Entering my third year as head of school, I find myself already musing about the next installment of a newly established tradition: our annual playlist. I am a great appreciator of music across all genres, which I attribute to a magical combination of factors—a father who considered musicology a parental responsibility of the highest order; my struggle with the clarinet in fourth-grade band, which instilled a lasting awe for those who can master an instrument; boarding school, which exposed me to eclectic taste from the world over; and a fervent devotion to friends and love interests expressed through the artform known as curating a "mix."

I experienced mix-making across two technologies: the cassette tape and the CD. A cassette offered a finite window—maybe 60 or 90 minutes—requiring careful planning for Side A and Side B. Where would the music come from? Did you need a dual deck to capture it from another cassette? Would you wait by the radio, poised to hit record the moment your song came on? How long were the pauses between tracks? How would you decorate the paper insert? When my generation transitioned to burning CDs, we became well schooled in patience, downloading music over dial-up internet. Even so, the ability to rearrange a playlist with ease felt like a genuine novelty.

I have been making mixes since grade school, and I remember the people who gifted them to me along the way. Knowing the effort invested in personalizing the selection—and the time dedicated to it—made each one feel truly special. Playlists, though they have evolved, still delight me. Spotify algorithms and AI prompt engineering have disrupted the artform, making it possible to generate a thematic song list in mere seconds. And yet—how wonderful that the Internet surfaces songs I would never have thought of on my own, or places them in an unexpected order. That said, I still enjoy the stimulation of doing it the old-fashioned way.

Which brings us back to the Fay faculty and staff annual playlist.

In my first year, our Adult Community Read was How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen by David Brooks, and our school-year theme was, fittingly, Seeing and Being Seen. I asked each Fay employee to submit a song that represented a slice of their life. The result was 7.5 hours of music, opening with DJ Jazzy Jeff & The Fresh Prince's "Summertime" and closing with Beethoven's Symphony No. 3 in E-flat Major, Op. 55 (Eroica). Last year, our summer reading was The Creative Act: A Way of Being by Rick Rubin, and our theme was Right Here, Right Now. I curated a playlist bookended by tracks of that name—by Jesus Jones and Fatboy Slim—and otherwise populated exclusively with songs produced by Rubin.

This year, Fay faculty and staff will be reading Junglekeeper: What It Takes to Change the World by Paul Rosolie, and our school-year theme will be The Power of Yet. So where do we go musically? "Welcome to the Jungle?" "Jungle Boogie?" Or do we embrace a growth mindset and look toward "Climb Every Mountain" and "Unwritten?" These are important decisions. I love being transported back to my own middle school years—sitting in front of my tape deck, trying to envision my listening audience.

We will need good music, because this year at Fay we are embarking on a strategic planning journey. The School is partnering with Tim Fish of Two Chairs Studios to craft a vision statement to accompany our mission and values, and to formulate a plan that cohesively articulates the community's priorities for the years ahead — in other words, to embrace the Power of Yet in imagining what might be possible. As we curate this metaphorical playlist, we will be seeking input from trustees, faculty, staff, parents, and alumni, thinking carefully about our audience: past, present, and future. The Board of Trustees will vote on the plan in May and hand it back to the School. With a year of preparation behind us and a successful kick-off at closing meetings this June, we are underway. Here's hoping we have just the right soundtrack for the year ahead.