Ping! Jill Flynn hits a chime with a small mallet and her fifth graders focus: they know it’s time for math. She walks around her classroom, helping the students who are having trouble and encouraging the ones who are working through the thorny issues of denominators. “You caught your mistake,” she tells a student. “Now go ahead and fix it.” At this moment, she’s an upbeat Lower School coach in her element, helping kids to do things that they didn’t believe they knew how to do when they arrived at school that morning. “You did the hardest part,” she encourages another student. “We'll practice more today.”

What are the challenges of teaching fifth grade?

Some kids are solidly fourth-grade-young at heart; other kids are ready to move on to Middle School and be a tween who doesn’t want to see Disney movies anymore. So you need to make sure they can coexist. Even the tweens who are ready to move on, they’re not that old, but they have an intense awareness of what is everybody else doing? So they’re uber-sensitive to what other people are wearing, what they’re scoring on tests, what they’ve done over the weekend. Parents are diligent about not letting kids have a lot of access to social media, but you’ll see some experimenting with technology at home.

So what do you do to make that classroom culture work?

Just raise uncomfortable topics with them. The kids want somebody to help them: “This person used to be my friend and now they’re not being nice to me. How do I navigate that? What if I don’t like going to sleepovers or I don’t like hanging out at the mall with other people? Is that normal?” It’s friendship, it’s deodorant, it’s worrying about tests. 

Do you have a favorite subject to teach?

Math. We’re leading up to pre-algebra skills, so our focus is on problem-solving. We’re solidifying all the operational stuff like adding, subtracting, multiplying, and dividing, but also doing that with fractions and decimals. I was an accounting major in college, so I love math, but I see that kids either love it or hate it. And if you don’t like it, you automatically say you’re not good at it. I like the challenge of making sure that they recognize that they’re good at math even if it takes them a little longer. When you get older, your boss is not going to say “You better solve this algebraic equation in two minutes—and if you don’t, you don’t get your bonus.” What I care about is did you attack the problem? Did you find a strategy? Were you successful using your math knowledge? It’s fun to see the kids get there.

Do you have a favorite fifth-grade tradition?

Other than our moving-up ceremony? We have a kickball tournament every year. It’s for fun, but it can end up being a huge lesson: it’s often not the team with the best athletes that ends up winning. The athletes try to control the game and so they’re not playing as a team. When the kids who aren’t as athletic end up winning, you see this pride and joy because they didn’t think they could do it.

How did you end up at Latin?

My kids came here first. When we were looking at kindergarten, we checked out all the local schools and Latin was on the top of our list. It obviously offered a stellar education, but we were also attracted to the balance of athletics and arts. All three of our kids are Latin Lifers: Jessica, who has graduated from college; Lindsay, who’s at Michigan; and Matthew, who’s a junior here. 

Then, when the kids were the right age, I wanted to go back to work, but not at the bank—I had been a manager in the operational division. I worked third shift, I worked second shift, I managed customer service, but I had always wanted to be a teacher. I was scared to death, but my husband encouraged me to go back to school and get a master’s degree. One of the things I quickly noticed was that I could tie it straight to what I was doing in the business world. I had employees at the bank — I had to help them through their issues — and here I have students. It’s the same idea, just in a different environment and with a different goal.

What’s the best advice anyone ever gave you?

When I was going to college, my dad said, “Go wherever makes you happy. Pick a school that you feel comfortable at and don’t worry about where everybody else is going.” As an 18-year-old, you appreciate that because you’re trying to make everybody happy and you don’t know what you want to do yet.

Do you have any hobbies?

I would say my hobby is music. I can kind of play the piano, but I love concerts. One of my favorite ones recently was all the old people: Loverboy and REO Speedwagon and Styx. I didn’t realize how many Styx songs I knew.

What are the fifth-grade teachers like behind the scenes?

When there are no students on the hallway, we like to scare each other. One of the funniest things we did last year was have a teacher hide in a closet and then jump out to scare another teacher. We also do food challenges at lunch: frozen pizza taste tests or we did a Pop-Tart challenge where everybody had to bring in one of the new nasty flavors. The kids don’t see us doing those things, but they see the camaraderie that results — laughing and having fun and teasing each other in a polite and respectful way — and I think it’s helpful for them to see us modeling appropriate behavior that way.

What phrase do you say all the time in the classroom?

“No stress.” They come in with this anxiety about fifth grade. I tell them that every year is going to be new, so it’s going to feel hard, but it isn’t going to be harder than any other year and we’re going to do it all together.