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.
01:10:31
forum Ask episode
web_stories AI Snips
view_agenda Chapters
menu_book Books
auto_awesome Transcript
info_circle Episode notes
question_answer ANECDOTE
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.
insights INSIGHT
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.
volunteer_activism ADVICE
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.
Get the Snipd Podcast app to discover more snips from this episode
Call Sign Chaos is a memoir that chronicles General Jim Mattis's career from his early days as a Marine recruit to his role as a four-star general and Secretary of Defense. The book is divided into three parts: Direct Leadership, Executive Leadership, and Strategic Leadership. Mattis recounts his foundational experiences, extracting lessons on warfighting, peacemaking, the importance of allies, and strategic dilemmas. He emphasizes the need for America to return to a strategic footing to avoid fighting inconclusive wars. The book offers a unique leadership philosophy developed through constant study and action, making it relevant for both military and civilian leaders.
The Daily Stoic
366 Meditations on Wisdom, Perseverance, and the Art of Living
Ryan Holiday
Stephen Hanselman
This book provides 366 meditations on Stoic wisdom, featuring new translations of passages from Epictetus, Marcus Aurelius, Seneca, and other Stoic philosophers. Each day, readers are presented with a Stoic lesson explained in modern language, along with advice on how to apply these lessons in everyday life. The book is organized temporally and thematically across the twelve months of the year, making it a daily resource for practicing Stoicism[4][5][6].
The Afghanistan Papers
Craig Whitlock
The Washington Post
The Afghanistan Papers is a non-fiction book that exposes the U.S. government's decades-long failures in Afghanistan. Based on leaked documents and interviews, the book reveals a pattern of deception and misrepresentation regarding the war's progress and objectives. The authors detail how U.S. officials consistently downplayed the challenges and overstated their successes, leading to a prolonged and ultimately unsuccessful military campaign. The book raises serious questions about government transparency and accountability, and its impact on public trust. The Afghanistan Papers provides a critical examination of the war's history and its lasting consequences.
The Unbearable Lightness of Being
Milan Kundera
Set in Czechoslovakia during the 1968 Prague Spring and its aftermath, 'The Unbearable Lightness of Being' follows the lives of Tomáš, a surgeon and serial adulterer; Tereza, his wife; Sabina, Tomáš's mistress and an artist; and Franz, Sabina's lover. The novel delves into philosophical themes such as the concept of 'lightness' versus 'heaviness', drawing from the ideas of Nietzsche and Parmenides. It explores the characters' experiences with love, sex, loyalty, and betrayal, all set against the political turmoil of the time. The story examines the human condition, the search for meaning and happiness, and the consequences of the choices made by the characters[2][3][5].
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.
The Daily Stoic 
