Insight
Holiday argues decades of corporate conformity permanently destroys visionary leadership potential.
“The system is shaping you every day that you are in it. And you are internalizing its values and its personality and its identity. And the idea that, like, yeah, that you're gonna go along to get along for 40 years and then be a visionary, rule-breaking leader…”
Assertion Not checkable as stated
Holiday: Every Retired Pro Athlete Regrets Not Enjoying Playing More
“There's not a single athlete That you've, you will ever talk to who's retired, who doesn't say something like, I wish I enjoyed playing more, because at some point it just goes away, and then at that point the winning and losing stops mattering, and all they t…”
Insight
Holiday argues ed-tech shortcuts fail because true learning requires difficult friction.
“I think sometimes we look for technological solutions to make things easy, and the whole point is some things are supposed to be hard. You know, it's supposed to be difficult, and it is in the difficult part that you're scratching it into the steel, and then i…”
Insight
Holiday: Historical Accuracy Matters Less Than Moral Lessons in Kids' Stories
“Whether they're true or not is much less important to me than whether they have some kind of moral lesson that sticks with them that, by the way, when they get into situations in life I can be like, this is like that thing that we learned about.”
Insight
Holiday: Pursuing an enduring posthumous legacy has zero value
“I think a lot of people, they spend all this time trying to create this, not just success now, but this monument that endures for all time, as if that's of value. Like, it isn't. It's not only something you don't control, even if it was guaranteed. It doesn't …”
Insight
Holiday: Ancient Stoicism was repetitive practice for crisis, not abstract theory
“We tend to think of philosophy as, like, theoretical and abstract and very high-minded, but for the ancients, it was this kind of thing that you practiced and you went over, over, and over again so that, like, in big moments, like, when you have a big life dec…”
Disclosure
Holiday instructs his assistant to keep commitments off his calendar.
“Their job is to keep things out of the calendar, not put things in the calendar. Like the calendar should have large amounts of white space in my opinion.”
Insight
Holiday: Sacrificing Present Well-Being for Uncontrollable Future Payoffs Is Dangerous
“The idea that the shit now Is worth enduring because it will be amazing later is a dangerous thing to fool with, right? Not just because you might not get later but because you don't actually control whether later happens. And I, by that, I don't mean you coul…”
Insight
Ryan Holiday: Successful people never feel like they have truly arrived
“If you talk to successful people, nobody ever gets, and I don't mean that they're never successful. I just mean nobody feels like they arrived, that they finally got, you know, more out of it than they put into it. That never happens.”
Opinion
Holiday calls Buffett reading 'The Intelligent Investor' history's best investment.
“Like, you think, like, Warren Buffett is told to read The Intelligent Investor by Benjamin Graham. And, you know, that's probably the single best investment in human history. You know, like, he reads this one book, and he makes a hundred billion dollars.”
Insight
Holiday argues listening to audiobooks at 3x speed destroys true comprehension.
“To really understand something, you gotta spend a lot of time with it. It can't be, I think people are always looking for shortcuts, you know, and they're like, oh, I read this on three X speed on audiobook, and you're like, I don't know if that's, I don't kno…”
Insight
Ryan Holiday: Ego turns a leader's assets into liabilities
“There's this point where all the assets the person has turn into liabilities, and ego is usually like the swing vote in that.”
Insight
Holiday: Online detractors criticize charity to excuse their own inaction
“What they're trying to do is, is denigrate the good that you are doing so they don't have to feel bad about the nothing they are generally doing. They're trying to go, if I cancel this out, then we're even, and then I don't have to feel, you know, like, compel…”
Insight
Holiday argues social media extracts unpaid emotional labor by provoking discomfort.
“Social media Is dependent on your unpaid labor, emotional and otherwise. Like, it is designed to make you uncomfortable, or provoke you into clicking, reading, or posting, or watching, or whatever it is, and that, like, it's really good at that.”
Opinion
Holiday claims Marcus Aurelius would be completely forgotten without the movie Gladiator.
“That's one of the most famous people who ever lived in their own life, and he's mostly forgotten, and if the movie Gladiator didn't exist, he'd be even more forgotten.”
Insight
Holiday advises public figures to make their media statements untruncatable.
“You always have to be careful about making sure your complete thought is untrunkatable, right? Because the context of it can be stripped out of it.”
Insight
Holiday: Top marketers should eventually create and sell their own products
“If you have, like, real marketing chops, that's what you should eventually evolve towards, is your own stuff.”
Insight
Holiday warns creators that building a following often leads to audience capture.
“I think we work really hard as a creator, an artist, or writer, whatever, to build an audience, and then you think you have the audience, but actually the audience has you, because now you're afraid of losing it, right?”
Disclosure
Holiday keeps zero social media apps on his personal smartphone.
“I don't have any social media apps on my phone.”
Disclosure
Holiday: Research Process Remains Fully Analog for Deep Comprehension
“My research method is as analog and as old school as it can be because I'm trying to actually understand what I'm dealing with.”
Disclosure
Ryan Holiday reveals his books have sold roughly ten million copies.
“My books have sold millions of copies, which I take to mean there are millions of people who don't like me, like not just millions of people who saw this stuff and then decide, like, I would argue more people saw it and decided not to buy it than saw it and de…”
Assertion Not checkable as stated
Holiday reveals the Daily Stoic email reaches one million people daily.
“The Daily Stoic email goes out to a million people every day.”
Disclosure
Holiday: I gave a talk to the Los Angeles Rams on 'panic rules'
“So actually, this came from a talk I gave to the Los Angeles Rams. We were talking about this idea of panic rules.”
Assertion Supported
The US military deployed a backup helicopter for the Bin Laden raid.
“I mean, on the famous Bin Laden raid, they had an extra helicopter because they planned that one might crash, right?”
Ryan Holiday