27 Things I’ve Learned From 150 Million Podcast Downloads

In his letters—the pre-digital medium for distant long-form conversation—Seneca instructs his friend Lucilius to find one thing each day that will fortify him against death, despair, fear, or adversity. Just one thing. One nugget. And that’s what most of Seneca’s letters to his friend are about. They have a quote in them. Or a little prescription. Or a story. But in each case, Seneca is explicit. Here’s your lesson for the day, he says. Here’s your one thing.

Obviously that’s the logic behind the daily emails I write (Daily Stoic and Daily Dad), but it’s also 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. That’s how wisdom is accumulated—piece by piece, day by day, book by book, podcast by podcast.

It’s not much, but considering the scale of The Daily Stoic Podcast, it’s actually added up quite a bit. I’ve interviewed roughly 200 people over the last five years. That’s maybe 300 hours of audio with people who’ve won Academy Awards, the Super Bowl, and sold millions of records. I’ve also probably appeared on ~250 shows myself since my first book came out in 2012. Here’s a list of stuff I have learned that I think is worth passing along…

– 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.”

– When I interviewed Gretchen Rubin, one of the most thought-provoking and influential experts on happiness, she told me about one of the things she learned from her former boss, the Supreme Court’s first female justice, Sandra Day O’Connor. Shortly after Gretchen published The Happiness Project, she asked O’Connor who she had clerked for, what is the secret to happiness? O’Connor replied, “The secret to happiness is work worth doing.” Perfect.

– Something I’ve started implementing from Adam Grant: in addition to coaches and mentors, you need to have judges. Adam was a competitive springboard diver growing up, “and I found it enormously helpful to get a 0 to 10 score every time I came out of the water.” When he transitioned from sports to the work world, he found it hard to get useful feedback. “So I started asking people—I would give them drafts—and I’d ask, ‘can you rate this 0 to 10?’” After a presentation—what would you score that 0 to 10? After giving a talk, after leading a meeting, after publishing a newsletter, whatever—ask, can you score this 0 to 10?

– I got a cold plunge tub after talking to Joe Rogan on his podcast. Before then, I thought all the data about the physical benefits of taking cold plunges was mostly bullshit. But Joe talked about the mental benefits—“Difficult things are good for you,” he said. “They’re good for your mind.” It echoes Seneca: “We treat the body rigorously so that it will not be disobedient to the mind.”

– The famous philosopher Diogenes the Cynic was once seen begging for money from a statue. What on earth are you doing, someone asked. “I’m getting practice in being refused,” Diogenes replied. I’ve talked to a couple professional baseball players on the podcast (Ian Happ and Scott Oberg are both must listens) as well as professional basketball players (Chris Bosh and Cuttino Mobley) and entrepreneurs (Tim Ferriss and 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.

– 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.”

– My wife Samantha and I started recording conversations (here, here, here, and here) for The Daily Dad Podcast, and it’s become one of my favorite podcast formats. We talk about things we’re working on as parents, how we can better support each other, tips we’ve picked up from books or from other parents, phases our kids are going through, how to handle and adapt to those phases, and really just all things parenting.

The mental performance coach Greg Harden (who has 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.”

– The serial entrepreneur Kevin Rose made a good point about how things don’t just cost you monetarily. They cost you mentally too. “The thing that I’ve realized is that every object I own, every thing, is a subconscious mental burden. Without a doubt. It can be the wheel-barrow that has a flat tire sitting out in the backyard—some part of me is thinking about how I know I have to figure out how to get that fixed at some point. So I’ve reduced the stuff that I have by an order of magnitude.”

– In August of 1967, Lieutenant Dave Carey was shot out of his A-4 Skyhawk over Vietnam. Soon enough, he found himself a prisoner in Hanoi, where he would subsequently be beaten, tortured and placed into solitary confinement. For six years, he languished there, kept going only by the comrades around him, and an occasional pick me up from the Stoics. As Carey told me in an incredible episode of The Daily Stoic Podcast, fellow prisoners would tap, “Stockdale wants you to remember what Epictetus said,” from an adjoining cell. Carey came to understand this to mean focus on what you control, focus on the choices you can make.

– Related, I asked Jocko Willink what his advice would be for leaders during turbulent times. “Really, it just comes down to having humility.” It’s immediately and unflinchingly accepting the reality of the situation. Not denying the problem, running from it, or expecting magical thinking to rescue you.

I had an incredible conversation with the historian Heather Cox Richardson, who writes “Letters From an American”—the Substack newsletter with the most number of subscribers. This line stuck with me: “it’s a truism in American history that if you have rights, you plead the Constitution. If you want rights, you plead the Declaration.”

– One of the great perks of my life is getting to have regular conversations with one of the great writers of our time, Robert Greene. We recently decided to record one of those conversations. I asked him about what I think is the thread through all his books, something which is also in short supply these days: an unflinching commitment to reality, even when it’s inconvenient. “Whenever I hold a belief, or I’m writing a book,” Robert explained, “I always start with the premise that I’m probably wrong, that I’m actually quite ignorant, that my idea is pretty stupid. And I look at the evidence on the other side and I examine it and I try to convince myself that my initial idea was right. And if it isn’t, then I change it.”

