The Ledger

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Insight
Holiday: Singular domain excellence creates inherent psychological imbalance
“There is something inherently unbalanced about Excellence in a singular domain, because you are focusing all of your energy on one thing. There's something dysmorphic about like the athlete's physique. And that's probably just the physical manifestation of als…”
Ryan Holiday Nov 26, 2024 ▶ 32:25 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Cancel culture pushes disgraced public figures into radicalized caricatures
“And what would happen today is that this person would be basically shoved by one half of society, and then perversely, like, embraced by another darker side of society that Doesn't like those people, right? And you would see him get radicalized and fight again…”
Ryan Holiday Nov 26, 2024 ▶ 1:12:51 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Delaying decisions costs more than making the wrong choice
“Whatever the margin of error would be between one decision or the other is far smaller than whatever the opportunity costs of not having it done. And moved on to the next thing are.”
Ryan Holiday Jan 11, 2022 ▶ 39:48 #128 Ryan Holiday: A Stoic Life
Insight
Holiday: Idealists fail because preoccupation with ideals clashes with reality
“I think the problem with a lot of idealistic people, particularly people who are interested in social change or social justice, is that they're, This preoccupation with how they want things to be puts them at odds with how they are and actually makes it much l…”
Ryan Holiday Jan 11, 2022 ▶ 43:44 #128 Ryan Holiday: A Stoic Life
Insight
Manual transcription creates a vital physical ritual for processing research notes
“The idea of just quickly being able to copy and paste stuff is antithetical to what I'm doing and why, like, it's the ritual that's important, and the act of taking it longhand is very important. Obviously, if it's like a, you know, huge paragraph, I'm gonna t…”
Ryan Holiday May 16, 2016 ▶ 24:53 #11 Ryan Holiday: The Stoic Whisperer
Insight
Writing non-fiction without a discrete target and outline is highly dangerous
“What you don't do, what I think is the most dangerous thing for writers to do, is to just, and maybe it works when you're writing fiction, I don't know, but sitting down and just writing. Like, you can't hit a target that you didn't aim for.”
Ryan Holiday May 16, 2016 ▶ 30:02 #11 Ryan Holiday: The Stoic Whisperer
Insight
Consultants should charge for strategic thinking instead of pitching for free
“People think, like, the execution is the hard part, but to me, the thinking is the hard part, so I'm not going to think for free and then get paid to execute. I would rather get paid to think and then maybe get paid a little bit more to execute, or if you want…”
Ryan Holiday May 16, 2016 ▶ 40:31 #11 Ryan Holiday: The Stoic Whisperer
Insight
Holiday: Succeeding by ignoring critics creates a dangerous anti-feedback mindset
“Often to be successful as an entrepreneur, you get there by not listening. You get there by not listening to the odds, not listening to the doubts, not listening to the critics, and then You succeed. So then you get this very wicked learning environment where …”
Ryan Holiday Nov 26, 2024 ▶ 2:37 Ryan Holiday: How to Win the War with Yourself
Insight
Ryan Holiday: Dissecting past blame distracts from choosing immediate action
“How I got here is separate and independent from the fact that I currently am here. I might need to, at some point, examine those causes so I can learn from it, but my impulse to dissect And blame and question what has happened is actually just a really conveni…”
Ryan Holiday Nov 26, 2024 ▶ 9:39 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Journaling is to Stoicism what meditation is to Buddhism
“Journaling is to stoicism as meditation is to Buddhism. It is the practice of having a conversation with yourself about your thoughts, and beliefs, and values, and actions”
Ryan Holiday Nov 26, 2024 ▶ 10:48 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Framing interpretations as personal stories invites clarification instead of conflict
“By you saying what I make up about that is, or the story I tell myself about that is, Or the way that sounds to me is you are not expressing your interpretation of reality as reality. And therefore you are offering the person the opportunity to correct or upda…”
Ryan Holiday Nov 26, 2024 ▶ 15:35 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Stoicism teaches processing emotions rather than suppressing them
“And so I think, to me, Stoicism is a set of exercises and insights and practices to help you understand those emotions, process those emotions, and not be ruled by those emotions.”
Ryan Holiday Nov 26, 2024 ▶ 17:15 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Stoic joy is resilient flourishing amidst adversity, not superficial cheerfulness
“And I think when the Stokes thought about joy and happiness, they were thinking about a more resilient form of that emotion, not Fun smiling, cheerfulness, happiness, but like a happiness of a person who is surviving the blows of fate and flourishing as a huma…”
Ryan Holiday Nov 26, 2024 ▶ 22:47 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Retiring at one's peak takes more discipline than chasing more titles
“It clearly takes more discipline to walk away early or on top than it does to go for the sixth ring or the three-peat or whatever. Those things are extraordinarily hard, but clearly if Less people do this other feat. It must be because it's even harder.”
