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RyanHoliday.net - Meditations on strategy and life
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29 Lessons From 150 Million Podcast Downloads

In one of his most famous letters to Lucilius, Seneca gives a pretty simple prescription for the good life. “Each day,” he wrote, “acquire something that will fortify you against poverty, against death, indeed against other misfortunes, as well and after you have run over many thoughts, select one to be thoroughly digested that day.”

One gain per day. That’s it. One quote, one prescription, one story.

George Washington’s favorite saying was “many mickles make a muckle.” It was an old Scottish proverb that illustrates a truth we all know: things add up. Even little ones. Even at the pace of one per day. Because, as the Stoics would say, it’s the little things that add up to wisdom and to virtue. What you read, who you study under, what you prioritize. Day to day, practiced over a lifetime, this is what creates greatness. This is what leads to a good life.

Obviously, that’s what I’m doing with my daily emails (​Daily Stoic,​ ​Daily Dad​), but it’s also just the way I try to live. Every time I listen to a podcast or record one myself, I try to walk away having grabbed at least one little thing.

Over the last several years, I’ve had the chance to spend thousands of hours interviewing people for The Daily Stoic Podcast (which ​you can subscribe to here​ and ​check out on YouTube here​). And with over 150 million downloads so far, the people I’ve gotten access to have been beyond my dreams. I am certainly better, smarter and wiser for the privilege.

So in today’s email, I wanted to share some of the absolute best things I have learned that I think are worth passing along…

This is the best way to grieve. During ​my conversation with Francis Ford Coppola​, he shared that he had just recently lost his wife of 60 years. In coping with her loss, he came across a Marcus Aurelius quote that lifted his spirits. If you lose a loved one, it said, honor them. “My wife was very good,” he explained. “If someone was alone or sick or something, she’d call them up and be comforting to them. And I’m not like that, you know? So I started to do that. People that I know, some guys my age who have no grandchildren, I call them up and say, Hey, how are you? And they are so pleased and so kind. And that’s how I keep my wife in my life.” It was a wonderful conversation–seriously one of the best I’ve ever had–so ​if you haven’t checked it out, give it a listen here​.

Find your reps. Lacrosse legend Paul Rabil had a coach tell him that the key to making it in lacrosse was simple: take one hundred shots a day. The caveat? Holidays, bad weather, sickness–none of that can get in the way. “You can’t miss a day,” the coach said. And that’s what Paul did. Every single day from high school through his professional career–for twenty years. Everywhere he went, he found a wall to throw against, a goal to shoot on. One hundred shots a day, no exception.

I like that idea because it translates to almost everything in life. Whatever sport, business, or field you’re in: figure out what your reps are. Something you can commit to, every single day, that’s completely in your control. The key is: never miss a day. (​Listen to the full interview with Paul here​, and check out his book ​The Way of the Champion​.)

Be an ‘everyday guy’. ​Buzz Williams​, the basketball coach for Texas A&M, brought up a similar point. He talked about the idea of being an everyday guy: “Whatever it is that you’re trying to do, are you tough enough to do that every day?” he asks. “If you’re basing it on talent, well at some point in time it might prevail, but not always. And so if you remove talent, then it comes down to consistency, discipline, and how you are spending your time.”

Dress for success. Speaking of Buzz Williams…One of the benefits of being a writer is that I can dress how I want: tshirts, jeans, shorts, whatever. But when one of my favorite guests (Buzz) ​was coming out to record an episode​, I figured I’d dress up for him. Of course, Buzz showed up in basketball shorts and a tshirt. It made me laugh because in ​Discipline Is Destiny​, I have a chapter called “Dress for Success”. In it, I wrote about General Zachary Taylor, a General who notoriously hated wearing a uniform. Yet when he met with a naval officer, Taylor dressed up to make his guest more comfortable. Meanwhile, the naval officer, in a gesture of respect for his peer’s humble style, came in civilian dress! It’s just a reminder that just because we don’t put much stock in superficial things doesn’t mean that other people’s impressions don’t matter. Presentation counts…and so do other people’s feelings. It’s good to keep this in mind in life. Anyway, you can see what I’m talking about by ​watching the interview on YouTube​.

