The Daily Stoic Leadership Lessons from Gen. Dan Caine | 9/11 Pilot to Chairman of the Joint Chiefs of Staff
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Apr 26, 2025 
Dan Caine, a retired Air Force Lieutenant General and the 22nd Chairman of the Joint Chiefs of Staff, shares gripping insights from his career. He discusses his experience as one of the first pilots on 9/11 and the essential traits of effective leaders. Caine emphasizes adaptability, continuous learning, and open communication in leadership roles. He highlights how ordinary individuals can display extraordinary courage in crises and the importance of cultivating morning routines for personal growth and productivity.
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General Caine's 9-11 Combat Experience
- On 9-11, Dan Caine and his squadron scrambled F-16s to defend Washington, D.C. against incoming threats.
- They acted decisively with trust from leadership and flew for 45 days after, engaging in intercepts to protect the capital.
Flat Communication in Leadership
- Elite military operators rely on open, flat communication rather than rigid chains of command.
- Leaders must proactively engage and move toward problems rather than waiting passively.
Humble Problem Definition for Leaders
- Leaders should be humble and admit mistakes while continuously learning and improving.
- Define the problem clearly with your team to ensure everyone understands the challenge before acting.
