Insight
Holiday: Failing to invest in sustainability costs career longevity, not money
“Because, like, the real cost is not money. It's in how many years of being able to do this it cumulatively deprives you of.”
Insight
Holiday: Passions like anger and fear cause most historical mistakes
“At the root of most mistakes, both personally and sort of historically it's one of the passions, right? Envy, lust, anger, fear you know, pain you know, the, those sort of emotional states that take us out of the rational part of ourselves and into some sort o…”
Insight
Holiday: Self-discipline is defined by self-chosen standards, not legal limits
“Self-discipline is the standard to which you hold yourself. That, to me, that's what moderation is, like, not what you can do, but what you allow yourself to do.
Not what's legal, but what you choose.”
Insight
Holiday: Wisdom governs how and when to apply all other virtues
“Wisdom is not just the pursuit of knowledge and understanding. But particularly the almost intuitive sense of, like, how much courage is required, how much temperance is required, right? What is the right thing? So wisdom, the final virtue is the virtue that k…”
Opinion
Gregory Hays provides the best modern translation of Marcus Aurelius
“Every generation needs its own translation because a book like Mark Ceruleus, he's writing to himself in colloquial personal language. So, when you see, like, thou shall not, that's not, he didn't say that. That's what someone in the Like, 17th century would h…”
Assertion Not checkable as stated
Holiday wrote four books in four years using unsearchable physical notecards
“Yeah, I've written four books in four years. Like, it's not, not having Unsearchable has not held me back in any way that I can currently tell.”
Disclosure
Holiday mandates a $1,500 hourly upfront strategy session for new clients
“All my clients, even ones I know I want to work with, I start with a paid strategy session. Right. So, I charge, like, 1500 bucks an hour and we get on the phone, and, like, you can send me a little bit of stuff, but almost no prep, and then we get on the phon…”
Assertion Supported
Holiday: Elon Musk's friends staged an intervention against founding SpaceX
“When Elon Musk was planning what became SpaceX, his friends held a literal AA style intervention that said, you cannot start a rocket company. This is the worst idea. You will lose all your money.”
Insight
Holiday: Tying joy strictly to favorable circumstances leaves happiness out of control
“I think when the Stoics talk about joy, they are trying to remind you that if joy for you is only possible when things are going amazing, your joy or your happiness is therefore out of your hands.”
Insight
Holiday: Cognitive Distance Makes Advising Others Easier Than Self-Regulation
“We're really good at giving advice to other people and then not so good at applying it ourselves because we have that cognitive distance distance, you know, we're able to It's, our identity is less at stake or our emotions are less tied up in it.”
Insight
Holiday: Financial upside is obvious while opportunity costs are hard to quantify
“The problem is financial upside is always clear. Opportunity costs are sometimes clear, but often not clear.”
Assertion Partly supported
Holiday: Amazon prohibits meetings without pre-edited written memos
“You're not allowed to call a meeting unless you've written a memo about what's going to be discussed at the meeting. And multiple people have to edit that memo before you could sit down and do it.”
Insight
Holiday: Emotional control in high-stakes situations requires prior practice in minor moments
“If you haven't practiced it in the little areas, it's very unlikely you're going to be able to do it. Like when the game is on the line or your career is on the line or like the Eyes of the world are upon you.”
Insight
Holiday: Steel-manning opposing arguments strengthens your own position
“Instead of, you know, reducing your opponent's argument to a straw man this sort of caricature The least you know charitable interpretation of what they think and why, you know, actually really put yourself in their shoes. Try to argue it as well as possible. …”
Insight
Holiday: Prioritizing easier tasks sustains creative momentum during bottlenecks
“In this case, I'm going to do the easier one first because stalling out is the main thing that I want to avoid. It's not that I'm going towards the path of least resistance, but I'm going towards where I'm going to make forward progress,”
Insight
Holiday: Composure during high-stakes crises requires practicing restraint in low-stakes moments
“If you haven't practiced it in the little areas, it's very unlikely you're going to be able to do it, like, when the game is on the line, or your career is on the line, or, like, the eyes of the world are upon you.”
Insight
Stoicism offers a competitive advantage by focusing purely on internal reactions
“If I was to sort of sum up the central maxim there, it would be, you don't control the world around you control how you control your thoughts, you control how you respond to the world around you, and so the Stoics are Focused exclusively on that stuff, and tha…”
Assertion Not checkable as stated
Tony Robbins offered Holiday double his rate for a million-copy bestseller
“Tony Robbins called me and wanted me to work on his book for, like, double the amount, and that book has sold, like, a million copies since.”
Opinion
Robert Greene spends 80 percent of his working time on research
“I would say probably 80% of his work is in the research, and 20% is in the writing.”
Assertion Supported
Holiday: Historical records show Marcus Aurelius cried but never lost his temper
“We have a couple of stories of Mark's realest crying, but we don't have any stories of him losing his temper.”
Disclosure
Holiday: Establishing the next project before finishing prevents existential angst
“There's a couple parts of my process that are integral to the output that I have, which is one, I always have the next idea set before I finish writing. The one that I'm on. So there's not this sort of, like, existential angst about, like, what I do next.”
Assertion Not checkable as stated
The most famous Stoics dominate because their written works survived completely
“The reason Seneca, Marcus Aurelius, and Epictetus are also the most famous is because their works survive the most completely. So all you really get from the other people are fragments anyway.”
What-if
Holiday credits author Robert Greene with making him a writer
“I would not be a writer if it wasn't for Robert Greene. I would not be, Able to think the way that I think if it wasn't for Robert Greene, I'd be a much worse person if I never met Robert Greene”
Ryan Holiday