August 2023 Update from Pollyanna
August 2023
Dear Friend,
Even though the challenges facing us or our society never take a vacation, summer still feels like the most reflective part of the year. Maybe it’s the heat (or, in the case of this summer, the extreme heat), but I have always felt like things slow down just enough in summer for important, focused thinking. One question that has inspired a good deal of reflection in recent weeks was posed in one of my favorite newsletters by Sahil Bloom:
“If I repeated this day for 100 days, would my life be better or worse?”
I love this idea. It forces me to look deeply into my day for all the highs and lows; all that for which I’m grateful and all that I’m trying to change for the better. When I’ve asked myself this question recently, I keep coming back to three different personal reflections:
  • My son and his partner of seven years became engaged. It wasn't a big surprise and yet it is a time filled with so much joy and hope. When the future of our country and world seem precarious, knowing people still believe in a future is very hopeful. No date set or place chosen, but we are...hopeful.
  • I’ve thought about loss; recent loss and the losses that always stay with you. David Trower, the head of school I worked for at The Allen-Stevenson School for 18 years, unexpectedly passed away last month. He gave over 30 years to A-S and I only wish he had more time to enjoy his retirement. This August also marks the seventh anniversary of my mom’s passing. She left before so many highs and lows took place in our family and the world. She is a loved mom, gram and friend, and she is very missed. I’m always amazed at how much people who are no longer here continue to influence day-to-day life.
  • Pollyanna turns 8 this year and we are finally celebrating our 5th anniversary three years late! Three years ago, I would not have been sure this anniversary would happen, and am happy to say we’re here and thriving. We are celebrating all year with conferences, workshops, assessments, and Teen Council meet-ups. (Join us for one or more!)
The point is: Even though this summer has shown us fires devastating many parts of our world, SCOTUS rulings that will wreak havoc for generations, migrant families treated so inhumanely, and a country that’s banning books and rewriting history faster than imaginable, I would still choose this day to live over and over again.
Why? Because finding joy, making time for friends and family, and stepping up to address the challenges of our world are more than enough motivation to get out of bed each morning.
Thus, my answer to Sahil’s question is an emphatic “Yes, I would live this day 100 times over again.”
I hope you’ve had many opportunities to find the bright spots on any given day that are worth repeating over and over again, as well as the meaningful challenges that inspire us to do the work of change each and every day. 
Casper Caldarola

In the News

THIS WEEK: Jason Craige Harris
Join educator, facilitator, mediator, and restorative justice practitioner Jason Craige Harris for, “Toward Accountability and Repair: On Navigating Race, Harm, and Shame.” In this workshop participants will learn the basic tenets of restorative practice, fresh ways of thinking about harm and repair, strategies for addressing “little” harms that threaten to escalate, and interventions for navigating complex harms. 
Thursday, August 3, 1-3 PM ET / 10 AM-12 PM PT
NEXT WEEK: David Smith
Join David Smith, Director of Advancement at Saint Ann’s School, to learn how to create a more inclusive advancement program, build greater connections between DEIB and advancement, and elevate the cultural competency of your advancement team and operation. 
Thursday, August 10, 1-2 PM ET / 10 AM-11 AM PT 
NEW: Ivy Alphone-Crean
Join Ivy Alphonse-Crean for this newly added workshop. We will look at specific tools to use in the classroom for students ranging from pre-k to 8th grade. Educators will come away with their own exercises to bring into their classrooms in order to promote a more mindful and inclusive learning environment.
Tuesday, August 22, 12-1PM ET / 9-10AM PT
NEXT WEEK: Jan Abernathy
Whether we are talking about "the work," using new-ish terminology to define gender, or simply identifying affinity groups, communications professionals are constantly being asked to normalize new language. Jan Abernathy, Chief Communications Officer at the Browning School, will show participants how to confidently frame, speak and write to the importance of DEIB and SEL initiatives.

Wednesday, August 9, 1-2 PM ET / 10 AM-11 AM PT  Learn more and register here

Jaqueline Nelson + Jay Golon
Join Jay Golon and Jacqueline Nelson, Pollyanna facilitators, teachers, and administrators with over 20 years of experience in independent schools, as they guide you through practical exercises and reflective discussions aimed at helping participants develop an “individualized engagement plan” for relationship building and community belonging. 
This workshop takes place over two days with two 2-hour sessions. August 15 and 16, 2023, 12-2 PM ET /
Melissa Mirza: Careers
Facilitator Melissa Mirza creates space for educators who identify as people of color to do some deep reflection on their next career move. Participants will map out what they want, how to get there, articulate their superpowers, and more!   
Wednesday, September 27, 1-2 PM ET/10 AM-11 AM PT 
Reach Out if We Can Be of Help with Your DEIB Planning
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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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