August 2021 Update from Pollyanna
August 2021
Dear Friend,
It was 13 months ago – July 7, my birthday, to be precise – that I got the call. I had had a nagging, persistent sore throat for some time. Since it was the middle of a pandemic, and I was already pretty anxious, I had no shortage of imaginary culprits. Despite my vivid imagination, tonsil cancer had not been on the list.
As a New Yorker, we were already floating in a surreal and uneasy time. By July, the morgue trucks had settled outside Lenox Hill Hospital and the hospital tent had been stationed in Central Park, outside Mount Sinai. Within my family circle, I was isolated, and with each passing day, more concerned about my son 3,000 miles away.
My diagnosis came at an unprecedented moment in my professional life, too. Until then Pollyanna’s projects were all in-person. But, in March, as our scheduled professional development and conferences were cancelled or postponed, I began to feel as though Pollyanna would join the list of organizations paused or ended by the Covid crisis. 
Shortly thereafter, the senseless murder of George Floyd prompted a reckoning around the nation, world, and within independent school communities, most loudly echoed on Black@ social media accounts. And in this reckoning, schools recognized that significant work around diversity, equity and inclusion could not pause until the end of this pandemic. They accepted that even when not physically together, equity could not be presumed, and important steps toward cultural recompense could and must be taken.
For Pollyanna, not only did this feel like a moment of transformation; it felt like a moment to make tangible strides towards fulfilling our mission of developing stronger communities. In May and June, the phone began to ring again and we quickly pivoted to a robust calendar of virtual programs for school communities and businesses seeking to engage their communities in dialogue around DEI topics. 
Then, July 7. After many doctor appointments, tests and scans, in August I began a difficult seven-week course of radiation and chemotherapy treatments. In a moment of great professional challenge, I was, on most days, too depleted to will myself out of bed.
And, yet another challenge...some opponents began pushing back against the racial-justice dialogue taking place in independent schools. And as I continued to recover, Pollyanna seemingly became a prominent target in these efforts.
In the media, my colleagues and I were battered with allegations and untruths: that we sought to indoctrinate students in a political philosophy; that I misrepresented my heritage as a white, Jewish woman; that I was an opportunist getting rich off racial justice. The online vitriol was harsh, and I felt at times unsafe in my own home and had to take appropriate measures.
In a period of unimaginable challenges, I drew enormous strength from my communities -- especially our amazing Pollyanna team, close friends and my son, who moved back to New York. It was tempting to withdraw -- from the work, the challenge, everything. But the convergence of Covid, cancer and conflict had one resounding takeaway for me: that we need to confront our fears and challenges, and that when we commit to the hard work, we discover strength and resilience we did not even know we had.
Today, my health has greatly improved, yet I do not feel entirely out of the woods on any of these fronts. At the same time, as I begin to put this convergence of challenges behind me, I feel stronger and even more steadfastly dedicated to Pollyanna’s mission.
This is the first time I am publicly sharing the personal and professional challenges I experienced during this past year. It feels important to reflect on this time and on the value of getting through adversity. We all become stronger when we confront what’s difficult. No doubt, we will continue all to face challenges in the year to come. I am deeply grateful for this community, for your partnership, for your support, and for your trust in our shared mission.
All best,
Casper Caldarola

In the News

K-8 Racial Literacy Curriculum Interactive Workshop
Join us for an interactive 3-hour overview and in-depth discussion of Pollyanna's K-8 Racial Literacy Curriculum with Jason Craige Harris. Saturday, August 14 from 1:00-4:00PM ET on Zoom. Please download our free K-8 Racial Literacy Curriculum and see Announcements below to register.
Pollyanna Conferences 
These are a few potential outcomes of hosting a Pollyanna Intra-Conference. Is your school ready to explore how it can offer a platform for meaningful dialogue and create a more inclusive community by taking concrete action? We would love to help. For more information about hosting, please email
New Workshop for Communications Professionals
Join Jan Abernathy, independent school communications leader, as she discusses what it takes to build meaningful and effective partnerships with school diversity, equity, inclusion, and belonging teams. Tuesday, August 10, 2021 from 2:00-3:00PM ET on Zoom. Please see Announcements below to register.
Pollyanna Babies
Join us in welcoming to the world three new Pollyanna babies: Waverly, Whit, and Saya. These three will no doubt be just as committed to creating inclusive communities as their mommies, who have all played a pivotal role in supporting our work over the years. We are so thrilled to see our Pollyanna family growing!


Pollyanna Position Paper VI
During the last year, we’ve shared our Position Papers that included the voices of Students, Heads of Schools, DEI Directors and Communications Directors. We’d love to hear from parents and guardians. If you’re a parent or guardian, please fill out this short, anonymous form. If you work at a school, please share with your Parents Association. Many thanks!
Upcoming Professional Development & Workshops
Beyond Black@ - Developing an Effective Communications/DEIB Partnership with Jan Abernathy
We're excited to announce the addition of a special workshop for Communications Directors
Join us on Tuesday, August 10, from 2:00-3:00PM ET on Zoom. Click here for more information and to register.
3-Hour K-8 Racial Literacy Curriculum Overview PD with Jason Craige Harris
Join us for an interactive 3-hour overview and in-depth discussion of Pollyanna's free K-8 Racial Literacy Curriculum. This session is a great introduction for faculty/admin or for new faculty/admin if your school has already implemented the curriculum.
Saturday, August 14, from 1:00-4:00PM ET on Zoom. Click here to learn more and register.
Showing Up and Standing Up: A 5-Part Journey Towards Antiracism for White Adults with Jay Golon & 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, 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
New Schools & Organizations Working with Us
Welcome to: ACCEPT Education Collaborative, MA; Gaston Day School, NC; Patterson Park Charter, MD and Wellan School, MA.
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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