
08 Nov What Does It Mean To Be You? Reflections on the Pollyanna Conference
Reflections on the Pollyanna Conference
Creating spaces where everyone feels they belong is not just a professional duty—it’s a deeply human need.
– Janine Jones, Assistant Head of School for Community and Belonging
The eighth annual Pollyanna Conference, held on October 19, 2024, brought together 28 independent schools for important conversations around diversity, equity, and inclusion.
This year’s theme, Exploring Gender in 2024 and Beyond, focused on how we can better support students in expressing their true selves and building a more inclusive school environment.
The day provided a valuable opportunity for reflection and shared learning about identity and belonging.
As a facilitator for one of the Parent High School Conversations, I had the honor of participating in discussions about the evolving nature of gender and how we, as parents and educators, can support students more intentionally.
A key takeaway was the importance of allowing students the freedom to define themselves without the limitations of society’s expectations.

Lily Zheng, a sought out diversity, equity, and inclusion consultant, delivered a thought-provoking keynote that encouraged us to reflect on how we engage with students and their identities.
Lily centered the talk around two essential questions:
What does it mean to be you?
and
What do you need from me?
These questions served as a framework for thinking about how we can listen and provide meaningful support to students on their path to self-discovery.

Lily shared personal stories, including one about a teacher who, while supportive, made a comment about Lily’s handwriting not being “feminine enough.”
This remark, though small, had a lasting impact, highlighting how even well-meaning comments can reinforce limiting gender norms.
The best way to support gender nonconforming students isn’t to police them,`` Lily said.
It’s to stop policing ourselves. Let’s expand the boxes we put people in and let everyone grow into who they’re meant to be.
Lily emphasized that supporting gender inclusivity benefits all students, not just those who are trans or gender nonconforming.
Inclusivity isn’t just for trans and gender nonconforming students,`` Lily noted.
To truly create an inclusive environment, we need to break down the boxes we’ve put everyone in, including cisgender people.
This broader understanding of inclusivity encouraged us all to think about how we can create more space for individuality and expression.
Lily left us with four practical steps for building a more inclusive and supportive environment:
- Expand the box, don’t limit it.
Allow students to explore their identities without forcing them into narrow categories.
When we make space for different expressions of gender,” Lily explained, “we create an environment where growth is encouraged, not restricted.``
- See students as they see themselves.
Respecting a student’s chosen name and pronouns is a simple but powerful way to show that you value their identity.
If they trust you enough to share their truth, it’s your responsibility to honor that trust,” Lily said.
- Focus on well-being, not outside noise.
With so much external discussion about gender, it’s easy to get distracted. Lily reminded us that our focus should always be on students’ safety and well-being.
The media can talk all it wants, but our priority should be ensuring students feel safe, respected, and supported.
- Commit to ongoing learning.
The understanding of gender is constantly evolving,” Lily said.
As educators and community members, we need to stay open to new perspectives.
This commitment helps us grow and better support our community.
These steps offer a clear path for creating a more compassionate and inclusive environment at Harvard-Westlake.
As we reflect on this year’s Pollyanna Conference, the importance of creating a space where every student, teacher, administrator feels seen, respected, and valued is evident.
It’s not just about discussing inclusion—it’s about taking actions every day that reflect our commitment to it.

A special thank you to Janine Jones, Assistant Head of School for Community and Belonging, Dr. Jon Carroll, 9th Grade Dean, Student Leadership Teacher, and Middle School Diversity, Equity, and Inclusion Coordinator, President Rick Commons, and Head of School Laura Ross for their leadership and support in making this year’s Pollyanna Conference so meaningful.
Your guidance and openness to create an inclusive environment have made a wonderful and significant impact on all of us.
Thank you for imagining a future where we can move forward together.
With gratitude and awe,

