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MARCH 2025

Dear Friend,
 
As we celebrate Women’s History Month, many of us have been inspired by the trailblazing women who came before us and stand in awe of the women currently doing impactful work. I hope we all have at least one woman in our lives who has left a lasting impression. For me, that woman is my mother.
 
Born in Brooklyn, my mom was the first in her family to graduate from college, one of the few women to rise as an advertising executive and eventually started her own agency. She wore pantsuits with pride, championed causes like Planned Parenthood, loved science fiction novels, Broadway, and playing the piano. She knew right from wrong, valued kindness, and fiercely loved her two children and four grandchildren.
 
As Pollyanna turns 10 this year, my mom has missed much of its journey, but her voice is ever-present in my life. Whether questioning a decision I’ve made or simply cheering me on, her words are a constant guide. More than anything, I hear her reminding me to stay true to my values, to prioritize kindness, and to find the strength to be fearless. At times, this feels daunting, but I remind myself that change can begin with small actions.
 
If you’re unsure where to start, begin small. Choose kindness in your daily interactions. Speak up when you see injustice. Whether through attending local events, supporting community initiatives, or advocating for policy change, every action helps create a more just and compassionate world.
 
I invite you to join Pollyanna as we continue to Build Stronger and Kinder Communities. Together, through meaningful dialogue, we can forge a future where everyone understands their inherent worth and lives with the unshakable certainty that their rights are protected.
 
With love and strength.
Casper Caldarola
Founder
 

LOOKING AHEAD

 

Early Pricing Ends March 15

Even though summer feels far away, get a taste of it now with the introduction our new series: Renewing Your Commitment to Your School’s Mission and Values. We are once again offering topical workshops with dynamic facilitators for one price for all 12 workshops for all of your school employees. In addition to participating live on Zoom, each workshop will be recorded, and archived and available to view until August 31. Click here to see this incredible line up and register your school before March 15 for the pre-sale price. 

Naledi Semela: Because We Are: Reframing Disagreement, Embracing Differences 3/11/25

This workshop will examine why and how strong teams make the most of those times when we see the world differently. In a polarized environment, it is essential we maintain that diversity is our strength and not an inconvenience. A problem solving exercise will illuminate the best practice of seeking different perspectives and navigating disagreement. 

 
 
 

LOOKING BACK

 

Dalton Conference

The 15th Annual Dalton Conference took place on February 8 – Dignity Through Dialogue. Keynote Jason Craige Harris welcomed the 27 NYC independent schools that joined us for this day of connection, learning and action. As always, the student panel was impactful as they shared their experiences and what they need from their schools. Thank you to all the School PODs for spending the day working on making your communities stronger.

 
 

Courage & Resources in the Face of Fear

Many teachers are caught now between students and parents. Or between conservative students and liberal students. Or between families on this side and families on that side. Ali Michael’s workshop was for educators who desire to build courage and resources in the face of fear. She shared personal stories and offered materials to support educators.

 
 
 

Canceling Cancel Culture

Understanding that schools are a microcosm of our society at large, participants in this session unpacked how the many iterations of cancel culture impacts teaching and learning in 2025. Shanie Israel and Paris McLean's workshop attendees walked away from this timely session with tools and strategies to navigate and curb cancel culture within their classrooms and school communities. 

 
 
 

What Boys & Girls are Made of

Rosetta Lee's 3 insightful workshop takeaways:
1 - Gender and sexuality inclusion serves ALL of our students.
2 - Gender and sexuality police each other in our society to limit the authentic expression of our students.
3 - ALL students, no matter how they identify or express, deserve to be seen, heard, treated fairly and protected.

 
 
 

Leading a Community

Mission as an Anchor – In times of cultural and political turmoil, a school’s mission and values provide stability. Leadership should consistently return to these core principles to guide decision-making.

Clarity & Transparency Build Trust – Clearly defined norms, guardrails for speech and behavior, and restorative conflict-resolution protocols help communities navigate challenges with integrity and accountability.

Dialogue is a Skill—Teach It – Schools must actively equip students, faculty, and families with the tools to engage in meaningful conversations across differences. Practicing real-world scenarios strengthens the community’s ability to navigate conflict constructively.

 
 
 

RESOURCES

Reframing Conflict

In an era of growing division, disagreement often feels like a zero-sum game, making consensus difficult. But what if conflict could be an opportunity to strengthen relationships? In the new book, Conflict Resilience: Negotiating Disagreement Without Giving Up or Giving In (HarperBusiness, March 18, 2025), former Harvard faculty Robert Bordone, a conflict management expert, and Joel Salinas, M.D., a leading behavioral neurologist, show how conflict can benefit everyone. They present Conflict Resilience—a skillset and mindset to embrace disagreement and grow from it—offering practical, neuroscience-based solutions and a three-step framework to navigate conflict effectively.
 

Call For Kindness

We are proud to partner with Rileys Way Foundation to share their Call For Kindness, which offers young change makers (ages 13-23) the chance to participate in a dynamic Leadership Development Fellowship and win up to $5,000 in funding for a project that inspires kindness and strengthens their local, national, or global communities. Applications close on March 9, 2025. For more info www.CallForKindness.org.

 
 
 
 

ENDORSEMENT

This session not only empowered me to effectively advocate for inclusive learning experiences, crucial for our students' holistic development, but it also validated my efforts as a leader in fostering a more equitable and supportive learning environment for all. I am deeply grateful for the opportunity to learn alongside you.
 
Ana Brunson, Village Community School
Attended: The Enduring Need for Inclusive Curriculum with Sam Hosein
 

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