Remind yourself what really matters. Grief and loss expert David Kessler has spent serious time with people on death’s door. One of the most impactful experiences he shared was when he was at the home of someone in the last few moments of their life. They were surrounded by friends and family and one of the friends asked if they wanted to see their new car, which was parked outside in the driveway. The dying person said no, they didn’t care to see the new car. “How ridiculous was that concept all of a sudden?” David Kessler said. “You just realize everything that what we thought was going to make us happy and become how we identify ourselves just means nothing. It means nothing. What matters is the people, it’s the love, it’s everything else.” ​This was a hard-hitting episode that everyone would benefit from listening to​.

Fall in love with the moment. Dr. Michael Gervais is the world’s leading performance psychologist. He says that the remedy to the anxieties of a new project, a growing to-do list, an uncertain future, is falling in love with the present moment. ​“As opposed to being anxious, protective, trying to control stuff, can you just be in love with showing up and experiencing this moment?”​ Too often, we refuse the gift of the moment in front of us. We dwell on what’s long behind us, or anxiously project ourselves into an imagined future—either yearning for it or dreading it. But if you care-take each moment, you’ll experience an instant lightness–a feeling you can have all the time if only you can get out of your head.

You’ll almost always be improved by this one thing. I wrote a whole book about slowing down (​Stillness Is The Key​), so when Cal Newport’s new book, ​Slow Productivity​, came out I was so excited to read it and talk with him about it ​(please read it, it’s so good​). One of the things ​we talked about in his episode​ is the importance of taking walks, not only for your mental and physical well-being, but because it actually stimulates productivity: “The motor neurons involved in walking act as a dampener on neural noise (those distracting thoughts),” he explains. “When you’re sitting still, sometimes the problem is there’s not enough dampening going on in your brain so it becomes hard to sustain your focus. When you’re walking, it puts on some cognitive blinders and you’ll find it’s easier to hold your focus on an abstract idea.” You can ​watch the whole clip of this part of our conversation here​.

Keep a physical practice. Earlier this year, I was lucky enough to swim in some of the best pools in the world while on tour in Australia (by the way–​I’ll be in London, Rotterdam, Dublin, Vancouver and Toronto in just a few weeks, so get tickets here​). I was reminded of ​a wonderful conversation I had with Bonnie Tsiu ​about her incredible book, ​Why We Swim​: “We are biologically driven to respond to certain set points in the environment—our brains love to be near water and blue spaces,” she said. “We love immersion and the feeling of physically being in water because our brains produce more alpha waves—those wavelengths associated with relaxation, calm, and creativity—when we are merely listening to or looking at it. There is a benefit to both body and mind to get in and swim.” It’s just another reminder that having a physical practice is essential to the creative life (​as I write about here​).

Nobody can ‘make you’ upset. ​A reminder from Timm Chiusano​ for the next time you open your inbox to a nasty email, or you’re passed over for a promotion, or your co-worker throws you under the bus at the meeting: “You’re complicit when somebody else says something and you’re like, ‘I take offense to that’ or ‘I’m so annoyed right now.’ If you’re able to actually accept that that is true, that you’re complicit in those situations, do you know how much stress that you’d relieve for yourself in corporate America on a day-in and day-out basis? It’s nuts. That’s like 90 percent lift of weight off your shoulders.”

You just have to accept it. ​Former U.S. Senator Martha McSally​ (and first American woman to command a fighter squadron in combat) on overcoming obstacles: “Stop resisting what is. We spend a lot of energy resisting what is, whether we don’t like our boss or the relationship we’re in, and we really want other people to change. If we can accept what is, then you can address what is, then you can address the things that are in your control to actually create the life you want, the relationship you want, the situation you want.”

Have fewer of these. I’m an adamant proponent of having less opinions. ​I’ve talked about it​ and written about it for ​Daily Stoic​ and ​Daily Dad​. I really liked the way ​Renee DiResta frames it​ in the context of getting angry at something online: “You don’t actually have to do anything. You can let it go by. What an incredible experience it is to let someone be wrong on the internet without weighing in on it.”

