From the Head of School

By Jamie Williamson Head of The Windward School

Lately, our community—and our society as a whole— has been existing in a state of paradox. On one side, we are reckoning with more than two years of real loss, of upheaval that has presented the challenge of our generation. On the other side, there is a palpable sense of hope, of possibility for the future, as we gradually resume connecting with each other in person. In the process of enduring hardship and emerging from it, how do we ensure that we hold space in our hearts for both the sorrow and the joy?

These seemingly contradictory states of being are inextricably linked, and we cannot fully experience one without the other. As Brené Brown noted aptly in an episode of her podcast Unlocking Us, “Hope is actually a function of struggle. People with the highest levels of hopefulness have experienced, embraced, and understand struggle.”

Our Windward community embodies this concept in a way that can only come from authentic experience. As parents/guardians and educators of children with learning disabilities, we live this reality daily, that of struggle and of hope. But it has certainly been heightened in the last couple years. Some members of our community have experienced unfathomable loss, while others have experienced major changes to their work and their home lives. Yet, we have still shown up for each other, for our students, and for our teachers.

The paradox of struggle and hope, of them coexisting simultaneously, is what creates the resilience that is the hallmark of our community. We witness it in our students regularly, this tenacity that drives them to continue to put in the work, to keep striving, to practice new skills again and again until they master them. It is a resiliency born of struggle.

Sometimes the kneejerk reaction can be to compartmentalize emotions around struggle—to pack away these feelings of discomfort, to not acknowledge them when we feel them within ourselves or see them in others. I know that I can tend to do that, to compartmentalize, and I always notice when it’s happening. In these moments, I feel out of balance. But I’ve found that when I lean into this discomfort, when I “face into the wind” instead of turning my back to it, it gives space for those around me to acknowledge their own struggles and be vulnerable.

Embracing vulnerability becomes a catalyst for growth, because it signals a desire to remain open to change, to expand our perspectives, both of ourselves and of one another. We cannot expect our students to lean into this mindset unless we model it for them. We cannot expect our faculty to do this unless leadership models it for them. We cannot expect our children to lean into growth if we’re not willing to do that work ourselves.

As we’ve seen in our community, when this level of trust is born, when we are truly connected, it can be transformative. I have a great deal of gratitude for our community, for its willingness to hold its members close throughout difficult times and for its willingness to step into joyful moments worth celebrating, such as the return of a joint eighthgrade graduation ceremony, the first time in three years.

Honoring the balance between acknowledging struggle and embracing possibility is at the heart of what we do. It is the reason we feel such a sense of urgency in the work we do, and it is what gives our work meaning. We only need to look to our children to see how powerful it can be to achieve this state of balance.

Jamie Williamson Head of School