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

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. 🎟️ DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️ AD-FREE https://dailystoic.supercast.com/| 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/ https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail -- Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. -- Wealthfront’s high-yield cash account: https://www.wealthfront.com/stoic This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details at wealthfront.com/promo-terms. The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of January 30, 2026, is representative, requires no minimum, and may change at any time. References to the APY for the Wealthfront Cash Account, including any APY increase, are to the APY paid by insured depository institutions that participate in our cash sweep program (the "Program Banks”). Wealthfront Brokerage does not pay interest. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Instant and same-day withdrawals use the Real-Time Payments (RTP) network or FedNow service. Transfers may be limited by your receiving institution, daily caps, or participating entities. New Cash Account deposits have a 2–4 day hold before transfer. Wealthfront does not charge fees for these services, but receiving institutions may impose an RTP or FedNow Fee. Processing times may vary.. Fees & Eligibility requirements may apply to certain checking features. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Investing involves risk, including the possible loss of principal. Securities investments are not bank deposits, bank-guaranteed or FDIC-insured, and may lose value. 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.

• 0:00Ryan 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.

• 0:15Ryan Holiday?

  I wanted to start with 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?

• 0:33Speaker 01

  Of course, on September 11th, 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 on getting better as tacticians with a little bit of jest towards my Navy brothers and sisters. And, you know, 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.

• 1:16Speaker 01

  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 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 has just hit the World Trade Center." And 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.

• 2:01Speaker 01

  And I felt that, got up, walked into our squadron lounge, where we had 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 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.

• 2:46Speaker 01

  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, "Make sure that this is 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.

• 3:27Speaker 01

  And we got our gear on and went running back to the Ops desk and 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 on the call and on the video here, I will never forget what then Gerald 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 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.

• 4:12Speaker 01

  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. We 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,

• 4:52Speaker 01

  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 yearned 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 45 days after that. And I deployed pretty quickly overseas to 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, or 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 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.

• 6:14Speaker 01

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

• 6:19Ryan Holiday?

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

• 6:21Speaker 01

  Yeah.

• 6:22Ryan Holiday?

  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.

• 6:32Speaker 01

  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 to help with, then then we can't possibly understand what's what's really going on. So flatness is a key to that.

• 7:02Ryan Holiday?

  Yeah, because often, you know, I think especially at the the lower levels, you can be like, "Well, I 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 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?"

• 7:28Speaker 01

  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 and move towards the problem.

• 8:05Ryan Holiday?

  When that goes to the passengers on Flight 93, which you you texted me a transcript of of that call on 9/11, which I was, it's, 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 of a seat. But they they sort of anointed themselves leaders. And it was, I thought it 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

• 8:49Ryan 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 cannot contribute to the problem. We cannot make this tragic event more tragic, and we're going to try to do something."

• 9:07Speaker 01

  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 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,

• 9:47Speaker 01

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

• 9:59Ryan 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 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.

• 10:31Speaker 01

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

• 10:45Ryan Holiday?

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

• 10:50Speaker 01

  Would have been much worse.

• 10:52Ryan Holiday?

  And 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 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?

• 11:22Speaker 01

  Yeah, you know, and 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 was going through your mind and whatnot?" I mean, 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 and not to be able to prevent, be unable to prevent an airplane going into the White House, going into the Capitol.

• 12:05Speaker 01

  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 learned that I value greatly.