Be YOU. ​Rainn Wilson shared a story​ of a painful period when he was trying to be someone he wasn’t. It was 1995 and he was cast in his first Broadway play. In his head, he had this preconceived notion of a Broadway actor: very professional, very serious, very matter-of-fact. Rainn tried to be that person. “And guess what? I sucked,” he said. Night after night, for the entirety of the six-month broadway run, “I sucked. And it was a miserable six months. There’s nothing worse than knowing what you are doing is terrible…And when I finished the play, I said, Never again. Never again am I going to do that. I’m going to find my authentic voice as an actor. I’m quirky, I’m kind of weird—I’m going to embrace that. I’m not going to try to be something to please someone else. I gotta be me. And I really just changed how I was as an actor at that point.”

Not long after he made the decision to embrace being himself, Rainn landed not only the biggest role of his career, but what would prove to be one of the most iconic characters in the history of television: Dwight in The Office. “I never would have gotten Dwight had I not gone through the suffering on that play. Because getting Dwight was embracing my nerdy weirdness. If I hadn’t totally embraced that, I wouldn’t have gotten the role of Dwight.”

When we are ourselves, we have value. ​Gary Vee said something similar to this​: “The people that really lean into themselves, like really don’t try to put other things on a pedestal, other people, other opinions and just get really comfortable with the purest form of them? Yeah. Those are the people that have impact, because that’s where the uniqueness—the way you say things, the analogies, the stories, the interpretations, the subtle observations that are unique to you—come out.” No one has ever been like you before. No one will ever be like you again. So why would you copy other people? Why would you try to be like someone else? That’s where the fun is (you don’t have to fake anything). That’s where the value is (when we are like everyone else, we are replaceable—by definition). You should be you. That’s your monopoly. That’s your edge.

Be careful who you admire. “A good chunk of these people are just maniacs,” ​Morgan Housel pointed out on the podcast​. “They’re either fundamentally broken or wounded in some way, or their success is a byproduct of some profound dysfunction.” The most glaring example, he says, is Elon Musk. “He’s achieved some of the greatest success of any entrepreneur, but the same personality traits that got him there are the traits that lead him to do things people hate.” Fighting with random trolls online, getting into spats with journalists and politicians, that’s the same person we glorify for his genius. “Bill Gates was the same. Walt Disney was the same. Steve Jobs was the same. They’re all maniacs at their core. That’s why they were successful.”

You’re stronger than you think. I was thrilled to have Dr. Becky Kennedy on the podcast because her work has impacted me in innumerable ways. If you haven’t read her book, ​Good Inside​, yet…what are you doing?! ​We had an incredible conversation that every parent–or really just any human–needs to listen to​. In the episode, she says that anxiety is “some amount of uncertainty coupled with our underestimation of our ability to cope.” It reminded me of one of my all-time favorite Marcus Aurelius quotes: “Remind yourself what you’ve been through and what you’ve had the strength to endure.”

Get clear on what you want. ​Productivity expert Ali Adbaal​ consolidated 90% of the world’s productivity advice into three points: “Number one is figure out where you actually want to go. Number two is to convert all of those goals into words. So if you’re trying to write a book, your goal could be to write 500 words a day. And three is to just put it into your calendar and hold yourself accountable.”

Amateurs love tools. To that note, ​we also talked about how amateurs are obsessed with tools​, but the only thing that’s actually going to get you anywhere is sitting down and doing the work. You can have the best software in the game, but if you’re not willing to do the thing you’re trying to do, day in and day out, you’re never going to get anything done.

