Black students

Their Mom Always Said They Would Go to the University of Chicago, and That’s Exactly What These Twin Sisters Did

Growing up, Olivia and Aliyah Singleton frequently heard their mother’s prediction: “You’re going to go to the University of Chicago.” “I would just shake my head,” Olivia says. “I never thought I was good enough.” But they were. In fact, their academic journey eventually allowed them to view multiple facets of UChicago. The Singleton sisters spent most of their early years on the South Side of Chicago. Both were high academic achievers from the moment they started school. Even so, the twins didn’t necessarily feel a connection to the sprawling Gothic campus in their backyard. It didn’t seem like a part of their future. Before reaching high school, they had attended eight schools in Chicago and its suburbs. During their high school search, they learned about a charter school affiliated with that prestigious university down the street. The Woodlawn campus of the University of Chicago Charter School, known to students informally as UCW, would become their academic home for the entirety of their high school experience. “It was the longest we had ever stayed in one school,” says Aliyah. Their experience at UChicago Charter would prove to be highly influential. “When I entered high school, I wasn't comfortable in my own skin,” Olivia recalls. “Being a Black little girl with ambitious dreams, I had a history of getting shot down quickly by a lot of people. It was hard.”

‘The principal and teachers made me feel seen.’

UCW, which serves predominantly low-income Black students, celebrates Black history and culture and works to develop critical thinkers and leaders who are culturally aware. This focus was invaluable to both sisters. “Until high school, I would rely on my twin sister to be my mouthpiece,” Aliyah, the older and more reserved sister, explains. “UCW helped me grow as an individual. I learned how to find my own identity, build relationships with teachers and other students and, especially, take pride in my Blackness.” Olivia agrees. “The principal and teachers at the Woodlawn campus made me feel seen. [pullquote position="left"]They showed me what it meant to be a great student and to have pride in that. It drove me to do and be better.” A defining feature of the UChicago Charter School is a college-going environment of high academic achievement that highlights issues of race, class and gender. While the Woodlawn campus is steeped in messages and visuals encouraging students to think college, for the Singleton sisters, the full-court college press wasn’t necessary. College was always the goal. “My parents are great people, but from an early age, I felt that I didn’t want to struggle the way that they did,” Olivia says. “I always thought that college was the way to avoid that.”

Their College Search Ended with a Big Surprise

Number one and two in their graduating class, Aliyah and Olivia had a lot of options. “I was sure I was going far, far away for college,” laughs Olivia. A UChicago Charter School board member financed a trip for the twins to visit schools in New Jersey and Pennsylvania. It was the first time they had ever been on a plane. Aliyah fell hard for Princeton University, while Olivia set her sights on Lafayette College. Fueled by her mother’s prediction, Aliyah also applied to the University of Chicago, while Olivia wasn’t convinced she had a chance. It wasn’t until the final hour that Olivia also submitted an application. Ultimately, both were looking for the school that would give them the best financial packages. Debt was not an option. In February 2014, it was a seemingly normal day in the halls of UCW when the Singleton sisters were called into the school gymnasium. Upon walking through the double doors, they saw their entire family—crying. Music started playing. Amidst the confusion, someone said that Aliyah had been accepted to the University of Chicago. Olivia remembers being thrilled for her sister when she heard her mother say, “and so has Olivia!” Both had not only been accepted into the University of Chicago, they had also received full scholarships. “I had wanted to go to Lafayette because I never imagined I would get into UChicago. When it happened, it was a no-brainer to fulfill my mom’s hope for us,” says Olivia.

As College Grads, They’re Giving Back

This past June, both sisters graduated from the University of Chicago—the future their mother had always envisioned for them. Olivia got her degree in political science while Aliyah studied comparative human development. Even so, college was not always smooth sailing. “Going to college was a huge culture shock,” says Aliyah. “At times, because of my skin color and background, I didn’t feel like I was good enough. My education at UCW helped me stay strong and feel confident in who I am through my college experience.” Over the summer, Olivia and Aliyah interned at the Academy Group, an educational social enterprise that provides academic support, mentoring and work experience for young people of color in Chicago. The group is co-founded by Shayne Evans, former director of the University of Chicago Charter School. Now, it looks like both may start careers there. Olivia has accepted a role as a learning designer. She provides direct instructional and advising support to young people during the Academy Group’s Summer Academy, and during after-school and weekend programming. She also designs and executes innovative education programming, helps develop staff and coaches tutors. She plans to eventually go to business school. Aliyah says she will apply to law school in a couple of years but has an interview with the Academy Group for a project manager role. Regardless of their destination, both women see their futures giving back to underserved communities and hopefully, helping more students like themselves graduate from the University of Chicago and beyond.
Katelyn Silva
Katelyn Silva is mom to a third grader and an education writer in Providence, Rhode Island. She operates her own education writing consulting business. She was previously the chief communications officer at Rhode Island Mayoral Academies, a nonprofit dedicated to opening intentionally diverse public charter schools. Prior to that, she was the communications director at the University of Chicago ...

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