Meet Caleb
STUDENTS | June 15, 2020
Meet Caleb

A Whitney Young Graduate Eager to Use Entrepreneurship to Prompt Structural Changes in Society


When Caleb Dunson was admitted to Whitney Young High School’s Academic Center for seventh grade, it wasn’t long before people from across the country knew about his acceptance. He was featured in SelectED, a documentary that highlighted Whitney Young as one of the top schools in the country. While he entered the school knowing little beyond that Jahlil Okafor was an alum, he leaves Whitney Young grateful for the countless opportunities he has been given. 

“At Whitney Young, I had the opportunity to study abroad in South Africa this past summer because of one of my language teachers. I spent six weeks taking a college course at the University of Michigan because of the former dean of students,” he said. “My high school experience has been an abundance of opportunities and a community of people who are willing to push you to do your best.” 

Even before attending Young, Caleb’s time as a CPS student was marked by passionate teachers who always pushed him to go above and beyond what he thought he was capable of. He’ll never forget his kindergarten teacher at Skinner West Elementary School who treated him and his classmates as if they were adults, having them give presentations as five-year-olds and memorize all the U.S. states in alphabetical order. In high school, he formed a special connection with Ms. Lent, his AP U.S. Government and Politics teacher, who has been his advisor on a senior independent research project, which centers on him organizing a series of panel discussions about identity and being part of a national civics fellowship. 

“Since kindergarten, my teachers have planted and fostered seeds of curiosity in me that have grown and allowed me to be successful,” he said. 

Though he’s loved his classes, many of Caleb’s favorite high school memories have taken place outside of the classroom. He’ll never forget his first Taste of Whitney Young, the school’s version of the annual Taste of Chicago food festival. One day, he and some of his friends spontaneously went to the Google headquarters a few miles away from Young to try to get a tour. They were unsuccessful, but they had an enlightening conversation about the beauty of coding and computer science with a Google employee. Caleb is now a potential computer science major thanks in part to that conversation. Whether studying together, participating in a summer program, or exploring the city, Caleb notes that he will miss the tight-knit connections he shares with other Chicago youth. 

“With all the programs like After School Matters and One Summer Chicago, the youth world in Chicago ends up feeling very small,” he said. “You start to meet people who are friends with other people that you know, and it feels like a small community of people who are trying to lift each other up and cheer each other on.” 

While Caleb is quick to say that he jumps from interest to interest, they tend to converge at the intersection of business, entrepreneurship, and social justice. He even started his own non-profit, the Youth Entrepreneurship League, to help young entrepreneurs start and grow their own businesses. He’s leaving Chicago for the time being to attend Yale University, but there’s no question that he might be back soon ready to use his gifts to maximize his social impact. 

“Find something you love to do and learn how to do it exceptionally well,” he said. “Everybody has a special talent, and all it takes is a little bit of digging to find that out. Once you find your passion, use it to help others.”