More on thoughts of tech tools…​I asked Robert Greene what he thought about Artificial Intelligence​. He said: “I study a lot of languages. That was sort of my major in college. I think back to the moment when I was 19-years-old and at Berkeley. I remember they gave us a passage of Thucydides, the hardest writer of all to read in ancient Greek. So I had this one paragraph and I must have spent ten hours trying to translate it. Finally, I think I have the answer, so I turned it in to my professor and he said, ‘Robert, you were almost there, but you missed it. You completely mistranslated this beautiful paragraph. But,’ he said, ‘you were getting at something.’ And that had an incredible impact on me. Even to this day, it has developed character, patience, and discipline. You’ve got kids nowadays who are never going to have that experience. These incredible skills that the brain has are going to be atrophying, I fear. The brain is so much more interesting to me than any piece of technology. That’s what we should be worshiping, not these little toys that we create.”

Show, don’t tell. ​Austin Kleon​ on parenting​: “You have to be the kind of man that you want them to be. You have to become the kind of human being that you want them to become.” ​Marcus Aurelius​ was talking about being a human being: “Waste no more time arguing what a good man should be. Be one.”

Build the damn frog float. Early in his Seal training, ​Admiral McRaven​ was called to meet with his commanding officer. Thinking he was about to be sent on a mission, he rushed to the office. When he got there, the chief officer asked him to build a frog float for a local parade.

It was in his disappointment that he was given the best advice he’s ever received: “I bet you thought you were going to be jumping out of airplanes, blowing things up and saving the world!” Senior Seal Herschel Davis said to him later that day. “Let me tell you something, I’ve been in this canoe for thirty years. If the skipper wants you to build the frog float, then you build the best damn frog float you can.”

“Ryan,” ​McRaven said after retelling this story.​ “We all get these jobs that we believe are beneath our status. But if you take the job on and you do it well, one: people will think you are good enough to do the bigger job. But I also think you have a responsibility when someone gives you a job, to do it the best you can. Throughout the course of my career, I had to build a lot of frog floats.”

The important thing is not to be afraid. I’ve talked to a couple professional baseball players on ​the podcast​ (​James Outman​, ​​Ian Happ​​, ​​Scott Oberg​) as well as professional basketball players and coaches (​​George Raveling​, ​Chris Bosh​​, ​​Cuttino Mobley​​) and entrepreneurs (​​Tim Ferriss​​, ​​Rob Dyrdek​​). One thing they’ll all tell you is that a person who is afraid to strike out, afraid to miss, afraid to fail is a person who will not succeed.

Focus on the effort, not the outcome. Speaking of Ian Happ…​he shared the story​ about the time he got sent back to the minor leagues after a great rookie season with the Chicago Cubs in 2017. The reason? He was too worried about the things he couldn’t control: “When you worry about the things that might get you put on the bench, the end result of that is always, you do the things that get you put on the bench,” he explains. “Instead of wondering why or trying really hard to impress a coach or the people who make the decisions, I said, ‘you know what? I’m going to believe in myself, put in the work, and at some point, they’re not going to be able to keep me out of the lineup.” This mindset got him back into the Cubs’ lineup with a breakout season, and ultimately landed him on first MLB All-Star team. It was only when he cared more about what he was doing (and less about what others were thinking) that he was able to really perfect his game.

Guard your time. ​The novelist Philipp Meyer​ (whose book ​​The Son​​ is an incredible read) ​said​, “You have to be very careful about to what (and to whom) you’re giving the best part of your day.”

Tempus fugit (time flies). ​Professor Scott Galloway told me​ about the profound grief he felt looking at a picture of his 11-year-old, who was now a great 14-year-old. The 11-year-old, Galloway realized, was gone for good. Every parent’s deepest fear is losing their child. And the terrible, beautiful tragedy of parenthood is that, indeed, we are constantly losing our children. Day, by day, by day. Not literally, of course, but in the sense that they are constantly growing, changing, becoming someone different. On a daily, if not an hourly, basis.

Forget about competition. One of the things that fascinates me about Tim Ferriss is his ability to spot something before anyone else. ​He explained this philosophy on the podcast​: “When I find an area that is crowded or competitive, I look at that as an opportunity to find something that is uncrowded. Podcasting has become incredibly competitive, so instead of trying to fight for space, I’d start to look for what’s neglected.” Not only does this help to limit comparison, it’s also a brilliant business strategy (there is a wonderful book on this called ​Blue Ocean Strategy​).

