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JULY 2025

Dear Friend,
 

Summer can seem like a season of slowing down and it’s also a season of growth. Beneath the surface, there’s reflection, recalibration, and quiet momentum. At Pollyanna, we’re using this time to deepen our partnerships, strengthen our team, and prepare for the important months ahead.

That includes the launch of our Summer Workshop Series on July 16, continued expansion of our Teen Council, and design of our inaugural National Conference for January 2026 -- a gathering rooted in connection, courage, and collaboration. Each of these initiatives reflects our belief that Building Stronger and Kinder Communities takes year-round commitment and care.

Because some of the most meaningful growth happens when we slow down, look ahead and tend to what matters most.

Warmly,
Casper Caldarola
Founder
 

LOOKING AHEAD

 

Why is Natosha Reid Rice Coming to Minneapolis?

Watch Natosha's video to find out! She will be our closing keynote at this groundbreaking three-day gathering. We will bring together educators and school leaders from across the country who are ready to listen deeply, lead boldly, and act. Through dynamic keynotes, interactive workshops, and meaningful connection, we’ll explore what it really takes to build communities grounded in equity, empathy, and purpose. If you believe a better future is possible and that it starts with how we show up in our schools, workplaces, and neighborhoods this conference is for you. More info and registration. 

If you would like to take advantage of the early pricing and need to wait until your new fiscal year, email us at info@pollyanna-us.org

 

3 Reasons to join our Summer Workshop Series

✅ Value
✅ Deep Expertise
✅ Convenience

Bring your entire school community together for a transformative learning experience! Our Series launches July 16 and features 12 workshops designed to deepen alignment with your mission and values—and it’s all available for one price per school.

Join 12 incredible facilitators presenting 12 important topics. See you on Zoom for our 2025 Summer Workshop Series.

 
 
 
 
 

LOOKING BACK

Welcome to Our New Trustees

We’re thrilled to welcome two extraordinary leaders to Pollyanna’s Board of Trustees: Celeste Herrera and Robin Walker-Randolph. Celeste, Head of School at The Calhoun School, brings a deep commitment to progressive education, social justice, and equity. With decades of experience at leading institutions, including Dalton and Penn, she brings both vision and heart to our mission. Robin brings many years of financial and operational leadership in independent schools and currently serves as CFO at Brooklyn Heights Montessori School. A strategic advisor and advocate for DEI in finance, Robin’s insight and steady leadership are invaluable additions to our board.

 
 

Our New Chief of Staff

We’re excited to welcome Dayna Campbell to Pollyanna. Dayna first became involved with us as a volunteer and Teen Council advisor, drawn to our commitment to student voice and school-wide transformation. “What kept me coming back was the care, the clarity, and the belief that real change is possible when we work together.” She brings over 10 years of experience as a project manager, facilitator and student affairs professional in higher education, with a deep passion for holistic student leadership, equity, and building community through dialogue across differences. Dayna now steps into this new role ready to deepen relationships, support our vision, and help steward the impact that makes Pollyanna’s work so powerful.

 
 
 
 
 

RESOURCE

Another Way Is Possible: An Invitation to Compassionate Dialogue

As many school communities continue to navigate heartbreak, division, and complexity, we find ourselves asking: How do we stay in community when the questions feel too big—and the pain too personal? In Another Way Is Possible—Circle, Compassion, and the Struggle to Belong Together, Jason Craige Harris offers a response rooted in dignity, story, and courageous compassion.

Drawing from his experience facilitating dialogue within a school board wrestling with belonging, antisemitism, anti-Palestinian racism, and the future of DEIB, Jason invites us into another way of being together. One shaped not by urgency or ideology alone, but by deep listening, shared humanity, and the sacred structure of the Peacemaking Circle.

At Pollyanna, we believe that Building Stronger and Kinder Communities begins with this kind of brave and tender work. We’re honored to share Jason’s essay as a resource, a mirror, and a guide. If you would like to bring Jason to your school, please email info@pollyanna-us.org

 
 
 

ENDORSEMENT

“As a member of the Teen Council, you’re empowered to lead, to take charge and to think about ways in which you can make change, but a lot of it is also about listening—to speakers, to your peers. In that way, you’re always learning.”
 
Former Pollyanna Teen Council Leader
 

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