“Dare to Be True” Is a Lesson for Life, Grammy-Nominated Musician Jidenna Tells Students

Rapper and singer Jidenna Mobisson ’03 returned to campus as part of the expanded Transition Program (see page 32), serving as the keynote speaker for new students of color and international students, and as a panelist in a conversation with their parents. The events preceded programming throughout Labor Day weekend for all students new to Milton.

“It’s the first day — I know you feel a little bit nervous, but I want to say congratulations to each and every one of you,” Jidenna said. “I sat in the same seats you’re sitting in right now, with students who were just like you. Some of the people here that you don’t know yet will be your best friends for life.”

Born in Wisconsin, Jidenna moved to Nigeria with his family and lived there until the age of six. Upon returning to the United States, the family settled in Massachusetts. Throughout his youth, he encountered racism from children and adults that made him question his sense of belonging in certain places. His family lived in the working-class Boston neighborhood of Mattapan, which borders Milton but felt like a world away from campus. Jidenna recalled feeling embarrassed by his mom’s car, asking her to drop him off at the edge of campus on the days he didn’t walk from the train station.

Jidenna offered tips for rising to the challenges of a rigorous environment like Milton. First, he advised students to work closely with the faculty, because teachers are invested in student success — he remains in touch with teachers who have become friends over the years. He also advised students to embrace the diversity of the School and to get to know students with identities and backgrounds different from their own. As well as sharing their lives with faculty and peers, he said, students should follow the School’s motto.

“I’ve never forgotten ‘Dare to be true,’” Jidenna said. “It takes courage to find your vulnerabilities. It takes courage to embrace them. But when you do, you become a mighty person, and you’re able to walk on your own.”

Students should expect to grow in their understanding of identity during their time at Milton, Jidenna said. Through his African American history course, he learned about leaders who helped shape his understanding of what it means to be black; through his peers with different identities, he learned the importance of finding — and using — one’s own voice.

After graduating from Milton, Jidenna attended Stanford, where he studied ritual arts. He is signed to Janelle Monáe’s Wondaland Records, and his song “Classic Man” received a Grammy Award nomination in 2016. In the summer of 2019, he released the album 85 to Africa, which showcases his influences of African and Caribbean music, hip-hop, and soul.


The curiosity to ask why and the courage to speak out are qualities that lead to innovation and change. The individuals featured in this issue embody these qualities. Through their questioning, leadership, and willingness to share their views, they are making a difference–in their professions and in the world.