Ep. 27 - Pleasure Is Political: Cyclical Leadership & Raising Daughters Differently with Sheila Shupe

Rachel Wilson welcomes Sheila Shupe, Pleasure Coach, retreat leader, and master connector, for a bold and expansive conversation on feminine leadership, erotic embodiment, cyclical power, and building new structures for women. After 20 years in education, Sheila followed an unexpected calling into pleasure work and has since devoted herself to creating transformational women’s events and retreats that connect women through the power of the erotic.Drawing from her mentorship with Regena Tomashauer (Mama Gena) and her own lived experience of reinvention, Sheila shares why pleasure is not indulgent but essential — and why embodiment and erotic life force are necessary for women to expand into their full power. Together, Rachel and Sheila explore cyclical leadership in a linear world, motherhood and raising daughters with body awareness, the tension between structure and flow, and what it means to become a pussy-led businesswoman in an emerging and often unsupported industry.Sheila speaks candidly about her vision to build institutional-level support for women in coaching and erotic work — spaces where women can be held financially, structurally, and communally as they expand. At the heart of her work is a deep gift for seeing women’s light and creating environments where vulnerability, weirdness, and authenticity are fully embraced.Playful, visionary, and deeply affirming, this conversation invites listeners to listen to their bodies, trust their inner knowing, and imagine a future where pleasure, community, and feminine power are not fringe — but foundational.Learn more about Sheila’s work:sheilaeshupe.cominstagram.com/sheilaeshupe