“Yo Jay, yo Jay, check this out!”

We ended the drive with the five of us singing “You Make Me Feel So Young,” a swinging tune that sums up at least a part of my swirling emotions as principal at San Dieguito. Four amazing students, creative, funny, and kind, had asked me to shed any administrative dignity I might have and join them for Carpool Karaoke. “Yes” was the right answer, and by the end of the ride the lyrics to that Sinatra song had never been so true.

2Being a principal means being willing to play, participate, and share laughter with students. It also means shouldering responsibility, working hard and sometimes long hours, and bringing as much balance as possible to the job. Keeping students first in my mind helps me do that.

So today, as ASB kids filmed a segment for the spring assembly, I hopped into a car and did my best to destroy a series of marvelous songs.

They’d asked me if I had anything I wanted to sing, and before I answered I thought about it, only to realize that the music I listen to falls into two categories: old, old, old stuff (Sinatra, Billie Holiday, Ella Fitzgerald, so out of their world as to be unrecognizable) and rock and roll not suitable for a principal to croon (let’s be honest, it simply isn’t appropriate to hear the principal sing almost any song by Prince, The Pogues, or Social Distortion). So I made only one suggestion, an unexpected ditty that I thought would be worth a laugh, and I left the rest of the playlist up to the students.

3We started innocently enough, with a little Bowie. Parking is an ongoing challenge at our school, so we set the narrative of our video as my helping the driver, a senior, find a place to park. There was no more natural soundtrack than us mm-ba-ba-de-de-bum-bum’ing our way through Queen’s “Under Pressure.”

We laughed, anyway.

Next, I revisited my misspent youth with an unexpected riff on Run DMC’s “Son of Byford,” my driver beat boxing as he shook his head that this old man would know the words of any rap song.

The Sugarhill Gang’s “Rapper’s Delight” did not go so smoothly, but by the time we belted out “The Time of My Life,” a fitting farewell to SDA, we’d both hit our stride.

4Half an hour later, thinking we had enough footage to be cut and spliced into at least 30 seconds of entertainment, we headed back to the front lot. As we did, laughing that there might be no songs that we both knew the words to, we picked up three ASB students who were helping film and edit the video. They piled into the back and I apologized as we pulled away from the curb. “I only know Sinatra songs,” I said, and from the back seat I heard: “Pull over.”

Then, with a quickness that surprised me, my driver found a series of Old Blue Eyes songs on his phone. From the back seat came the suggestion for “You Make Me Feel So Young,” and without hesitation we broke into song.

I don’t know if the cameras were rolling as we drove back to my office, but I do know that those two minutes will remain in my memory as some of the most joyful I’ve had here at San Dieguito.

1I’d thought that my choice of Run DMC would be the biggest surprise of the day, but (as is so true so often at this fabulously funky school) it was the students who surprised me. They were so kind to invite me to join the fun, they put up with my inability to sing, and they even knew a little Sinatra. A delight.

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