There’s no such thing as being “self-made”. On the surface, Arnold Schwarzenegger’s life story is a classic example of that idea of the “self-made man.” Born and raised in a small village in Austria, seemingly on his own sheer will and determination, Arnold achieved extraordinary success in the worlds of bodybuilding, acting, business and politics, ultimately becoming a global icon. ​But, he told me,​ he didn’t do it on his own. “I have been a creation of hundreds of people,” he said. “Thousands of people. It’s unbelievable the amount of people that helped me and pushed me,” he said. This is true for all of us, we are all the sum of our surroundings, the products of our influences, our environments, our family and friends. Success is a collaborative effort. Doesn’t that make it more wonderful? ​This was one of the craziest episodes I’ve ever filmed (I flew to LA to record it). If you’re going to tune into this episode, definitely watch the video here​.

The Obstacle Is the Way. After running 100 miles in less than 24 hours, ​Nate Boyer told me​, “the worst part was the expansive flat portions without the ups and downs — there might be a life lesson in that.”

Exercise this muscle. The mental performance coach ​Greg Harden​​ worked with Tom Brady and Michael Phelps, (among countless other top performers) had a great line: in the way that the ability to quickly recover after a workout is an indicator of physical fitness, “People who are mentally fit recover faster than the average person.”

This is life. In 2017, ​I interviewed the writer and Southern Stoic, Peter Lawler​. He passed away a short while after. We had the great ​Paul Woodruff on the podcast to talk about his love of Marcus Aurelius​, and we didn’t even know that he was dying of bronchiectasis. Just last year, ​we interviewed the indelible Dr. Sue Johnson​, who wrote the must-read ​Hold Me Tight​, and she sadly passed away this April. ​Greg Harden came out to the podcast last year, too​. Just a little over one week ago, he passed away.

​The Daily Stoic Podcast​ hasn’t been around that long, but guests whose work has had an enormous impact are gone, already receding into memory. This is a great Stoic reminder. None of us last forever, none of us are invincible, none of us are exempt from death.

We have to notice this. We have to think about this. Because we can’t stop death from happening. We’re all marked souls, living on borrowed time. Let’s not waste what time we have left.


October 30, 2024by Ryan Holiday
Blog

Everything I Learned From Iron Maiden About Life

What does Iron Maiden have to do with Stoic philosophy?

Nothing really, but this is my newsletter and it’s what I want to talk about.

I’ve been an Iron Maiden fan since I was a kid (more about how I found them below). I’ve seen them live in Sacramento, Los Angeles, Austin and San Antonio (2x). If you’ve ever seen me on a podcast or in a ​Daily Stoic video​, if you’ve come to ​one of my talks​ or bumped into me in person…there’s a very good chance you saw me in an ​Iron Maiden t-shirt​. I even wrote about them in my book ​Perennial Seller​.

But mostly, what inspired this piece is that I am taking my 8-year-old to see them later this month…exactly twenty years after I went to my first Iron Maiden concert.

So what have I learned in two decades of an unhealthy fandom of a British heavy metal band?

A lot.

Let me tell you.

Know what business you’re in. There is a story about the manager of Iron Maiden, Rod Smallwood, who has worked with the band since 1979. He is at a dinner honoring the group. A young agent comes up to him and says how much he admires his skillful work in the industry. The manager looks at him and says, “HA! You think I am in the music business? No. I’m in the Iron fucking Maiden business.” The publishing industry? The retail business? These are not the businesses I am in–just like you’re not in the coffee industry or B2B. No, you’re in the business of you. You’re in the business of serving your customers in your city with your unique offering. The trends of the bull or bear market? It doesn’t matter, just as the trendiness (or lack of trendiness) of heavy metal hasn’t mattered to Iron Maiden. What matters is their relationship with their fans. That’s who they are in service of. That’s the job. And so it goes for all of us, whatever we do.

