Ep 147- On Character with General Stanley McChrystal

May 23, 2025

In this powerful conversation, retired four-star General Stanley McChrystal joins Joe to discuss his new book, On Character: Choices That Define a Life. Drawing from decades of military leadership and personal reflection, General McChrystal breaks down why character is more than just a word—it’s a daily practice rooted in conviction and discipline.

In this episode, they explore:

  • Why journaling would have made him a better leader
  • A practical method he used to align his time with his priorities in Afghanistan
  • How reading shaped his thinking both in and out of uniform
  • The subtle but dangerous effects of power on rising leaders
  • Why leaders must continuously test their convictions under pressure

Whether you’re in uniform or leading in another capacity, this episode is a must-listen for anyone striving to lead with authenticity, courage, and character.

Meet General McChrystal

Stan McChrystal retired in July 2010 as a four-star general after over 34 years of service in the U.S. Army. His final assignment was as the commander of NATO’s International Security Assistance Force and all US forces in Afghanistan. He had previously served as the director of the Joint Staff and almost five years in command of the Joint Special Operations Command.

General McChrystal’s memoir, My Share of the Task, was a New York Times bestseller in 2013. He is also the author of New York Times bestseller Team of Teams: New Rules of Engagement for a Complex World and wrote the forward for the sequel, One Mission:How Leaders Build a Team of Teams. He is a senior fellow at Yale University’s Jackson Institute for Global Affairs and a partner at McChrystal Group, where he transforms organizations into adaptable teams. He and his wife, Annie, live in Virginia.

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