The Daily Stoic26 Apr 2025

Leadership Lessons from Gen. Dan Caine | 9/11 Pilot to Chairman of the Joint Chiefs of Staff

Just after 2 a.m. on April 11, the U.S. Senate confirmed retired Air Force Lieutenant General Dan Caine as the 22nd Chairman of the Joint Chiefs of Staff. As it turns out, Ryan had the opportunity to interview Gen. Caine a few years ago as part of The Daily Stoic Leadership Challenge.

In honor of his recent confirmation, today’s episode is Ryan and Gen. Caine's powerful conversation. Gen. Caine reflects on being one of the first pilots in the air on 9/11, the core traits every great leader must embody, and how to effectively inspire and guide a team toward a shared mission.

General Dan Caine is the 22nd Chairman of the Joint Chiefs of Staff. He has flown more than 100 combat hours in F-16 aircraft. His total flight hours are 2,800. Throughout his career he was awarded the Defense Superior Service Medal, Distinguished Flying Cross, Bronze Star Medal with bronze oak leaf cluster and the Defense Meritorious Service Medal.

💡 Want more insights from extraordinary leaders like General Caine? Check out The Daily Stoic Leadership Challenge at store.dailystoic.com.

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