Develop range. Bruce Dickinson, the lead singer of Iron Maiden, has incredible range. I don’t mean his voice (though it’s very impressive). I mean that he has done more than just sing in a band that’s sold millions of records. He’s done more than have a decent solo career. He wrote a couple of popular children’s novels. He became an Olympic-level fencer (seriously, nearly making the British Olympic team). Oh, and then he learned how to fly planes…like really big ones. Here’s a picture of the Iron Maiden plane…which he flies after the band performs, taking the group to their next gig.

That is preposterous! The only thing more ridiculous is that for many years he also worked for Astraeus Airlines and ​once airlifted British tourists stranded in Egypt​. It’s one thing to master one skill, but to master a couple different domains? That’s hard. But it pays off. Because we learn skills and are introduced to new ideas that we can bring back to our main thing (a bunch of the best Iron Maiden songs are about flying…and swords). A book recommendation in this regard is David Epstein’s book, ​Range: Why Generalists Triumph in a Specialized World​.

Create spectacles. The “Ed Force One,” as they call the Iron Maiden plane, is not just a mode of transportation—it’s a flying billboard, a conversation starter, a part of the Maiden mythology. Wherever it lands, it captures attention, sparks curiosity, and draws people into their world. Are there cheaper, more efficient ways to travel on tour? Probably. But that’s not the point.

I always think about spectacles (albeit on a much smaller scale). When we were setting up ​The Painted Porch​, that blend of function and spectacle inspired one of the best decisions we made—making ​our book tower​. It’s 20 feet tall and made of some 2,000 books, 4,000 nails, and 40 gallons of glue. It was not cheap to do. It was not easy. It took forever. We had to solve all sorts of logistical problems to make it work. But it’s also probably one of the single best marketing and business decisions we made in the whole store. Because it’s the number one thing people come into the store to take pictures of.

Focus on what’s in your control. Ok, maybe there is one Stoic lesson. As you know, the core of Stoic philosophy is focusing on what’s in your control. It’s about ignoring what other people do and say and putting that energy into what you do and say. Bruce Dickinson explained Iron Maiden’s philosophy: “We have our field and we’ve got to plough it and that’s it. What’s going on in the next field is of no interest to us; we can only plough one field at a time.” Do you…you’re the only one who can. It hasn’t always been easy, but I’ve tried to remind myself that it doesn’t matter how many books other people sell. It doesn’t matter what anyone else is doing. I’m writing about an obscure school of ancient philosophy. It has its own ceiling and its own floor. I’m comfortable with that.

Success and fame are byproducts. It’s fair to say that Iron Maiden is a cult act rather than a mainstream act. And yet, it’s a very big cult. They’ve sold millions of records. ​Here’s a video of them performing in front of 250,000 people​. The point is: The band is famous. But what is fame? Marcus Aurelius would say that it’s nothing–the clapping of hands and the clacking of tongues. Actually, Bruce Dickinson has a better quote, I think, because unlike an emperor, their fame was slightly more meritocratic. “Fame is the excrement of creativity,” Dickinson once said, “it’s the shit that comes out the back end, it’s a by-product of it.” So yeah, chasing fame is not only not really worth it, but you don’t get it by chasing it either. An audience, a reputation, fame, these are ​lagging indicators​ of years of making stuff that people like and get to know you through. It’s the byproduct of doing the work.

Build a resilient career. As a British heavy metal act, there’s naturally a bunch of Churchill cameos in their work. It’s fitting because Maiden’s career bears some resemblance to Churchill’s approach to building a resilient career. In ​Perennial Seller​, I tell the story of how Churchill maintained influence even when exiled from politics in 1931. Unlike an ordinary politician, who would have been powerless when voted out of office, Churchill had something more valuable than office—a platform. Between 1931 and 1939, during his so-called political wilderness, he published 11 books, 400+ articles, and delivered more than 350 speeches. The result of this was an enormous worldwide platform that allowed him not only to survive financially but wield influence that kept him relevant and guided policy and opinion across the globe. This is not unlike Iron Maiden, whose platform transcends the typical constraints of the music industry. Instead of relying on album sales or radio play, they created a multi-faceted empire: elaborate stage shows, their iconic mascot Eddie, comic books, video games, and even their own beer. It’s what’s solidified them as a perennial force in the music industry, enabling them to endure fads and technological shifts. Of course, it’s meant financial success, but what’s even more impressive is that their platform frees them to communicate to their fans without interference from intermediaries and allows them to create work on their own terms.

