What a 9/11 Pilot Will Never Forget | General Dan Caine (BONUS)

In today’s bonus episode, Gen. Dan Caine reflects on being one of the first pilots in the air on 9/11 and what that moment taught him about courage, leadership, and service. 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 https://store.dailystoic.com/products/copy-of-the-daily-stoic-leadership-challenge-ancient-wisdom-for-modern-leaders at store.dailystoic.com https://store.dailystoic.com/products/copy-of-the-daily-stoic-leadership-challenge-ancient-wisdom-for-modern-leaders. 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/ 📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work":https://store.dailystoic.com/pages/wisdom-takes-work 🎙️ Follow The Daily Stoic Podcast on Instagram https://www.instagram.com/dailystoicpodcast/?hl=en: https://www.instagram.com/dailystoicpodcast 🎥 Watch top moments from The Daily Stoic Podcast https://www.youtube.com/@dailystoicpodcast on YouTube https://www.youtube.com/@dailystoicpodcast: https://www.youtube.com/@dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail 🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/ 📱 Follow us: Instagram https://www.instagram.com/dailystoic/,Twitter https://twitter.com/dailystoic,YouTube https://www.youtube.com/@DailyStoic,TikTok https://www.tiktok.com/@daily_stoic?lang=en, andFacebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:05Speaker 00

  Welcome to the Daily Stoic Podcast, where each day we bring you a Stoic-inspired meditation, designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of history's greatest men and women, help you learn from them, to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visit DailyStoic.com.

• 0:56Ryan Holiday?

  I wanted to start with 9/11. We've talked to a bunch of interesting leaders, and they've been through some crises and difficulties, but nothing quite like being one of the first planes in the sky on 9/11. So could you maybe walk us through that day and what that was like?

• 1:14Speaker 02

  Of course. On September 11, 2001, I was actually stationed here in Washington DC out at Andrews Air Force Base. I was flying F-16s. I'd been to the Air Force's Top Gun School, where we don't play much volleyball. We mostly focus on getting better as tacticians with a little bit of jest towards my Navy brothers and sisters. And we had just gotten back as a squadron from out in Las Vegas at Nellis Air Force Base, where we were getting ready to deploy. And you know, that Tuesday here in Washington was a beautiful and gorgeous day.

• 1:57Speaker 02

  And I was not scheduled to fly that day. I was originally sort of running the flying operation for, for the squadron as the chief instructor and tactician, you know, as we came in that morning, we obviously had, had no idea what we were gonna face. And we were in a meeting at the squadron, just a, a training meeting, when one of our young intelligence professionals came in and said, "An airplane has, has just hit the World Trade Center." And of course, my first thought was, "It's a small civilian airplane, this couldn't be."

• 2:35Speaker 02

  And as you get older, as leaders, you start to develop that spidey sense of just something's not right. And I, I felt that, got up, walked into our, our squadron lounge, where we had a, a big flatscreen TV. And, and remember, I still get chills today even, remember clearly, the helicopter news shot showing the first tower burning, when, when the second airplane flew into the picture and, and hit, hit the building. Silence. Could've heard a pin drop and we sat there for what seemed like

• 3:18Speaker 02

  a long time, which was probably just a very few seconds. And I, I went to the, to the desk where we had all of our communications gear. And I picked up the phone and called the Secret Service and said, "I don't know what's going on, what do you need us to do?" We had a relationship with the Secret Service in Washington because we flew out of the same airfield as the president. The next phone call was the White House, saying, "Get anything you can airborne. The nation is under attack." And right at that point in time, My boss Brigadier General Dave Worley walked in and I handed him the phone. And I said, hey sir, this is, this is for you. And we went and got ready to fly.

• 4:02Speaker 02

  And it was myself and a wingman and there were two other folks as well. And we got our gear on and went running back to the ops desk and, and, and met General Worley. General Worley read us the rules of engagement for defending the National Command Authority. It was very liberal and it was on us. And, you know, when you think about leadership for the folks on, on the, on the call and on the video here. I will never forget what then General Worley said to us. He's just read us the rules of engagement, which are extremely liberal. The decision is clearly mine. It's the cap commander, the mission commander over the Combat Air Patrol. And he reads us verbatim.

• 4:47Speaker 02

  And then he pauses and he looks at us and says, hey Dan, look. I don't know what you're going to face out there. I think you're probably going to have to make some very difficult decisions, but here's what I want you to know. I trust you. You're going to do the right thing. And no matter what, I have your back. And you want to talk about saying the exact, exact right thing at the exact right moment. Uh, we ran to the jets and scrambled and, and, you know, we're flying that morning. We took off, I think, right around the same time that the real heroes or some of the real heroes of that day, the passengers of Flight 93 were, were assaulting inside the airplane.

• 5:33Speaker 02

  Knowing full well what they were facing, knowing what had happened in New York City. And yet finding the courage to step up, not having taken the same oath that we take to uphold and defend the Constitution, but knowing that their nation needed them to do something. So flew that, the rest of that day and. A lot of intercepts and a lot of sort of keeping, keeping airplanes away from downtown Washington and our squadron flew for the next forty-five days after that and I deployed pretty quickly overseas to, uh, to start fighting Al Qaeda.

• 6:11Ryan Holiday?

