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MARCH 2026

Dear Friend,

As International Women’s Day approaches, I find myself reflecting on the women who shaped me.

I think of my mother, whose strength was unwavering and who taught me there was nothing women couldn’t do. I think of a dear friend we recently lost, who believed fiercely in Pollyanna's work and whose conviction continues to guide me. And I think of the young women watching us now, learning what leadership looks like from the examples we set.

This year, that reflection feels heavier. In a moment when the rights and credibility of women continue to be challenged, and when stories of power shielding harm still surface with painful regularity, honoring women must mean more than appreciation. It must mean accountability. It must mean courage.

At Pollyanna, honoring women is inseparable from honoring all those whose voices have been marginalized or silenced. It means building communities where accountability is real, where leadership reflects lived experience, and where every person’s humanity is nonnegotiable. It means teaching young people to recognize injustice in all its forms and to respond with courage. It means refusing to normalize cruelty or the quiet erosion of rights.

To honor women now is to stand clearly for equity and respect for all who have been pushed to the margins. Not someday. Now.

Thank you for being part of a community committed to Building Stronger and Kinder Communities, especially when it matters most.

Warmly,

Casper Caldarola
Founder
 

LOOKING AHEAD

 
 

Pollyanna's Circle Membership 2026-27

Year-Long Learning. Stronger Communities. One Annual Fee. 

Join the Pollyanna Circle and equip your entire school community with the programs, tools, and inspiration needed to Build Stronger and Kinder Communities all year long. 

Become a founding member and gain expanded access to the resources schools rely on most from Pollyanna. Click here for more information and to register. And if you were a National Conference school, don't forget to add your discount code.

 
 
 

Early Pricing Ends 3/5 for Leadership Team Convening 

We’re excited to invite you to Resilient Leadership in a Time of Change, Crisis, and Conflict, launching in this April – created by Pollyanna and hosted by The Hewitt School and St. Luke’s School for NY tri-state schools.

Designed for senior leadership teams, this two-part convening strengthens alignment between mission, priorities, and decisions. Guided by Jason Craige Harris, we’ll engage in role-based discussions and intentional team planning, leaving with tangible takeaways, actionable insights, and a clear roadmap for mission-aligned progress. Click here to learn more and register. 

 

Teen Council March Meetup: Literacy and Allyship

Join us on March 8 for an interactive conversation with poet and educator Noah Arhm Choi, alongside PTC student facilitators. Together, we’ll explore how misinformation about trans and queer people spreads online, why it works, and how young people can interrupt harmful narratives in their own communities. Bring your questions and real-life experiences as we build practical tools for critical thinking, courageous allyship, and creating spaces rooted in dignity, safety, and belonging.

If you're 13-18 years old and would like to join a great group of students from across the country, fill in this form and we'll be in touch.

 
 

Derek & Gardy Headline Our March Online Workshops

Our workshops for the second half of the school year are filled with incredibly strong content and very much needed now. Please join us.

On Tuesday, March 3, Derek Lipscomb will examine what it really mean to have a seat at the table. Learn how to navigate those spaces with confidence and advocacy, and how your voice can open doors for others.

On Thursday March 12, Gardy Guiteau will explore how to build genuine partnerships with parents in fostering inclusion and belonging. Participants will reimagine how schools and families can co-create environments where every student thrives.

 
 
 
 

LOOKING BACK

Sleepless in Seattle

Casper Caldarola and Jason Cragie Harris flew to Seattle for Jason’s featured speaker session on Leading with Dignity at NAIS Thrive. It was an insightful presentation with great follow up questions. Thank you to everyone who stayed after Jason’s session, stopped us in the hallway, or reached out. So special to reconnect with longtime friends and meet new colleagues equally committed to doing this work well. We look forward to all the follow up.

 
 
 
 

New City School Night for Families

Pollyanna speaker Jason Craige Harris recently joined parents and caregivers at New City School in St. Louis to explore relational parenting and the power of cultivating a home culture grounded in dignity and empowerment. In a world that often rewards speed over presence and control over curiosity, Jason invited families to imagine homes where dignity is honored, dialogue replaces domination, and stability replaces reactivity. Relational parenting is not about perfection. It is about modeling the world as it should be so our children can experience it and carry it forward.

 

Miami Country Day Visit

Ahead of David Smith’s February Pollyanna workshop, Centering DEI in Advancement, Pollyanna Founder Casper Caldarola had the opportunity to visit Chief Advancement Officer David Smith, Senior Director of Academics Jason Asbury, and the GLOBE team. There is nothing more energizing than seeing this work in action — leaders who understand that advancement is not separate from culture, belonging, and mission, but deeply connected to it. At Miami Country Day School, fundraising, storytelling, and community engagement are aligned with the school’s values and academic vision. 

 
 

Buckingham Brown & Nichols in Cambridge

Jason Craige Harris delivered the keynote at BB&N’s Annual Community Day — a student-led day of learning beyond the classroom. Exploring a timely question — why are hard conversations worth having, and how do we do them well? — Jason challenged students to move beyond appeasing, avoiding, or attacking, and instead engage across difference with courage and dignity. By day’s end, they had begun building a practical toolkit for navigating conflict in school and beyond. Grateful to the student organizers and faculty at BB&N for creating space for courageous learning.

 
 

RESOURCES

A Strengths-Based Approach to Leadership and Teamwork

This is a full-day NYSAIS workshop on March 10 at The Allen-Stevenson School in New York City, led by veteran independent school leader and executive coach Katie Rocker . Designed to help educators build more inclusive and effective communities, the workshop uses Gallup’s CliftonStrengths framework to deepen understanding of how individuals naturally think, lead, and collaborate. Participants will explore their own talents, learn to value the diverse strengths of colleagues, and discover how differences can become assets rather than points of friction. Open to educators at all roles and levels, schools are encouraged to send pairs of colleagues. The fee includes the CliftonStrengths assessment, taken by more than 36 million people worldwide. Registration closes March 5.

 

Curriculum for Discussing Trauma and Resilience

Elizabeth Rosner’s acclaimed book, SURVIVOR CAFÉ: The Legacy of Trauma and the Labyrinth of Memory, is a rich, accessible, and informative work “mixing the personal with the historical, and the literary with the scholarly.” (~Viet Thanh Nguyen, Pulitzer Prize winner) 

The book provides an important resource for students in courses discussing: 

  1. epigenetics and the intergenerational transmission of trauma 
  2. the intersection between legacy and responsibility
  3. modern attempts to memorialize and commemorate victims of mass atrocities
  4. the biological, psychological, and emotional effects of the Holocaust; Slavery; the Cambodian Killing Fields; Japanese-American internment; the Rwandan genocide; 9/11; the bombing of Hiroshima and Nagasaki.

For more information, please contact: elizabeth@elizabethrosner.com.

 
 
 

ENDORSEMENT

“By creating spaces where everyone feels valued and heard, Pollyanna is not only building stronger communities, they are also laying the foundation for a more compassionate and harmonious world.” 

Laura Light, AAIE Executive Director

 

A FINAL THOUGHT 

"We realize the importance of our voices only when they are silenced." 

Malala Yousafzai

 
 
 
 
 
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