June 2021 Update from Pollyanna
A Note from Pollyanna Founder Casper Caldarola
As media outlets across the country have explored the social justice reckoning on independent school campuses, some of you may have seen Pollyanna in the news. With only a small number of exceptions, we’ve chosen not to engage in these stories and our lack of participation may be contributing to a number of inaccuracies.  
There is one consistent inaccuracy I’d like to address: that our work and curriculum are about amplifying the past in such a way as to make white students and adults feel shame. Those of you who have worked with us know this couldn’t be further from the truth. We’ll continue to counter this sentiment in everything we do. Our work is about uplifting and building compassion and empathy in children at a vitally important developmental period.
June 2021


In our September 2020 newsletter, we framed the upcoming school year by quoting Ashley McCall, a 3rd-grade teacher in Chicago Public Schools, in an article she wrote for the blog Chicago Unheard:

“What if we listened? What if we made space to acknowledge the anger and demands of students? What if our priority was healing? Individual and collective. What if we respected and honored the work of healers and invested in healing justice?”

It feels appropriate to revisit these all-important “what if” questions in June of 2021, especially as backlash and resistance to the movement for equity and racial justice create obstacles to progress. As some voices work to preserve an unjust status quo through a denial of systemic racism, sensationalizing DEI work in sympathetic media outlets, or simply by trying to apply a “colorblind ideology” to a world that clearly sees and responds to color, the “what if” questions in McCall’s blog post remind us that the greatest desire for change, justice, and healing comes from those who will inherit leadership and stewardship of our society.

As we considered topics for this month’s newsletter, we recognized there was much to denounce, commemorate, memorialize, and celebrate right now.
  • The horrific rise in anti-Semitism and Asian hate crimes.
  • The first anniversary of George Floyd’s murder and the movement for racial justice it elevated, renewed and energized.
  • The 100th anniversary of the Black Wall Street Massacre in Tulsa and the fight to appropriately memorialize this tragic event.
  • Pride Month this June, when we hope more of us can gather together safely to celebrate and advocate for the LGBTQ community.

Any one of these incredibly worthy individual topics could fill the introduction of our monthly newsletter. Rather than choosing between them, we want to lift up all of them and name what they hold in common: networks of committed, resilient, caring individuals willing to navigate resistance to create more equitable and just communities. 

In his keynote speech at the Dalton Conference, 2020: What Did We Learn? How Will We Continue to Move Forward?, Dr. Rodney Glasgow perhaps put it best:

 “You meet resistance with resilience. You show up every time because it matters. It’s that important.”

As summer approaches, many of us might begin to think about how we will rest and restore ourselves in the coming months. We also hope you will think about how you personally can “meet resistance with resilience” as we continue our work through the summer and into the next school year.  

  • How can we continue to put our energies into forwarding action, progress, and positive change in the face of fear and resistance? 
  • As resistance to change mounts, how can we continue to bounce back to support and lift each other up? 
  • How might we continue to center children in our efforts to create a more equitable and just world?

With good wishes for a restful, restorative, and resilient summer,

Casper Caldarola

In the News

Ravenscroft Hosted Inaugural Conference
Ravenscroft's Creating Inclusive Communities Conference was entitled Race, Privilege and Belonging. It focused conversations on how race and privilege impact a sense of belonging at schools. Participants shared effective practices and called upon fellow communities to problem-solve and find meaningful solutions. 
The Homeroom Column 
Some keen insights in The Atlantic about the importance of racial literacy curriculum from two former independent school teachers who are currently co-founders of Teachers Who Tutor NYC.
Teen Pollyanna Member
Stay tuned for more thoughts from Pollyanna student interns spending this summer developing the Teen Pollyanna initiative. If you're a high schooler or know someone who would like to join us or learn more, please email info@pollyannainc.org
The 11th Annual Dalton Conference
The Dalton Conference gave time to consider the progress made, the roadblocks encountered, and the support needed to make tangible movement. The conference was attended by 26 NYC independent schools that made action plans to become more equitable institutions.


Pollyanna Position Paper V: Naming and Navigating Pushback to DEI Work
Many school leaders had to reckon with resistance against their diversity, equity, and inclusion efforts this year. The 5th Pollyanna Position Paper invited School Heads and DEI Directors to name strategies for navigating challenges while trying to lead their school communities towards greater racial justice and equity. Click here to read PPPV.
2021-22 Professional Development & Workshops
Mark your calendars for our 3-Hour Curriculum Overview Open PD on Saturday, August 13 and Saturday, October 23, from 1:00-4:00PM ET. In addition, we're excited to announce the addition of a special Workshop for Communications Directors. We will announce more of the schedule and include registration links for Pollyanna-hosted Professional Development & Workshops in our July newsletter. Till then, the second cohort schedule for Showing Up and Standing Up is below:
Showing Up and Standing Up: A 5-Part Journey Towards Antiracism for White Adults with Jay Golon and Jessy Molina
1 September 2021, 7PM ET, “I don’t really see race...” - Examining White Identity
6 October 2021, 7PM ET, “I’m the least racist person…” - Unpacking White Privilege and Powe
3 November 2021, 7PM ET, “I don’t want to say the wrong thing…” - Navigating Conversations about Race
1 December 2021, 7PM ET, “I feel like I don’t know how to help...” - What Does it Mean to be an Ally and Accomplice?
5 January 2022, 7PM ET, “I just want to do the right thing...“ - Committing to an Antiracist Life
Please click here to register for the second cohort of this 5-Part Series.
School Conferences 2021-22
Join Far Brook School, Dalton School, Francis Parker School, Harvard-Westlake School, Ravenscroft School, Town School for Boys, Tuxedo Park School, Vermont Academy, Watkinson School, and others as a host school of our Intra- or Multi-School Conference models next year! For more information, please email info@pollyannainc.org
New Schools Working with Us
Welcome to: Brockton School District, MA; Chilmark School, MA; Dedham Country Day School, MA; Friends Community School, MD; Hoboken Charter School, NJ; Paideia School, GA; Sudbury School District, MA; and Watkinson School, CT.
Pollyanna advances systemic change by developing stronger communities.
Pollyanna works with academic and other institutions to achieve their diversity, equity and inclusion goals. Through its unique conference models, discussion platforms, and racial literacy curricula, Pollyanna increases cultural competence.
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Pollyanna, Inc. is a NY not-for-profit corporation 501(c)(3).
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