With the arrival of November comes the end of phase one in the college admissions timeline. It’s a good opportunity to reflect on a process that consumes so much of our attention and effort. For teachers, that effort involves writing recommendation letters. In mine, I always include an assessment of students’ academic achievements and potential, as well as insights into character traits like honesty, initiative, and empathy. But I am also guided by a remark from the filmmaker Billy Wilder: you are as good as the best thing you have ever done. When I write for a student, I search for that moment and feature it in my letter. I have no idea what impact it will have; I just think it is something an admissions officer should know. Over the past forty years, I have written countless anecdotes showcasing my students at their best. Among them, two stand out, and I want to share them here.
Years ago, a junior named Austin showed up in my American Literature class. In week one, I reviewed all the assignments for the semester. Along with the papers and tests, I included a list of practical tasks designed to help students relate to the literature on a personal level. For Thoreau, commit a modest act of civil disobedience. For Whitman, take a photo to capture his love of nature. And so on. As you can imagine, for the slave narrative of Frederick Douglass, I had a hard time thinking of something, but I eventually settled on asking students to fast for a day to simulate the hunger Douglass felt living on a starvation diet. As students looked over the list, I heard many of the reactions it had elicited from students over the years, including a few complaints about the inconvenience of fasting. Suddenly, a hand went up; it was Austin’s. In a tone that was both respectful and challenging, he asked if I really thought that fasting for a day could simulate what it was like being a slave.
The silence that followed was unlike any I had heard in all my years as a teacher. I looked down, collected my thoughts, and said no, it was an effrontery to think that. I also said that I was striking that item off the list. The moment passed without incident, and we all proceeded with the course. But that exchange stayed with me; you might say it put Austin in the role of teacher and me in the role of student. So when it came time to write his recommendation letter a year later, I included it in the final paragraph. Of course, I had no idea what impact it had, if any, on the admissions officers who read it, nor am I claiming credit for Austin’s acceptance, which arrived a month later. I only mention it here to recount one of my proudest moments at Pingry, and to affirm how lucky I have been to spend my career in a classroom.
The second story involves a student named Sophia. Unlike Austin, she never worked with me in any official capacity; we simply knew each other from conversations at my table in the hall. She was very studious and spent much of her free time in the library. As many of you know, my table sits directly across from one of the library stairwells. Occasionally, I would see Sophia descend the stairs from the library and head past me down the hallway. Over time, this happened frequently enough to pique my curiosity, so one day, I followed her to see where she went. It turns out she went to an empty classroom to help other students with their homework. I asked her about it, and she said it was a role she had taken on gradually: the more students she helped, the more students sought her out. This struck me as very altruistic, especially for a student who had an extremely demanding academic schedule.
A year later, Sophia applied to college. With no formal association, I was not in a position to write her a letter. But I had seen a Billy Wilder moment, and I wanted the admissions people to know about it. So I did one of the most unconventional things in my entire career. I found out where she had applied, and I wrote a letter; or rather, I told a story. As with Austin, I had no idea what impact the letter had, if any. To this day, I’m not even sure if what I did was ethical; it certainly was unorthodox. But I’m glad I sent it then, and glad I’m sharing it now. I’m not sure it’s the best thing I’ve ever done, but I would definitely put it on my list of top five.
Truthfully, I had some misgivings when I sat down to write this essay. Part of me didn’t want to share the stories with my readership. In some way, I felt I was invading the privacy of two former students, especially Sophia, who to this day does not know I wrote a letter on her behalf. Moreover, what about the flip side of Billy Wilder’s proposition: are we as bad as the worst thing we have ever done? That’s something I’d rather not contemplate here; maybe I’ll save it for another essay. In the end, though, I wrote this piece because I’m really proud of Austin and Sophia, and I hope their stories can serve as examples for us all. And finally, I want to acknowledge all the teachers, coaches, and advisors—educators all—who write recommendations for their students. Here’s to them, and the wonderful stories they tell.
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Author photo by Anthony "Truncs" Truncale '26
To contact the author: Mr. Keating