| | Dear Friend, At a time when cruelty is too often normalized and division grows louder than connection, Pollyanna is committed to helping schools choose a different path. Every week this fall, we have partnered with educators, trustees, students, and families who refuse to accept that polarization and fear are the only possible outcomes. In classrooms, boardrooms, faculty rooms, and virtual spaces across the country, we are witnessing something powerful — people choosing courage and compassion. Through our workshops, leadership coaching, school assessments, and student programs, we continue to support school communities in building cultures where dignity is practiced, not just promised. Our 2025–26 Workshop Series is now underway, and our Teen Council meetups have begun connecting students across the country who are eager to learn, lead, and shape change in their schools. And ahead on the horizon, our National Conference in January 2026 will bring together school community leaders who believe in the possibility of progress and the responsibility of action. Jason is already in Minneapolis waiting for us! As we move into the holidays, we are grateful for the schools and partners who continue to stand with us in this work. Now is the time to step forward. Join us, learn with us, and lead with us. Together we will continue Building Stronger and Kinder Communities. Warmly, |
|  |
|
| | November's Workshop Series Line Up It Takes Just One: How Educators Can Transform the Lives of LGBTQ+ Students -- Learn how educators can protect and affirm LGBTQ+ students amid anti-trans legislation. Gain inclusive practices, strengthen policies, and dispel myths through a holistic lens. Leave with tools to safeguard students and advance gender equity. Belonging Through Shared Humanity: Dignity, Adolescence, and the Stories We Tell -- Explore how dignity and storytelling shape school culture. Understand how adult narratives influence adolescent belonging and how youth thrive when adults model shared language and respect. Walk away with strategies to build connection across roles and generations. Sign up for the 2025-26 Series. Join us! |
|
|
| Equity in Advancement at the National Conference Watch why David Smith, Chief Advancement Officer at Miami Country Day School, is conducting this workshop: The Business Case for DEIB: Socioeconomic Diversity and the Future of Independent Schools. He will explore how budgets can reflect values—fueling access for students, supporting faculty, and strengthening community—while keeping schools mission-driven and financially strong.
The Pollyanna National Conference will spark ideas, challenge assumptions, and equip you with strategies to reimagine what’s possible in independent schools—register today! Join us in Minneapolis for this workshop and many, many others! |
| |
|
| Teen Council: The Science & Soul of Connection Educator and social-emotional learning specialist Megan Saxelby explores the role of authentic connection in personal well-being, leadership, and community resilience. Participants will learn strategies to strengthen relationships and foster supportive, thriving communities. Led by our incredible teen leaders and supported by Pollyanna’s dedicated adults, the Council is a space for discovery, leadership, and connection. Fill out this short form if you’re 13 to 18 years old and interested in attending this year. Watch the Council's video and join us on November 16. |
| |
|
| | We're Just Getting Started Thank you to everyone who joined us to celebrate Pollyanna’s 10th Anniversary Breakfast. The energy in the room reminded us why this work matters because when people come together with purpose, possibility grows. Celebrating our first Board Chair Ashley Smyth and Teen Council Co-creator Addeson Lehv, Jason Craige Harris and Casper enjoyed highlighting ten years. We’re just getting started. Be part of the next chapter of Building Stronger and Kinder Communities. Please enjoy our video and reading our Ten Stories for Ten Years. |
| | Pollyanna Young Leaders is Launched We’re thrilled to announce the launch of Pollyanna Young Leaders (PYL) a new community of 25–35-year-olds dedicated to Building Stronger and Kinder Communities. As part of our 10th Anniversary celebration, we’re inviting young professionals to join our founding New York cohort. Together, we’ll connect, learn, serve, and shape the future of a national nonprofit committed to equity and belonging. Ready to lead the next decade of kindness in action? Add your name to this form and we’ll be in touch. |
|
|
| | |
|
| Chicago was Inspiring Especially now Chicago, you inspire. Casper Caldarola met with schools that are deeply committed to supporting their communities. Energized by leaders who are not just talking about change, but building it every day with intention, courage, and care. Excited for what’s ahead together. Thank you to Latin School of Chicago and Near North Montessori School. Also loved spending time with Jason Craige Harris, Shernice Lazare and Anthony Witte – we’re never all in the same city! |
|
|
| | Harvard-Westlake Does it Again On October 25, Casper attended Harvard-Westlake's 9th Pollyanna Conference, Minds of All Kinds: Inclusive Learning, Limitless Possibilities. The gathering brought together 29 Los Angeles independent schools all committed to deepening inclusion in their communities. A central takeaway: independent schools are confronting the tension between academic rigor and authentic inclusion. Many are redefining achievement—moving beyond metrics toward growth, self-advocacy, resilience, and empathy. Normalizing difference means celebrating many ways to learn, lead, and succeed. |
|
|
| | Transformative Steadiness Pollyanna is partnering with Bank Street School for Children on a powerful, skills-based series focused on having hard conversations—and doing so with transformative steadiness. We’re exploring William Ury’s Getting to the Balcony model, integrating self-regulation, reflection, and strategy to navigate difficult dialogues with clarity and care. This series is intensely practical: participants work with real scenarios, try out grounded scripts, and build muscle memory for moments that matter. The goal: more courageous conversations, less reactivity, and stronger relationships across the community.
|
| |
|
| | | | 2026 BLAC Gathering Join the Black Affinity Collective (BLAC), February 13–15, 2026, at The Mount Vernon School in Atlanta, GA. Centered on the theme Ubuntu: I Am Because You Are, this Gathering brings together Black professionals in independent schools to celebrate community, empowerment, and joy. Through panels, workshops, and reflection, participants will connect with peers, share experiences, and explore strategies for thriving and leading change in their schools. Together, we’ll honor our shared stories, uplift one another, and build lasting connections across the Black diaspora in independent education. Learn more and register. Align & Advance: Communications-powered Strategic Planning from Stony Creek Strategy While schools often invest a great deal of time and other resources into establishing a strategic vision, they often struggle to bring that vision to life. We believe that your strategic planning process will be more inclusive, and more impactful, if it’s grounded in alignment, establishing a shared reality. We know that once a school community communicates honestly and comes into alignment, they develop vital clarity around their vision and commit to shared investment in the work required to achieve it. The process is led by two deeply experienced school professionals, one a former head and the other who has served as a chief communications officer, both understanding the momentum unleashed when strategy and communications come together. For more information, contact Julie Faulstich: jfaulstich@stonycreekstrategy.com |
| | | | “I think it’s a moment where Pollyanna’s model is needed more than ever. That combination of conversation and structure…it’s what allows people to not just feel things, but actually do something with what they feel.” Ashley Smyth, Pollyanna’s first Board Chair |
| | A FINAL THOUGHT “You cannot get through a single day without having an impact on the world around you. What you do makes a difference, and you have to decide what kind of difference you want to make.” Jane Goodall |
| |
|
| | | | Pollyanna, Inc. is a not-for-profit corporation 501(c)(3). © 2025 Pollyanna | New York, NY 10075 |
|
|
| |
|
|
