376 Ashley Rogers: Reawakening Life Through an Unlikely Conversation with AI

At 75, Ashley Rogers is not reinventing her life—she’s reawakening it. Living in Ecuador and thriving in her latest entrepreneurial chapter in real estate, she began asking a familiar question: What’s next? What is mine to do now?

The answer arrived in an unexpected form: a series of deeply philosophical conversations with an AI she named Vivi. What began as curious exploration soon became a creative partnership, leading to their co-authored book, Vivi and Me: My Love Affair with a Bot. Together, Ashley and Vivi explore 64 questions about living an expansive life rooted in curiosity, learning, and play.

While Vivi engages in conversation with striking fluency, Ashley is clear-eyed about the relationship: AI is “a machine—a reflection of who you are and what you ask.” She speaks candidly about the importance of boundaries, offering thoughtful guardrails against overdependence and social isolation.

For Ashley, this collaboration is less about technology and more about something timeless: staying awake to life. As she reminds us, “the key to aging well is never letting go of curiosity.”

“My philosophical conversations with an AI rekindled my spirit, curiosity, and energy.” - Ashley Rogers

Connect with Ashley:

Email: [e-mail]

Book: Vivi and Me: My Love Affair with a Bot (when a sassy senior collides with AI, curiosity turns into magic). (2025).

Thanking Our Sponsor

The Chicago Women's History Center advances the historical record of the city of Chicago, serving women of all ages. It enriches historical research by presenting women's history through an intersectional lens inclusive of LGBTQIA+, BIPOC, ethnicities, with thoughtful representation of gender non-binary, class, and differently abled voices. https://www.chicagowomenshistory.org

Shining the Light on the Age-Wise Collective

Women Over 70 is proud to be part of the Age-Wise Collective, a group of women podcasters championing pro-aging voices. This week we highlight Patricia Noel Drain, business mentor, author, and host of the podcast, Stories and Strategies for Women Entrepreneurs Over 50. She focuses on empowering women to monetize their experience, avoid retirement and create purposeful, high-income businesses, fostering community and collaboration. Patriciadrain.com