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You Can't Go Home Again...Unless It's to Your Brentwood School Family
Billy Kaplan '04

When people ask me, often skeptically, why I’d want to teach at my alma mater, the only honest answer I can give is that Brentwood is the only place I ever really envisioned myself teaching. 

Sure, for some, the mere thought of returning to the site of in-class essays, teenage angst, a less than stellar complexion, not to mention embarrassing fashion choices, could be enough to induce panic so severe you’d think you’d been transported back to your Billy Budd presentation. 

Truth be told, though, I had a hunch I would be back at Brentwood one day. Once it dawned on me sometime in college that the reason I could never decide what I wanted to do with my life beyond school was that, for me, there was no “beyond school,” I realized I needed to find my way back to a high school setting. 

I moved to Washington, DC after graduation and joined a yearlong service program that would place me in a charter high school. There I got my first look at schools from the “other side,” seeing just how much went into shaping the student experience. I spent my first year planning afterschool programs and facilitating tutoring sessions for the students, and I became a full-time math teacher once my volunteer year ended. 

With no real formal training, believing fully in the half-truth that the best way to learn is to throw yourself headfirst into the mud, I relied heavily on my own experiences in high school math classes to guide me through that first year. WWTD? (What would Ms. Torre do?) How would Mr. Svec explain this? Am I baking enough cookie cakes? Did I do the quotient rule dance right? 

In some ways, I was faking it until I made it, but in others, I knew I could trust that the model that had inspired me as a student for six years at Brentwood would inspire the type of teacher I hoped to become. 

I knew I could trust that the model that had inspired me as a student for six years at Brentwood would inspire the type of teacher I hoped to become. 

As I navigated my first few years of teaching in DC, I often relied quite literally on my Brentwood teachers, keeping in good touch with Ms. Torre. She’d give me advice about how to communicate different nuances in the classroom and, especially as I began teaching some high-level geometry classes, would even send over some of the materials she’d created in her forty-plus years of teaching. 

When I found myself sick of DC weather and spending all of my spring breaks in LA, I decided it was time to come home. Of course, Brentwood was the preferred destination, but until a job opened up, I’d need to take a detour. 

In my third year back in LA, teaching at Milken, I got an email from Ms. Torre asking if we could talk by phone. She told me that she was thinking of retiring and wanted to know if I’d be interested in taking over for her when she did. Trying to hide my true excitement, I faked some professional reply about “how I’d be interested in exploring further the possibility,” deep down knowing that I’d start the next day if I could. 

After a few interviews and a model lesson, I was offered the job and, if I recall correctly, accepted it the same day. I would not only be teaching Honors Geometry, my favorite class I took at Brentwood, but would also become a ninth-grade dean. I so distinctly remember how the deans shaped student experiences and I was so excited to add that to my role at Brentwood. 

Having now been back for almost a full school year (which seems crazy as I write this), I can confirm that you really can’t go home again. Now while this adage might connote negatively, I do not mean it so. Rather, while being a teacher at Brentwood is vastly different from being a student (no more sleeping in on late days, no more dots at the snack bar, etc.), it has been a remarkable experience. 

I’ve gotten to work with my own former teachers, to see how the school has grown and will continue to do so, and to add my own flair to the place that inspired me to do what I do. Besides, it is awesome to pass daily the fields where I once dominated (a little revisionist history never hurt anyone).

Billy Kaplan is back in the Brentwood classroom—this time as an Upper School math teacher. Brentwood School yearbook photos from 2004 and 2019 reflect Kaplan’s sunny nature.

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