Head of School’s Notebook: Free Days

December 7, 2022

I have worked at three different schools in my lifetime and attended three others from elementary school through high school. Each one had its own unique character, but all had a single similar tradition: free days.

They weren’t called the same things in each place. At St. John’s in Houston, Texas, where I worked prior to coming to Cate, any randomly called day off happened on Mrs. Mulligan’s Birthday. Mrs. Mulligan allegedly ran a doughnut shop near the school years ago and whenever she was inclined to play hooky she put a note on her shop door, “Closed on account of my birthday.” Apparently she had several birthdays a year, which is how everyone caught on.

The folks at St. John’s borrowed the idea from her. At Westminster, where I went to boarding school, we had “Hill Holidays.” Not quite as interesting a name – the school is on a hill – but the energy behind the tradition was no less captivating.

I remember sitting at formal dinner in the fall of my first year at Westminster and hearing Mr. Werner, our Head of School, announce a Hill Holiday. It was near Thanksgiving and I was feeling the strain of a long fall. I’m not sure – even to this day – I can capture the range of feelings I experienced in that moment of announcement. Surprise, relief, elation, even a little disbelief. Could something this wonderful really be happening?

On Monday night, I watched as the entire Cate student body went through the same range of emotions and reactions. Elan Halpern ’16, crypto expert and all around amazing human being, was here to deliver a convocation. She was masterful, of course, especially at the end when I asked Elan, “What is the one thing that you wished you’d done at Cate that you never got to do?”

After a well-timed pause, she said matter of factly, “Call a free day.” Bedlam ensued in Hitchcock Theatre.

It is quite something to see all that exhilaration on a Monday evening. There were tears and cheers. Raucous applause. Lots of hugging. Students kept coming forward to thank Elan, some of whom seemed pretty overwhelmed with gratitude, not simply for her convocation but for her part in their windfall. It was lovely and delightfully genuine.

There were a number of alumni present for the talk as well, and they noted afterward their memories of the very moment they were watching unfold. “There is something about the sudden reprieve of a free day that is hard to describe,” said Trey Jackson ’16. “It’s so much better than a planned day off.”

Indeed, it’s a gift of the rarest kind: a gift of time.

And this is the season of giving. Perhaps there is some irony in a Head of School appreciating the opportunity to call off school. Many – both students and faculty – have suggested I do so far more often. Fair enough.

But part of the value of the free day comes – in keeping with Elan’s talk on crypto – as a result of scarcity. The moment is special in part because it is so rare. That’s a convenient rationalization for a Head of School, I suppose, but rare doesn’t mean non-existent. I still have a few more free days in my pocket to use between now and the end of the year. And like the rest of this community, I intend to savor each moment, free day or not, for the gift that it is.