Raekwon Bolling

Age 20, Class of 2019

Legacy Youth Participant 


Raekwon was raised on the south side of Chicago and attended Harlan Community Academy High School, earning his high school diploma. He participated in the Legacy Youth after-school program during his time as a high school student and spent the summer after his sophomore year of college working as a Legacy Leaders intern. Throughout his time as a Legacy Youth participant, he traveled with the program to Lake Geneva, WI for a leadership retreat.

Currently Attending: Alcorn State University, Third Year Student

Major(s): Accounting and Business Administration

Extracurricular Activities: Member of the National Society of Pershing Rifles Fraternity.  

Favorite Legacy Youth Lesson: My three favorite lessons were Toxic Thinking, Servant Leadership, and Becoming a Great Follower. I learned that being a leader involved positivity and humility. Leadership is not about giving orders; it is about setting goals and working as a team to achieve them. These lessons have been beneficial as I navigate relationships on campus and in life.

Proudest Accomplishment to Date: The decision to attend college out of state has been my proudest accomplishment to date. The transition was difficult, especially as I dealt with homesickness during the first few months of my first year. However, one thing I took away from my experience with Legacy Leaders is the power of positivity. I made an effort to get connected on campus and did my best to remain positive about my situation. Being away from home hasn’t always been easy, but it has been a worthwhile experience.

Future Goals: I am working hard to complete my degree, which is my immediate goal. In the coming years, I would like to find a way to give back to high school students who share a similar background with me. I want to encourage them to consider opportunities outside of their comfort zone, like going away for college or studying abroad. It is important to set the example and show others that opportunities are everywhere; you just have to pursue them.

Advice for Current Legacy Youth: Staying in your comfort zone will only hinder you, challenge yourself to pursue what scares you.

“Legacy Leaders gave me the skills to effectively communicate with people and the tools to apply critical thinking during difficult situations.”

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