Respect the boundaries. What’s interesting is that despite all Bruce’s range and all the decades Iron Maiden has made music, there’s not a huge difference between their first album and their most recent, Senjutsu. Basically–and this includes the different lead singers–Iron Maiden has been following the same formula on all their albums for the last 49 years. I don’t think that’s an insulting thing to say–it’s no small feat. It’s also something they’ve done on purpose. As Bruce has explained,

“There is an unspoken contract between the band and the audience. If you’re David Bowie and your fans want you to change every album then that’s his style. With Maiden, that’s not our style, fans like us to play something that’s identifiable; they want to see nuances of change but they’re happy with Maiden. Maiden’s music appeals to a certain person and in every generation there’s a certain amount of those people born, that’s why Maiden’s appeal is finite in terms of the number of records we sell in the short term.”

I know what my audience expects from me. I don’t find that constraining, it’s actually liberating. One of the Stoics, Cleanthes, would talk about how the ‘fetters’ of poetry actually unlock creativity–I think that’s true. You establish a contract with your audience, an expectation of the medium, and you have to deliver on that. The freedom is in the how.

What matters is that it’s interesting to you. On some level, Iron Maiden’s songs are absurd. Music is supposed to be about stuff that people relate to–falling in love, growing up, partying, having fun. Iron Maiden writes 10-minute songs about literature and history. They have songs inspired by Coleridge poems, science fiction novels, historical figures like Genghis Khan and Alexander The Great. They’ve got a song about Passchendaele (one of the most horrific battles of the First World War) songs about D-Day and the Crimean War. Steve Harris, who writes most of the band’s songs, clearly loves to read. Which is the point–he finds these things very interesting. And as a result, they become very interesting to the audience. Again, on the surface, an obscure school of ancient philosophy should be pretty boring. My publisher and most of my friends suspected it would be…but my passion for it was contagious.

Build on greatness. They don’t just write songs about ancient history. They’ve got songs based on lines from Shakespeare, the ​epic novels of Frank Herbert​ and the myth of Icarus. It’s very hard to do better than Tennyson or Coleridge (a poem of whose Iron Maiden has a 14-minute song about), so don’t fight it. Or what about Aces High, for which the music video opens with Churchill’s greatest speech? Iron Maiden is very good at incorporating great works of art into their art. Never underestimate the power of repackaging something timeless and old. In my teens, I discovered so much stuff through Iron Maiden. None of my teachers read us ​The Charge of the Light Brigade​–I heard it from Iron Maiden (my son can recite a big chunk of the poem now). I read ​Brave New World​ because they have an album based on the book. I’ve taken a lot of joy out of paying that process forward in my own books, finding stuff that I love, that I think is great and introducing people to it.

Make it a universe of true fans. There is a theory put forward by Kevin Kelly, the founder of Wired magazine. He calls it 1,000 True Fans: “A creator, such as an artist, musician, photographer, craftsperson, performer, animator, designer, videomaker, or author—in other words, anyone producing works of art—needs to acquire only 1,000 True Fans to make a living.” Iron Maiden is this idea on a massive scale. Somebody once joked that Iron Maiden has sold more t-shirts than albums. If that’s true, it’s no small feat (the band has sold over 130 million albums) and not exactly a bad thing (you make more money on merch than music). But I think that’s why I’ve always liked the band. It’s not just music but a whole universe of art and imagery and themes. There’s even a phrase that the fans say to let each other know their identity: Up the Irons! This is something I thought a lot about with ​Daily Stoic​. I don’t just ​write books​, but I have ​designed​ and ​made things​ that continue that experience in many ​different mediums​. It can’t be, as Lady Gaga warned, “Thanks for buying my record, fuck you.” It should be, “Oh, you liked what I did? Here’s a bunch of other cool stuff that I designed for people just like you.” Don’t stop at the surface with what you’re building–make it a world. Better yet, make it a universe of hard-core, true fans.

