Pitcairn’s Women of Wealth Retreat

The Power of Story: Crafting Narrative, Connection, and Legacy

Naples, FL — March 3–4, 2025

Over the course of two transformative days in Naples, FL, Pitcairn invited women wealth owners to gather for a holistic retreat centered on a timeless and powerful theme: the stories we tell—about ourselves, our families, and our legacies.

Amy Hart Clyne, our Chief Knowledge & Learning Officer, opened the program by inviting attendees to reflect on their journeys. In her session, Building Community Through Story, Amy emphasized the importance of personal narrative as a vehicle for connection, empowerment, and generational wisdom. Her message: our stories shape how we show up—for ourselves and for others. In sharing a sample of the stories featured in her book, Amy shared a favorite quote: “Everybody has a story. Everybody’s story matters. Nobody gets the story they want.” We gave our participants a chance to discuss their stories, to reclaim and rewrite them in a safe space. Like those in Amy’s book, we were reminded that our mess can be message.

Following this opening, Keith Mercurio, president of Ethical Influence, guided participants through Women as Leaders: The Art & Science of Inspiring Change. His session introduced a four-part framework designed to help attendees understand their influence—not only through words and actions, but through the stories they tell about their values, leadership, and family roles. He helped us develop our own personal mantras and challenged us to move away from “should/shouldn’t” thinking to a “could” mindset that leads to more possibilities.

The retreat’s storytelling theme came to life in a powerful way during Owning Your Story, a lively session led by Amy Glass, CEO of BRODY Professional Development. Participants explored their personal “hero’s journey,” identifying key turning points, values, and life lessons that have shaped who they are today. Glass provided a practical structure to help our attendees tell their stories with clarity and confidence—making space for both vulnerability and strength. The session also gave us a creative outlet with a chance to do some fun improvisational exercises together.

After lunch, the storytelling lens shifted toward the rising generation. In Raising Resilient Families, Diana Clark, president of Intent Clinical, encouraged our attendees to recognize how the stories we tell as parents impact our children’s resilience. She challenged participants to be intentional in shaping family narratives that both nurture empathy and foster independence. After the session, several of our guests approached Diana wanting to know more. Dealing with the everyday challenges our children face and teaching them resilience was a topic that deeply resonated with our group.

Later, Cathy Carroll, president of Legacy Onward, tackled the deeply human challenge of family conflict in A Brave Approach to Solving Hidden Conflict. Drawing from her book Hug of War, Carroll introduced “Both/And Thinking” as a tool for rewriting the internal and external stories we tell when tensions arise—transforming blame into understanding and conflict into opportunity. Cathy did a tremendous job sharing her own journey but also exposing how we can really challenge ourselves to create win-win situations in any conflict. Several attendees shared some of the family challenges they were currently facing, and creative solutions flowed through collaboration and discussion.

Day Two opened with Table Talk Peer Discussions, a signature Pitcairn experience that brought storytelling full circle. Conversations facilitated by Pitcairn’s Relationship Managers encouraged our attendees to exchange insights and personal experiences—proving again that some of the most powerful stories are those shared among peers.

Next was Calling “Time Out” with Eliza Orleans, principal at CFAR, where we examined the unconscious narratives we carry within ourselves about productivity and busyness. Her neuroscience-informed session offered a new story: that creating space in our lives is not a luxury, but a necessity for clarity, purpose, and creativity.

The retreat concluded with a dynamic session by Alison Fragale, author of Likeable Badass. Her talk explored how status and influence are shaped by the way we tell our stories—both to ourselves and to the world. Alison empowered our attendees with strategies to claim their space and communicate their value with authenticity and impact.

Throughout the retreat, one idea echoed across every session: our stories matter. They reflect our leadership, our values, and our legacy. Looking ahead, we hope to make this event an annual retreat. We plan to keep the momentum going for this year’s group of attendees by scheduling a virtual gathering in the coming weeks. Stay tuned for future details.

Whether spoken around a table, shared in a workshop, or passed from one generation to the next, storytelling remains one of the most powerful tools we have to connect, inspire, and lead. We look forward to continuing to build spaces where women wealth owners can come together and grow.