — that invisible script telling women to be successful, but not too successful. To be pretty, but not too pretty. To make money, but not too much. It’s the constant dance between being “too much” and “not enough,” and it quietly dictates how we show up in our businesses, our relationships, and our self-expression.
I’ll share how this programming sneaks into your marketing, your prices, your voice online — and how it keeps powerful women apologizing for their ambition. You’ll learn how to spot it, interrupt it, and ultimately give it a big f*ck you. We’ll talk about the real work of taking up space, raising your prices, and celebrating your visibility without waiting for approval.
Because here’s the truth: you can’t win, and you don’t have to. There will always be critics. There will always be noise. Like Taylor, your job isn’t to please everyone — it’s to stay in integrity with yourself.
If you’re ready to stop shrinking, stop over-explaining, and start building a business that reflects your full power, this episode will give you the permission slip you’ve been waiting for. The good girl doesn’t build empires — the bold woman does.
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