– The legendary music producer Rick Rubin (we actually did a fantastic double episode with him) talked about why he doesn’t try to chase trends: “I love music that is outside of time. And one of the things about using organic instruments is, a piano a hundred years ago sounds like a piano today and it will sound like a piano in a hundred years. If you use the latest sounds, the newest sounds, the sounds of today—then tomorrow, they’ll sound like the sounds of yesterday…The newest of sounds can quickly sound very dated.”

– In a classic episode of Seinfeld, George Costanza has great success doing the opposite of what his instincts tell him to do. This is now known as The Costanza Principle, and it turns out to be scientifically-sound advice. The positive psychiatrist Dr. Samantha Boardman told me, “There’s so much messaging today about how you always have to be yourself and trust your feelings. But I tell people, ‘be un-you.’ Like, what is the opposite of what you feel like doing right now? Or who is someone you really admire—what would they do in this moment? And I actually think that can get us closer to the versions of ourselves that we would like to be…Separating oneself from one’s impulse, taking a healthy step back and gaining some distance between what you feel like doing and what’s actually going to help you—you’ll make a better choice.”

– At the beginning of my interview (you can listen here) with the peerless Dr. Edith Eger—Holocaust survivor and the author of one of my favorite books, The Choice—I asked her about something I regretted, a relationship I had messed up. She looked at me and said she could give me a gift that would solve that guilt right now. “I give you a sentence,” she said, “One sentence—if I knew then what I know now, I would have done things differently.” That’s the end of that, she said. “Guilt is in the past, and the one thing you cannot change is the past.”

Matthew McConaughey told me why he shut down his production company and his music label. “I was making B’s in five things. I wanna make A’s in three things.” Those three things: his family, his foundation, his acting career.

The great basketball coach Shaka Smart said something similar. He tells his players not to figure out their priorities, but to figure out their priority. “The root of the word ‘priority’ is singular… It was a singular word—the one thing. In modern times, we’ve turned it into ‘priorities,’ but then all of a sudden it turns into eight, ten, 15 things and that defeats the purpose.” Just do one high-quality thing every day, he said; it adds up.

Another from McConaughey. He told me he’s known in Hollywood as “a quick no and a long yes.” What a great expression! Before he says yes to doing a movie, he sleeps on it for ten days to two weeks in the frame of mind that he’s not going to do it. If he sleeps well, he doesn’t do it. If the thought that he has to do it wakes him up at night, he does it.

– Somewhat related: when I did Tom Segura’s podcast, he told me he’s been trying to be a ‘long yes’ when it comes to buying stuff. “There’s a part of buying things that feels good. But I also feel like it’s sometimes good to deny yourself the thing you want in that moment. Instead of going, ‘I want this, I’m gonna get it right now,’ why don’t I give it a month and then be like, ‘do I still want that thing?’ or was that just a passing moment?”

The legendary basketball coach George Raveling told me he sees reading as a moral imperative. “People died,” he said, speaking of slaves, soldiers, and civil rights activists, “so I could have the ability to read.” If you’re not reading, if books aren’t playing a major role in your life, you are betraying the legacy that they left for the generations after them.

– An essential piece of advice I got from the author Steven Pressfield: There are professional habits and amateur ones. Which are you practicing? Is this a pro or an amateur move? Ask yourself that. Constantly.

– Somewhat related, the NASCAR driver and student of Stoicism, Brad Keselowski, talked about what distinguishes a professional in his field (and it applies to most fields). “If the conditions were always perfect, the average 12-year-old could do my job,” Brad said. “The problem is that those days are very seldom.” Can you still show up and perform when the conditions aren’t perfect? That’s the question.

– I was surprised to hear Olympic gymnast Dominique Dawes say that she doesn’t miss or reminisce on being at the Olympics or standing on the podium. “When I dream about exciting moments and memories in my life, those don’t come up… It’s those moments with your family. It’s those moments with your spouse. It’s those moments knowing you planted an amazing positive seed in a stranger’s life. Those are the moments that fulfill us.”

– The great Sam Harris explained something similar. He said it didn’t matter what peak experiences you’d had, what insights you’d been able to come up with while meditating, how enlightened you felt after all the years of practice and study. All that really counted, he said, was what you could muster in the course of ordinary, day-to-day life, or more specifically, in any one present moment.

Austin Kleon talked about being a parent: “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.”

Danica Patrick talked about the surreal reality that’s been her life as an international celebrity. “It made me realize that the stuff that we see—the celebrities, the magazines we pick up—we just think, ‘Oh, they’re famous.’ No, they’re being made famous. Somebody’s paying for that… So early on, I realized that there’s a lot of bullshit out there. And that there’s an agenda behind everything.” This is something I try to remember whenever I see someone getting attention and wonder, “Why am I not getting that?”


What I think is so incredible about podcasts is that other people may have listened to those same episodes and taken something totally different from them. In fact, I know they have because I’ve heard from them. But what gets me excited is thinking that across those hundreds of episodes and now cumulatively over 150M downloads (and many more views on video), that adds up to an unfathomable amount of wisdom that people have been able to add to their lives.

The line from Zeno was that we were given two ears and one mouth for a reason. That reason? To listen more than we talk.

To learn from people who can teach us. To find something that makes us better.

Written by Ryan Holiday