From the Head of School

By Jamie Williamson, EdS Head of The Windward School

“Human connection is being fully known and fully loved.” This perspective, shared by Dr. John Delony, applies both to our closest relationships and to those within our community. I would add that, to feel fully known, we must feel comfortable embodying our real selves, without filters, without edits, and without concealing those aspects of ourselves that we fear others may not accept. Dr. Delony continued, “We [can tend to] live in the shallow end of our relationships, afraid to go deep because of the potential consequences.”

When we talk about our core value of Community at Windward, we mean it in the true sense of the word: We believe in fostering a culture where everyone feels valued and that they belong. Diving into the deep end in our relationships involves embracing vulnerability, engaging in open dialogue, and approaching our differences with curiosity and an eagerness to learn about one another. It can feel risky, sharing with others that which makes us unique, but it’s the fact that it feels frightening that makes it ultimately so rewarding when true connections are made. Having the courage to lean into the messy, complicated work that truly authentic relationships demand is not an easy endeavor. But as Brené Brown has aptly stated, “You can choose courage, or you can choose comfort, but you cannot choose both.”

As we’ve been engaging in our DEIB efforts, the primary goal has been for every single member of our community to experience a profound sense of belonging at Windward. We have been intentional in this work, holding the firm belief that we cannot fulfill our mission as a school without addressing diverse representation, without advancing equity, without promoting inclusion, and without nurturing belonging. Real, lasting progress is possible, and it involves taking a close look at what we are doing, what we are not doing, and what we can do better. While we have made great strides in the last few years, we acknowledge that there is much work to be done, and this is a journey, not a destination.

I’ve noticed that the word “tolerance” is often used in the context of conversations around diversity, equity, inclusion, and belonging; I find that it falls short in expressing genuine intentions around these efforts. Tolerance frequently has a negative connotation, as evidenced by its common synonyms: “put up with,” “endure,” and “stomach.” Tolerance is certainly preferable to intolerance, but what if we were to move beyond tolerance—to acceptance and, ultimately, to understanding? Windward’s Director of DEIB, Dr. Romina Pacheco, posed this question recently, and it represents a compelling concept that merits lifting up within our community. If tolerating something connotes “putting up with it,” accepting something takes it one step further, toward affirming it. Only then can we move even beyond acceptance, toward seeking understanding.

Bringing our collective voice to honoring our diverse populations, cultural backgrounds, and lived experiences involves not only acknowledging but celebrating our differences. Every student at Windward deserves to feel truly seen, in their curriculum, by their teachers and administrators, and by their peers. As Windward’s leadership team has reviewed the School’s calendar, for example, we have given careful consideration to including cultural heritage months, days of recognition, and celebrations that accurately reflect our interdependent world, with the goal of preparing our students for responsible citizenship. In this issue of The Compass, Dr. Pacheco expands upon the concept of seeking understanding of one another in her article, “Bridging to Reach Understanding” on page 6.

I’m incredibly proud of the work this community has undertaken around DEIB efforts, as it represents a true commitment to our core values, our mission, and our vision of a world where every child with a language­based learning disability is empowered to achieve unlimited success.

Jamie Williamson, EdS Head of School and Executive Director of The Windward Institute