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

0:00Ryan Holiday: Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

0:14Ryan Holiday: I wanted to start with 9-11. You know, 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? Of course. On September 11, 2001, I was actually stationed here in Washington, D.C., 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.

0:59And, you know, we had just gotten back as a squadron from out in Las Vegas and 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. And I was not scheduled to fly that day. I was originally sort of running the flying operation for the squadron as the chief instructor and tactician. You know, as we came in that morning, we obviously had no idea what we were going to face. And we were in a meeting at the squadron, just a training meeting, when one of our young intelligence professionals came in and said, an airplane has just hit the World Trade Center.

1:45And of course, my first thought was, it's a small civilian airplane. This couldn't be. And as you get older, as leaders, you start to develop that spidey sense of just something's not right. And I felt that, got up, walked into our squadron lounge where we had a big flat screen TV. And remember, I still get chills today even, remember clearly the helicopter news shot showing the first tower burning when the second airplane flew into the picture and hit the building. silence could have heard a pin drop and we sat there for what seemed like a long time which was probably just a very few seconds and 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.

2:58The 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, make sure this is for you. And we went and got ready to fly. 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 met Gerald Worley. Gerald 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 the call and on the video here, I will never forget what then General Worley said to us.

3:53He's just read us the rules of engagement, which are extremely liberal. The decision is clearly mine as the top commander, the mission commander over the combat air control. And he reads us verbatim. 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.

4:33We ran to the jets and scrambled 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 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 the rest of that day, a lot of intercepts, and a lot of sort of keeping airplanes away from downtown Washington.

5:20And our squadron flew for the next 45 days after that. I deployed pretty quickly overseas to start fighting al-Qaeda.

5:30Ryan Holiday: Well, to bring all that together, I think there's a couple 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 book about Admiral Rickover recently. They just sort of mentioned it offhandedly. But I guess for maybe it's still the case, but it was the case during the Cold War, that every commander of a nuclear submarine could directly call the White House. Like there was just a phone they could pick up and it would ring at the president's desk. And so I think sometimes we think these these organizations are huge and there's this massive chain of command.

6:11Ryan Holiday: But at the top, it sounds like. Well, we didn't call they called us just to be clear. You know, I called the Secret Service. But that's what I mean. That's what I mean. Yeah. Is that at the at the end of the day, the really elite operators have to be completely flat. There has to be open lines of communication and flexibility there. 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 lead, serve, and help with, then we can't possibly understand what's really going on.

7:00So flatness is the key to that.

7:02Ryan Holiday: Yeah, because often, you know, I think, especially at the lower levels, you can be like, well, I pass this up the chain and something will happen. But 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 use 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? 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.

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10:00Ryan 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, a handful of people talking on 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 I thought it was remarkable is that you had this 911 operator relaying information from all over the world, sort of that all these people involved, although they had no official authority or even official obligation to do anything, took it upon themselves to say, look, we might not be able to solve this thing, but we cannot contribute to the problem.

10:56Ryan Holiday: We cannot make this tragic event more tragic, and we're going to try to do something. And 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 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 out of this tragedy of September 11th, we can find incredible goodness on who we really are as a country.

11:48And I hope we just always take advantage of those examples moving forward.

11:54Ryan Holiday: Yeah, you know, it's almost easy to celebrate the firefighters and the police officers, but there were also the office managers and the employees and the people who had, you know, they work in this enormous office together, but they never met before. 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 is. Leadership isn't this thing you get promoted to necessarily. It's also what you do in moments of crisis. Absolutely. Absolutely. It could have been a lot worse that day at those people not evacuated the towers and those people stood in the stairwells, helped other people get down there.

12:39People in the Pentagon could have been a lot worse.

12:41Ryan Holiday: Or that plane, you know, Flight 93 could have crashed into the White House or Capitol building. Would have been much worse. And then when I think about leadership, although thankfully you didn't have to, it strikes me that what your commander was talking about was the idea that within the latitude that you had been given, you potentially would have to make some very hard decisions in the moment, which is also 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? Yeah, you know, and as I reflected on that day, and look, we just did our jobs.

13:23We just did our jobs. And thankfully, we didn't have to make the decision to shoot somebody down. So as I reflected back on that day and folks have asked me, you know, were you scared or what was going through your mind and whatnot? Of course, but overwhelmingly, the thing that I'm grateful for this experience in some ways as a leader, my largest concern was not to miss somebody and not to be able to prevent or be unable to prevent an airplane going into the White House, going into the Capitol. And that drove everything. And as I didn't realize it at the time, I was younger and a young captain.

14:09But as I've reflected on that over the years, I'm grateful for that and other situations like that, where 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. information in short amounts of time. And that is something that I've learned that value created.