Roquemore graduated from the school in 1987. After going to Howard with accounting as her intended major, Roquemore felt detached from the profession. She asked her grandmother for support.

“She told me to take an education class,” Roquemore said. “And I loved it. I loved figuring things out, connecting with people and helping people find their voice.”

After finishing graduate school with a master’s in Education with a specialization in Reading and Literacy, Roquemore spent five years teaching and working on program administration. She then took a six-year break to work as a flight attendant.

Once she returned to teaching, Roquemore came back “full throttle.”

She worked three part-time jobs in New York and started a full-time business in tutoring. She also ran summer programs and helped students with standardized testing. Seven years later, Roquemore’s daughter Zoe Olan (‘24) urged Roquemore to take a step back from teaching — asking Roquemore to be home at night.

Shortly after, Roquemore heard there was a position open at St. John’s. She applied immediately.

In 2013, Roquemore began her role as an Upper School English teacher.

“In a sense, it was coming home,” she said.

Roquemore had to learn how to adapt to the teaching environment, which she noticed was very different from when she was a student.

“I thought I had to be like the teachers that I had,” she said. “But the school was more diverse in thought. I had to shed some of those expectations and adjust to the place being more empathetic.”

Roquemore quickly integrated herself into School clubs. The first club she sponsored was The Black Student Union, formerly known as AAAG. When Roquemore attended the school, there were only 15 Black students in the Upper School. “I was really excited to be able to do something for the black students here, because I didn’t have that when I was here,” she said.

The following year, Roquemore became a sponsor for the Mixed Race Affinity Group.

“I was happy to take on that space too — to make sure the club didn’t flounder and that we had a place for mixed race kids to go and speak about their identity,” she said.

Roquemore also agreed to sponsor the Bible Study Club and Students Against Stigma Club. She headed the development of the Students Against Stigma Responder Program, where students gain awareness about navigating various mental health-based scenarios.

“Neurodiversity is a huge identifier that is neglected,” she said. “And I’ve learned a lot about that and dealing with mental health struggles.”

During her time at the school, Roquemore enjoyed how, even as a teacher, she was constantly learning.

“The school has allowed me to learn a lot and bring that into the classroom and share with faculty,” she said. “It’s been such a gift.”

Roquemore has also enjoyed the passion students bring into her classroom.

“​​The kids are so kind and gracious,” she said. “The students just want to bring their best generally, and it just helps me be my best.”

Two years ago, Roquemore had a feeling that the end of her teaching chapter was near.

“I took a breath. My family is in a good place, and now it’s a good time to step back and do something else for me,” she said.

Roquemore has one goal for her new chapter — to be intentional. While preparing for her leave, she made sure that the school was well-prepared. While colleagues were initially shocked, they were excited for her new journey. Now, Roquemore hopes to work with others to create innovation within education.

Before Roquemore leaves, she hopes to savor each moment.

“We have so many traditions that I just need to make sure I see everyone and have time with them,” she said. “Because next time I see people, it’ll be hard to find that quality time.”