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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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What if you let go of the rulebook and gave yourself permission to create a life that feels like a dream you actually want to be living? This week on the School of Midlife podcast, we’re talking to Wendy Harrop—a retreat host, event planner, and farm-dwelling dream-weaver—who did just that.
After years of living the good-girl life, checking the boxes, and doing what was expected of her, Wendy woke up to a deeper longing: one where she gets to be the main character. She didn’t burn it all down in a blaze of midlife crisis. Instead, she took one brave step after another—choosing joy, curiosity, and adventure over obligation.
In this powerful conversation, Wendy shares the story of how she moved from California to a 200-year-old farm in Massachusetts, why hosting retreats for women is her calling, and what it means to live with delight, even when things don’t go according to plan. Whether you’re feeling stuck, restless, or just quietly wondering “is this all there is?”—this episode will remind you that midlife isn’t a dead-end... it’s a damn invitation.
👂 In this episode, we talk about:
- Letting go of shoulds and embracing your actual desires
- What it looks like to be the curator of your own life
- The power of women gathering in intentional, beautiful spaces
- Living with delight—even when life throws curveballs
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