  Well, to bring all that together, I, I think there's a couple of interesting themes. So one, which is open lines of communication. I think it's pretty incredible that you're just sort of very quickly on the phone with the White House. I was reading a, a book about Admiral Rickover recently. They, they just sort of mentioned it offhandedly, but I guess for, maybe it's still the case or, but it was the case in the, during the Cold War, that every, uh, commander of a nuclear submarine could directly call the White House. Like there was just a phone they could pick up and the, it would ring at the president's desk. And, and so I think sometimes we think these, these organizations are huge and there's this massive chain of command, but at the top, it sounds like, uh-

• 6:55Speaker 02

  Well, we didn't call, they called us, um, just to be clear. You know, I called the Secret Service.

• 7:01Ryan Holiday?

  But that's what I mean. That's what I mean.

• 7:03Speaker 02

  Yeah.

• 7:03Ryan Holiday?

  Is, is that at the, at the end of the day, at the really elite operators-

• 7:07Speaker 02

  Yeah.

• 7:07Ryan Holiday?

  Have to be completely flat. There has to be open lines of communication and flexibility there.

• 7:13Speaker 02

  And flatness is something from a leadership perspective that we value greatly. Certainly I value greatly and I drive the organizations that I'm blessed to lead or be a part of towards that flatness. I think as leaders, if we don't understand what is happening at the edge of the empires that we're blessed to, to lead, serve and, and, and help with, then, then we can't possibly understand what's, what's really going on. So flatness is a key to that.

• 7:43Ryan Holiday?

  Yeah. Because often, you know, I think especially at the, the, the lower levels, you can be like, well, I, I pass this up the chain and something will happen. But I, I, I think it's interesting that, yeah, you called the Secret Service. You didn't sort of wait around and say, let's see if somebody needs me. Let's wait to see where this goes. You sort of used the contacts you had on that day to sort of say, you know, what do you need from me? What can I contribute? What's going on?

• 8:09Speaker 02

  I think we've got a responsibility as leaders, at whatever level you're leading at, to be proactive and not reactive, to realize when there's a white space and lead your organization or yourself towards that white space to improve the overall effectiveness, efficiency, combat, whatever kind of organization you're leading and move towards the problem.

• 8:47Ryan Holiday?

  When that goes to the passengers on Flight 93, which you texted me a transcript of that call on 9/11, which I was, it always sort of gives you the chills to read. I think the idea that, yeah, they weren't sort of technically leaders in any way. It was, you know, a handful of people talking on, you know, phones on airplanes, which I think younger people don't even remember was a thing, that you could swipe your card and get a handset out of the back of a seat. But they sort of anointed themselves leaders. And it was, I thought was remarkable is that you had this 911 operator relaying information from all over the world. It sort of, that all these people involved, although they had no official authority

• 9:31Ryan Holiday?

  or even official obligation to do anything, took it upon themselves to say like, "Look, we might not be able to solve this thing, but we can not contribute to the problem. We can not make this tragic event more tragic, and we're going to try to do something."

• 9:49Speaker 02

  And I, you know, I just, I think about them every day, right? And that is real courage, knowing what is going on in the United States at that point in time. And... Having the intestinal fortitude, the bravery to stand up and go forward, knowing, uh, it's just an incredible example. You know, America started to fight back immediately. And they were the first steps, the firefighters that headed up buildings were the first steps. You know, the people at the Pentagon were the first steps. And, and out of this tragedy of September 11th, we can find incredible goodness

• 10:32Speaker 02

  on who we really are as a country. And I hope we just always take advantage of those, those examples moving forward.

• 10:41Ryan Holiday?

  Yeah, you know, it's, it's almost easy to celebrate the firefighters and the police officers, but, but there were also the office managers and the employees and the, the people who had, you know, they worked in this enormous office together, but had never met before. And, and again, had no real obligation to anyone but themselves and decided, hey, I'm not leaving anyone behind, or hey, I'm going to do what I can here. That is also what leadership, leadership isn't this thing you get promoted to necessarily. It's also what you do in moments of crisis.

• 11:13Speaker 02

  Absolutely, absolutely. It could have been a lot worse that day, had those people not evacuated the towers and, and those people stood in the, in the stairwells, helped other people get down there, or people in the Pentagon. It could have been a lot worse.

• 11:27Ryan Holiday?

  Or that plane, you know, flight 93 could have crashed into the White House or the Capitol building.

• 11:32Speaker 02

  Would have been much worse.

• 11:34Ryan Holiday?

  And, and then when I think about leadership, although thankfully you didn't have to, um, it strikes me that what your commander was talking about was the idea that within the latitude that you had been given, you would have, you potentially would have to make some very hard decisions in the moment, which is also, you know, something we've talked about. But sort of the definition of leadership to me is, you know, can you make hard decisions with limited information and limited time?

• 12:04Speaker 02

  Yeah, you know, and as, as I reflected on that day, and look, we just did our jobs. We just did our jobs and thankfully we didn't have to make the decision to shoot somebody down. As I reflected back on that day and folks have asked me, you know, were you scared? Or what, or what was going through your mind and whatnot? Of course, but overwhelmingly, the thing that, and I'm grateful for this experience in some ways as a leader. My largest concern was not to miss somebody and not to, and not to be able to prevent, be unable to prevent an airplane going into the White House, going into the Capitol.

• 12:47Speaker 02

  And, and that drove everything. And as, I didn't realize it at the time, I was younger and a captain, you know, a young captain. But as I've reflected on that over the years, I'm grateful for that and other situations like that, where I, I built some trust and confidence in my own instincts as a leader to be able to make difficult and complex decisions with limited information in short amounts of time. And, and that is something that, that I've, I've learned to value greatly.

• 13:28Ryan Holiday?

  Hey, it's Ryan. Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please spread the word, tell people about it. And this isn't to sell anything, I just wanted to say thank you.