Head of School's Letter - January 9, 2026 - From Playgroups to Secondary School

Dear Families,

Most days, our eighth graders move through campus as they always have: confident, opinionated, vibrantly themselves. But lately, I’ve noticed a subtle shift. They seem especially attuned to one another, to the spaces they know so well, to the fact that something meaningful is drawing to a close.

This week, our Secondary School team completed the submission of applications and supplemental materials for our eighth graders. It’s a milestone that arrives quietly, without ceremony, but it carries enormous significance. Each application represents a child we have come to know deeply as a student and person. Their strengths, their growth, their hard-won confidence, their readiness for what comes next. I often think about how much of who they are can’t be captured on paper.

Today, in a much quieter moment, we also welcomed very young children to campus for an admissions playgroup. Some stepped right in. Others paused, hands tightly wrapped around a parent’s fingers, taking in the room before deciding they were ready.

That image stayed with me.

At very different points in their journeys, those children and our eighth graders are doing the same brave thing: standing at the edge of something new, learning when and how to let go.

What makes that possible, at every age, is relationships. The secondary school process at Brookwood is grounded in knowing students well and guiding them with care. Evan Diamond and Alli Moore bring extraordinary thoughtfulness and integrity to this work, advocating for each student with a keen understanding of who they are and where they will thrive. Their support is not about outcomes alone; it is about readiness, fit, and ensuring that each child steps forward with confidence and support beneath them.

By the time our students are ready to leave Brookwood, they carry far more than strong academic preparation. They carry a sense of self, an ability to reflect, and the quiet assurance that they are capable of what comes next.

As we move through these final months with our eighth graders, I feel a deep sense of pride in who they have become, paired with the awareness that this season carries weight.

Growth, even when it is joyful and right, always involves a measure of letting go.

And that, perhaps, is the work of a school done well.

Warmly,