Backstage of the Tamron Hall Show

Find ways to spread. When I was on ​Jocko’s podcast last year​, he asked me how I became an Iron Maiden fan. ​As I explained​, I was trying to illegally download a Metallica album and ended up with an Iron Maiden album. But then again, how else was I going to discover them? It had been years since they were on regular rotation on MTV and unlike Metallica, rarely got radio play. Solving the problem of discovery is the thing all arts and companies have to figure out. Sometimes traditional avenues are open, but often they are not–or they are very clogged. When Iron Maiden sells out a stadium in Brazil or Colombia or India, how do you think most of those fans heard about them? In a lot of cases, it was via bootlegs. It was YouTube. The same is true for writers. Obviously, piracy is not ideal. It would be better if everything was legitimate and affordable. But that’s not the case. If you want to maintain relevance and sustain an audience, you have to embrace these other channels. You can’t sweat every YouTube upload or every time someone rips you off. In fact, you can appreciate that what it’s doing is adding to the universe you’ve created. There’s a reason I give away the vast majority of stuff that I make–I want to find its way to people, I want the barriers of entry, of discovery, to be as low as possible. You never know what kind of journey you might kick off for someone who comes across your stuff.

Play the long game. Iron Maiden has been at it for nearly 50 years and counting! They’re playing the long game, defying every stereotype in the music business. 17 studio albums, 14 live albums, 2,000 concerts in 59 countries, over 130 million albums sold. They performed for 250,000 people as the headliners of the Rock in Rio festival—26 years after the band formed. This empire wasn’t built on one hit album or a viral single. It’s the result of applying a perennial seller mindset to everything they do. It’s easy to chase quick wins, but Maiden reminds us that real magic happens when you zoom out. When I first started listening to Iron Maiden, I remember reading that they had sold something like 50 million albums. That was a lot then, but what’s amazing is that twenty years later, that number has almost tripled. Do you know how insane it is to sell that many records these days? But that’s the thing–time and momentum are incredibly powerful forces. In the beginning, small efforts might seem insignificant. But they accumulate and compound over time. Whether it’s a decades-spanning discography, a business, a career or an anthill, impressive outcomes start with humble beginnings.

The more the merrier. In 1990, Adrian Smith, one of the band’s best guitarists, left the band. He was ably replaced by Janick Gers for 9 years, until Adrian asked to rejoin the band. There is something special about original lineups so you might expect that Gers left the band, but nope. The band just switched to having three guitarists! And why not? It just means more guitar solos for everyone! Is there an applicable lesson here? I dunno, I’ve just always liked it.

My Iron Maiden Christmas sweater

Just keep going. How has Iron Maiden lasted through the years? It wasn’t just by making great work—it was by making a lot of it over and over again. Some of Iron Maiden’s greatest songs are on “Brave New World” (released 25 years after the band was formed) or “Dance of Death” (released 28 years in). It’s easy to be intimidated by success, or to be made complacent by it or to give in to the fan’s reverence for the past. But it’s better for you and your art to put those feelings aside, to keep trucking along, to keep making stuff. When I first heard Iron Maiden in 2001, they had already been going for 26 years at that point. And they’re still going! Every time I see tour dates, I get nervous and tell myself, I should probably catch them one more time. That’s what I did on this tour and then you know what I saw? They announced another tour for 2025. But that’s the thing when you make great, perennial work–it creates momentum for you to keep going. Not only that, it means it will live on well after you stop.

I’m nearly two decades into my career. Sometimes I get tired, but that’s when I remind myself that I have a lot further to go, that I’ve got a lot more in me. Just keep going. Maiden taught me that.

Iron Maiden shoes backstage of The Daily Show

October 2, 2024by Ryan Holiday

“If you only read the books that everyone else is reading, you can only think what everyone else is thinking.” - Murakami

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