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JUNE 2025

Dear Friend,
 

As another school year winds down, I find myself thinking about what’s missing in so many of our spaces, and what’s possible when we decide to lead differently. At Pollyanna, we believe that Building Stronger and Kinder Communities isn’t a feel-good tagline. It’s a necessary response to the growing polarization, isolation, and injustice we see around us.

Over the past 10 years, we’ve walked beside schools and communities ready to engage deeply with curiosity, accountability, and hope. I’ve seen the power of this work up close: in a classroom where a student finally felt seen after sharing their story; on the Edmund Pettus Bridge, where our group stood in silence, absorbing both pain and possibility; in a school leader’s quiet moment of clarity about what inclusion really requires.

These experiences remind me that in the absence of kindness, fear grows. In the absence of strength, injustice persists. We need both to meet this moment—and to shape what comes next.

That’s why we're launching our inaugural National Conference in January 2026 in Minneapolis. We’re creating a space for people who are ready to listen deeply, share boldly, and build the communities we all deserve. Because stronger and kinder communities don’t happen on their own. They happen when we create them together.

Warmly,
Casper Caldarola
Founder
 

LOOKING AHEAD

 

Why is Charles Vogl Coming to Minneapolis?

Watch the video and join these amazing speakers in January 2026!

Jason Craige Harris – Conference Guide
Megan Hogan – Global Head of Talent, Goldman Sachs
Natosha Reid Rice – VP, Global Housing Opportunities and Mission Engagement, Habitat for Humanity International
Charles Vogl – Author, The Art of Community
Jamil Zaki – Psychology Professor and Author, Hope for Cynics 

Watch Charles or find out how to access the early pricing by 6/30/25!

 

Wherever Summer Takes You...

🏞️ the park
🏖️ the pool
🛋️ the couch
💼 the office
Join us on Zoom for our 2025 Summer Workshop Series, launching July 16! This dynamic PD series is designed for educators, administrators, and leaders committed to Building Stronger and Kinder Communities. Whether you're tuning in between meetings or beside a beach chair, our workshops fit into your summer rhythm.

Teen Leaders Needed for Next Year's Teen Council

Bring your voice! Teen’s opinions matter, and we're thrilled to provide a platform where they can share thoughts, ideas, and passions. Join us for informative and exciting monthly meetups on Zoom, specifically designed for 13-18 year old’s eager to engage in meaningful discussions on today's topics. Don't miss out on this incredible opportunity to make your voice heard and be a leader. Sign up and let us know you're interested.

 
 
 
 
 

LOOKING BACK

Our National Conference is in 6 Months

Casper Caldarola and Jason Craige Harris recently spent time at the Minneapolis Convention Center for a site visit. As real as the inaugural National Conference has felt since January, being there in person and seeing all the spaces where we’ll meet, connect and act to Build Stronger and Kinder Communities - made it even more real. The countdown is on -- the Pollyanna National Conference is just seven months away.

Early pricing ends June 30.

 
 

“Every Word Counts” The Power of Language

Some takeaways Jason Craige Harris shared with Middle Schoolers:
- Your words matter. They can build people up or break them down.
- Words linger. The brain stores not just the message but the feeling. 
- Be a builder. Say things like “I’m glad you’re here.”
- Speak up. Being an upstander doesn’t always mean confronting. It can mean checking in, asking a question, or calling someone in gently.
- Apologies and repair matter. It’s not about being perfect, it’s about being accountable, caring, and human.
- You are enough. And so is everyone else. Speak with dignity.

 
 
 
 

Final Teen Council Meetup of 2024-25

At the May 18 Pollyanna Teen Council meetup, How Powerful is the Teen Voice? Dré Finley, Inaugural Dialogue Facilitator at Williams College, invited us into a powerful conversation about grace, authenticity, and self-expression. He shared his journey as a Black trans man and reminded us that thriving is possible—even in the face of adversity—when we lean into what brings us joy and surround ourselves with care. Dré encouraged us to name our passions, affirm one another, and speak from the heart. And by holding space for teen voices, he reminded us how much power they already hold.

 
 
 

RESOURCE

We all need extra help at times...

Pollyanna’s Outside Resources page offers a curated collection of tools and materials to support individuals and institutions committed to Building Stronger and Kinder Communities. Organized by topic, this resource hub is dynamic and provides guidance and insight across key areas including:

  • LGBTQ+

  • Mental Health

  • Race

  • Religion

Whether you’re an educator, student, parent, or community leader, these resources are designed to deepen understanding and inspire continued learning on your journey toward inclusion and equity. Please share any resources you've found to be helpful. info@pollyanna-us.org

 
 
 

ENDORSEMENT

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

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