Fearlessly Facing Fifty And Beyond

EP209: Breaking Free from the Need to Please: A Conversation with Amy Wilson


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The silences that follow our "no" speak volumes. As women, we've mastered saying the word itself, but it's what happens after—that uncomfortable pause—where we often surrender our power.

In this eye-opening conversation, author Amy Wilson discusses her new book "Happy to Help: Adventures of a People Pleaser," revealing how deeply ingrained the people-pleasing tendency becomes in women's lives. When Amy tells us that people-pleasing is "putting other people's wants and needs before your own," she's describing the unspoken assignment given to every mother, every woman. Yet this societal expectation exacts a serious toll, from strained relationships to physical illness.

What makes this discussion particularly powerful is Wilson's ability to distinguish between life's unavoidable challenges and the optional burdens we assume. "When you've got a sick parent and a sick kid at the same time, you're not a people pleaser—you're just somebody with too much on your plate," she notes, helping listeners separate necessary responsibilities from those taken on purely out of obligation or need for external validation.

The conversation explores "socially prescribed perfectionism"—the researched phenomenon where women internalize impossibly high societal standards—and offers refreshing perspectives on female friendships, writing discipline, and self-compassion. Wilson's advice to her younger self resonates deeply: "When hard times come, they're hard because they're hard, not because there's anything wrong with you."

Whether you identify as a people pleaser or simply find yourself perpetually overwhelmed, this episode provides both validation and practical wisdom for reclaiming your boundaries without sacrificing meaningful connections. Listen now for a transformative conversation that might just change how you respond the next time someone asks for "just one more thing."


Connect with Amy Wilson Click here:


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Fearlessly Facing Fifty and Beyond has over 200 episodes with inspiration and stories to age fearlessly and connect confidently to others thriving at midlife and beyond.

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Fearlessly Facing Fifty And BeyondBy Amy Schmidt

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