“Shared knowledge is the best knowledge,” Jessica Lee reminds her ninth grade English students. In a morning class, she cheerfully roams her classroom in the Inlustrate Orbem Building, laying out the fundamentals of the Upper School English curriculum, from grammatical terms to literary interpretation, but regularly having students work together in small groups. “Anybody have any brilliance at their table they want to share?”

Lee, who began at Latin three years ago, became Chair of the Upper School English Department this summer; she brings the same passion for collaboration to her peers that she imparts to her students. Only a couple of weeks into the school year, her students are comfortably bouncing ideas off each other and reading passages to each other.

On this day, Lee shares the macabre 19th-century version of “Cinderella” written by the Brothers Grimm — “Why the heck would we put that in front of children?” she asks the class, leading them into a conversation about fairy tales as moral instruction. Above all, she’s teaching these freshmen to be perceptive readers and active commentators on literature. When she asks for a gloss on a passage in Sandra Cisneros’s novel The House on Mango Street, there’s only murmurs, although some of them are perceptive. “I heard somebody whisper,” Lee says with a smile, “but it wasn’t confident enough for me.”

How are you a better teacher now than when you started? 

When I started, I was so insecure. Teaching is such a vulnerable artform, and when you’re young, you have such a big imposter syndrome. Now I’m confident in my ability not to know everything: when I admit that, it allows me to be much more responsive in my teaching, which encourages these authentic connections with students. There’s a poem I love to teach, “Bluebird” by Charles Bukowski. Last year, we were talking about a word choice in it: I was sharing my point of view, but a student had the wherewithal to say, “I actually interpret it a different way.” Now in my career, I celebrate that: I’m happy to throw out everything I was planning to talk about, because that difference of opinion is really beautiful. It’s wonderful when students realize that their interpretations are valid and that they might be seeing something that their teacher missed.

Do you have a favorite book to teach?

The Kite Runner. It’s become a cornerstone for the ninth graders: the stuff that Khaled Hosseini is doing is so interesting and rich, with parallel structures and flashbacks and callbacks to dreams. It really resonates with kids: when they read it, I can see them blossoming. With my AP class, it’s a tie between The Stranger by Camus and As I Lay Dying by Faulkner. It’s fascinating to watch them grapple with Faulkner; it’s a literary badge of honor.

Is there value in teaching books that are just outside the reach of students?

I think that’s when they do their best work and that’s when they need us. When I started teaching, there was a push to incorporate young adult literature: every ninth grade classroom was reading The Hunger Games. There’s something lovely about kids just reading — but there’s also something special about them encountering a roadblock or a moment in a book when they know instinctively that something important is happening, but they can’t quite articulate why. To me, that’s the value of the classroom space: somewhere they can work through those moments as a community.

What were you like in high school?

Type A: very little sense of humor and very little flexibility. It’s one of those things that I’ve grown out of.

What’s something you’re good at outside of your work at Latin?

I am good at completely derailing a conversation. If you ever want a non sequitur, I’m your girl.

Tell us about a moment in your life that required courage. 

Coming to Latin three years ago, leaving behind CMS after 11 years. At CMS, I was a leader and I had a reputation. My imposter syndrome came back at Latin when I joined the juggernaut of the English office. Not only does everyone here care and want to do the job — everyone is brilliant and has these deep areas of expertise. 

How does the English department work together?

We have these constant moments of reckoning and awakening: what is it we believe and why? Over the summer, we worked collaboratively to develop style guides. We would have conversations about something as simple as What do we call the line of argument in a thesis? Do we want to call it a claim? A sub-claim? A topic sentence? And why would we make these distinctions  and why do they matter? This department commits to those discussions with so much intentionality and purpose: you can’t even have a casual conversation without somebody saying something profound that you have to think about for three to five days.

I also got to sit down with our senior seminar teachers about the courses they were designing: it was wonderful to see everybody inspired. Erika Thurman was talking about the roleplay project in her fantasy literature class; Richard Harris was planning how his students would adapt literary works as short films; Alan Becker was talking about having students designing a dystopia but not making it current events. I’m so grateful to Latin for nurturing and embracing those creative pursuits: not only does it empower us, it gets our students excited.

What aspect of the Portrait of the Latin Leader resonates with you?

I’m constantly circling back to Humble Collaborator and aspiring to it. The work doesn’t have to be on a marquee to be effective and good. And sometimes you have to put your own needs aside for the collective to attain something better — that resonates with me, especially in my time as chair. 

What are the rewards of teaching a student more than once?

That is something I’m so excited for: next year, the seniors will be the freshmen that I taught my first year at Latin. I’ve told people that I need one more year with AP Lit and then I’m willing to give it up to anyone in the department who wants it. But I’m excited to get the band back together — these students will be able to approach literature with such a different level of depth than when they were ninth graders. You know what works for those kids and maybe where they’ve had struggles, and the trust is implicit. Even having a few pockets of kids you’ve taught before lets you lean into deep conversations so much faster, so you can get into the actual joyful work of the classroom.

What’s your favorite day of the school year?

Sunny’s Day. It’s fantastic to see our community come together, with the Lower School and Middle School and Upper School engaging with each other. The Lower School kids would completely idolize our Upper Schoolers, and the older kids would discover in real time that people looked up to them: you matter and you are a leader. It was lovely to see them recognize that in themselves, some of them for the first time — they had control of how this day would go for other people.

What’s the last great book you read?

Tender Is the Flesh, by Agustina Bazterrica. It’s about society turning to cannibalism when other types of meat become diseased. It’s so powerful and visceral — I would make it through 20 pages and then have to put it down for a day or two. If you’re looking for a beach read, I recommend Yesteryear, a witty psychological thriller by Caro Claire Burke. 

What’s something you used to believe that turned out not to be true?

I used to believe that life was black and white — I’ve become much more open to the idea that conflicting realities can both be true. That’s helped me accept things as they are, even if they don’t seem to make sense. That’s the core study of literature, too: looking at unfamiliar experiences and finding the humanity in them, even when it doesn’t initially feel true. It doesn’t require catharsis, just having no expectations other than understanding a little bit more than when you started.