Mistakes vs. Stupidity: Leadership and Life Lessons with C.J. Stewart

My guest for Episode #308 of the My Favorite Mistake podcast is C.J. Stewart, co-founder and Chief Visionary Officer at the LEAD Center for Youth, an Atlanta-based nonprofit focused on empowering Black youth through sports-based development. Before dedicating his life to mentorship and advocacy, C.J. was drafted twice by the Chicago Cubs and built a successful career as a professional hitting instructor and co-owner of Diamond Directors. He’s also the author of Living to Lead: A Story of Passion, Purpose, and Grit.

Episode page with video and more

C.J.’s “favorite mistake”? Becoming an avid runner. What started as a tribute to the life of Ahmaud Arbery turned into a transformational habit—one that reshaped his health, mindset, and mission. In this powerful conversation, C.J. unpacks the difference between mistakes and stupidity, explores the struggles that shape significance, and reflects on the emotional toll and systemic barriers faced by Black athletes. He also shares how running has helped him connect across generations, communities, and cultures.

Throughout the episode, C.J. offers a candid and thought-provoking look at racism, leadership, and the need for real advocacy—not just good coaching. He shares insights from his own life as a player, coach, and nonprofit leader, challenging listeners to consider how we name and respond to problems, and why protecting others is at the heart of leadership. This is a conversation about growth, conviction, and using our platforms to make a difference.

Questions and Topics:

• What’s your favorite mistake, and what did you learn from it?
• In what way was becoming a runner a mistake?
• How do you define the difference between a mistake and stupidity?
• How has running changed you—physically, emotionally, and socially?
• Did pursuing a career in professional baseball feel like a mistake in hindsight?
• What does LEAD stand for, and what is its mission?
• Why is advocacy more important than just good coaching?
• Why do you think there are so few Black players in certain positions, like catcher or pitcher?
• What needs to change in baseball to address racism and systemic barriers?
• What do you mean when you say you became “openly Black” in 2015?
• How does racism take an emotional toll on Black athletes, even those who succeed?
• Are MLB diversity programs effective, or are they falling short?
• What else needs to happen to create real change and equity in baseball?