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123: General Stan McChrystal — How to Face Fear, Pivot from Failure, and Live a Disciplined Life

May 15, 2025 by Cal Walters

The views expressed on this podcast and page are those of the host and guests and do not necessarily reflect the official policy, position, or endorsement of the US Army, DoD, or the US Government.

In this conversation, General Stanley McChrystal discusses the profound impact of character on leadership, emphasizing that true leadership is tested during challenging times. He reflects on his personal experiences, including his resignation from the military, and how his marriage has shaped his character. The discussion also delves into the importance of understanding core values, the influence of parents on our convictions, and the role of fear in leadership decisions. McChrystal encourages leaders to clarify their values and to recognize that character is a choice that defines us.

In this conversation, Stanley McChrystal discusses the dynamics of leadership, the importance of courage in speaking up against groupthink, and the necessity of discipline in personal and professional life. He reflects on his experiences in high-pressure environments, the challenges of maintaining integrity, and the value of writing as a tool for clarifying thoughts and fostering a national dialogue on character. The discussion emphasizes the significance of learning from mistakes and the impact of personal values on leadership effectiveness.

Stan McChrystal founded McChrystal Group in January 2011 to deliver innovative leadership solutions to businesses globally in order to help them transform and succeed in challenging, dynamic environments. As Founder and a Partner, he advises senior executives at multinational corporations on navigating complex change and building stronger teams.

A retired four-star general, Stan is the former commander of US and International Security Assistance Forces (ISAF) Afghanistan and the former commander of the nation’s premier military counter-terrorism force, Joint Special Operations Command (JSOC). He is best known for developing and implementing a comprehensive counterinsurgency strategy in Afghanistan, and for creating a cohesive counter-terrorism organization that revolutionized the interagency operating culture.

Throughout his military career, Stan commanded a number of elite organizations, including the 75th Ranger Regiment. After 9/11 until his retirement in 2010, he spent more than 6 years deployed to combat in a variety of leadership positions. In June 2009, the President of the United States and the Secretary General of NATO appointed him to be the Commander of US Forces Afghanistan and NATO ISAF. His command included more than 150,000 troops from 45 allied countries. On August 1, 2010 he retired from the US Army.

In 2013, Stan published his memoir, My Share of the Task, which was a New York Times bestseller; and is an author of Team of Teams: New Rules of Engagement for a Complex World, which was a New York Times bestseller in 2015. Stan also co-authored Leaders: Myth and Reality, a Wall Street Journal Bestseller based on the epochal Parallel Lives by Plutarch. He previously served as a senior fellow at Yale University’s Jackson Institute for Global Affairs, where he also taught a course on Leadership. He currently sits on the boards of Navistar International Corporation, Siemens Government Technology, and JetBlue Airways. He is a sought-after speaker, giving speeches on leadership and team dynamics to organizations around the country.

A passionate advocate for national service and veterans’ issues, Stan is the Chair of the Board of Service Year Alliance. In this capacity, he advocates for a future in which a year of full-time service—a service year—is a common expectation and opportunity for all young Americans.

Stan is a graduate of the United States Military Academy at West Point and the Naval War College. He also completed year-long fellowships at Harvard’s John F. Kennedy School of Government and the Council on Foreign Relations.

On Character: Choices That Define a Life
By McChrystal, General Stanley

If you’re interested in discovering your core values and becoming a more self-aware and emotionally intelligent leader, I’ve built the perfect course to help you get there. Check out my Discover Your Core Values Mini Course, where I coach you through 3 exercises of guided reflection and help you uncover your core values in a way that you can apply them right away.

May 15, 2025 /Cal Walters
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