From the Head of School

By Jamie Williamson Head of The Windward School

In an ultraendurance bike race—when I’m pedaling for 10 or 11 hours—it’s not a question of whether I’ll hit a mental or physical wall; the question is, “How many walls will I hit?” And how am I prepared to confront those walls, to overcome them, to get myself in the right headspace to continue? One of the most formidable items in an endurance athlete’s toolkit is not only to anticipate these walls, but to embrace them. Acknowledging that there will be pain can be incredibly empowering, because it allows for both confronting that reality and maintaining unwavering faith that the challenge is surmountable.

I’ve been thinking a lot about this concept lately, which Jim Collins described in his book Good to Great as the Stockdale Paradox. Named after Admiral Jim Stockdale, held in a POW camp for eight years during the Vietnam War, it describes the duality of simultaneously facing the brutal realities of the situation while knowing without a doubt that you will ultimately prevail. This concept has never seemed timelier and more critical, as our community navigates tremendous amounts of stress, trauma, and ambiguity. Blind optimism alone cannot get us through this, nor can pessimism. In a moment with no right answers, we have only a clear direction forward to serve our students.

Serving our students entails making the sacrifices that we know will keep them safe, such as social distancing, wearing masks, and changing our behaviors. It includes listening to the science and accepting that, even with the vaccine, we have a long way to go. Equally important is having the discipline to model compassion and recognize that we are all struggling. Giving each other a little grace, seeking to understand one another’s perspectives, is invaluable. We’ve all been impacted by the current health crisis in different ways, and as we’ve come to realize, there is no onesizefitsall pandemic.

Witnessing how our community has risen to the occasion with strength and resiliency to meet this moment has been aweinspiring. It is clear that many of us see this period as an opportunity to do better, to be better, and to persevere with the faith that we will get through this. I know that we will look back on this time and feel a great pride at how we handled this challenge and how we all rallied to support our students. I have never been prouder of a community in my entire life.

Thank you for all you have done, and continue to do, to ensure that our students feel supported while they face unprecedented changes and difficult realities. They are watching the example we set, and they are learning valuable lessons about overcoming adversity. These daily disciplines, both the drive to consistently improve and the belief that nothing is insurmountable, will serve them well long after they leave Windward.

Here’s to our collective continued endurance.

Jamie Williamson Head of School