At just 15, Reese Ratcliff is thriving at Groton School, a prestigious boarding school in Massachusetts. Her transition from Chicago City Day School — a private pre-K-8 school known for its close-knit community and dynamic curriculum — last fall felt natural thanks to the strong foundation she built.
“I grew up there,” Reese says. “I started when I was 5, in junior kindergarten, and stayed through eighth grade. It really feels like you’ve been with your family for a long time.”
One big benefit? “City Day did a fantastic job helping us manage all different aspects of school,” she explains. “By middle school, we’d grown into independent people.”
Here, Reese shares how City Day set her up for success at Groton, the skills she developed, and her advice for prospective Chicago City Day families.
Question 1: What’s one big way City Day prepared you for a competitive boarding school?
Reese: The writing program at City Day is just fantastic. By fourth grade, I was writing essays and creative short stories. In sixth grade, every week, we would be assigned a new prompt, like writing a scary Halloween story or recounting a time you went outside your comfort zone.
This definitely helped with my admissions process. I applied to seven boarding schools, which is quite a handful, and each one has three or four essays each. You’re really inspired to write new, compelling stories for each one.
Question 2: Can you share an example of a teacher at City Day who influenced you?
Reese: My theater teacher, Ms. Liza Batinich, was amazing. She has just been so encouraging and allowed us to reach our full potential while also respecting our boundaries.
I transitioned from being someone who had a bit of stage fright to doing an improv show. She always said, “This is your play. I’m just here to help.” That made me feel so empowered.
I’m actually taking a theater class in my new school now, and they want me to be part of the spring play. I totally credit her for that.
Generally, it’s always been easy to ask City Day teachers for advice. I felt like I could trust them, be open — and I was really respected.
Question 3: What was it like transitioning from City Day’s small environment to Groton?
Reese: It’s definitely different! Even though City Day is small, though, you don’t lack those social skills. The friendships that I built were strong, and that taught me how to branch out.
City Day also has so many unique people from all over Chicago. Now, I’m with students from 30-plus states and 20-plus countries. It’s so cool coming together to learn — and it’s something that really carried over from City Day.
Question 4: What leadership opportunities at City Day helped you grow?
Reese: In eighth grade, we ran the school store, called the Kuczmarski Co-Op, which sells school merchandise and gifts, and I was the manager.
Everyone is assigned a job — stocking, ordering, cashier and even marketing. We made posters and made it our mission to truly understand what the students wanted.
Overseeing the process and helping people work together allowed me to bring out others’ individual strengths, which is a skill I feel really helped me.
Question 5: What do you want parents or future students to know about City Day?
Reese: Everyone at City Day wants everyone to succeed. Teachers and students. And when you’re in an environment like that, it’s the greatest feeling, because people have got your back.
It’s definitely turned me into a person who values academics as an opportunity to learn, grow, and bond with people. You are pushed to your potential and surrounded by people who really want the best for you — and that is very motivating.
Content sponsored by Chicago City Day School, an independent private pre-K-8 school in Chicago’s Lakeview East neighborhood. Learn more at the Chicago City Day School website.