Ryan Holiday Nov 26, 2024 ▶ 37:54 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Childhood perceptions of money persist even as income grows
“Kind of like what seems like a lot of money to you as a kid always remains a lot of money to you, even as your income goes up.”
Ryan Holiday Nov 26, 2024 ▶ 46:04 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Compulsive overwork produces temporary relief, not genuine accomplishment
“I think that's the thing about most compulsive tendencies is they're not based on anything. You have this belief that if you don't do it, things will fall apart. It's not based on anything real. And most of the time what you get is not even the reward for doin…”
Ryan Holiday Nov 26, 2024 ▶ 1:00:01 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Workaholism is uniquely dangerous because society validates and rewards it
“It's somewhat productive, and it's socially adaptive. Doing heroin, or, you know drinking all night tends not to have positive social reinforcement, but being really good at what you do, and Thriving on that feeling of being validated for being good at what yo…”
Ryan Holiday Nov 26, 2024 ▶ 1:01:14 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Ignorance of peers' actions leads to healthier direction and focus
“And so I think the more indifferent and probably ignorant you are of what your peers are doing, the healthier you are and the Cleater your compass reading will be.”
Ryan Holiday Nov 26, 2024 ▶ 1:02:58 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Virtue is a practice built through repeated actions, not a fixed trait
“Wouldn't it be far better to think of virtue as a verb? Aristotle says, like, how do you get better at playing the flute? It's by playing the flute. How do you become a more generous person? It's by doing more generous actions.”
Ryan Holiday Nov 26, 2024 ▶ 1:10:04 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Modern work structures are incompatible with societal expectations of active parenting
“We're expecting rightfully so for parents to spend a lot of time with their children, but the world is not conducive to that at all, unless you've retired or you're not working.”
Ryan Holiday Nov 26, 2024 ▶ 1:22:00 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Predictive AI Consistently Fails to Anticipate Sentences by Master Writers
“Never is the AI able to predict the next couple words in that sentence. I've always found that very interesting. And it's a reminder to me that still the act of creative genius of doing Not any sentence, but like the right sentence, the right way with the righ…”
Ryan Holiday Nov 26, 2024 ▶ 1:33:23 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Success is seeing your kids; power is controlling your schedule
“Like I've been saying recently, like success is how much you see your kids and power is how much control you have over your schedule.”
Ryan Holiday Nov 26, 2024 ▶ 1:38:19 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Jealousy Requires Trading Your Entire Life for Someone Else's
“When I feel jealousy, I try to remind myself that you can't pick and choose. Like if you want what someone has, You have to trade your whole life.”
Ryan Holiday Nov 26, 2024 ▶ 1:40:51 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Straddling Two Different Strategies Will Destroy You
“Strategy is by definition choosing certain objectives and not choosing other objectives, and if you try to straddle two strategies, you'll destroy yourself.”
Ryan Holiday Nov 26, 2024 ▶ 1:42:13 Ryan Holiday: How to Win the War with Yourself
Insight
Holiday: Most personal and historical mistakes stem from primal emotional passions
“I would say 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…”
Ryan Holiday Jul 4, 2023 ▶ 4:43 TKP Insights: Philosophy
Insight
Holiday: Success ironically brings higher-paying distractions that threaten focus
“The irony of success is that there are infinitely more distractions from that success. And as you get more successful, the higher the price or bribe attached to those things is, right?”
Ryan Holiday Jan 11, 2022 ▶ 9:51 #128 Ryan Holiday: A Stoic Life
Insight
Holiday: Small quality drops from overcommitting compound until career opportunities disappear
“So let's say I'm continually saying yes to a bunch of stuff on the first book. There's a five percent, you know, decrease in quality. And then the next book, there's a 10% decrease in quality. And the next one, there's a 15%. Now I've significantly fallen off.…”
Ryan Holiday Jan 11, 2022 ▶ 12:08 #128 Ryan Holiday: A Stoic Life
Insight
Holiday: Comparing creative success to peers is a recipe for misery
“To judge your success, Comparative to other people in this profession is just a recipe for complete misery.”
Ryan Holiday Jan 11, 2022 ▶ 15:19 #128 Ryan Holiday: A Stoic Life
Insight
Holiday: Critical reception and creative quality are decoupled from book sales
“You can write your best book, and it could sell the fewest amount of copies. You could get the most critical reception, and it could, ah, it could sell the fewest amount of copies. All you should really focus on is like, are you proud of it? Did you do what yo…”
Ryan Holiday Jan 11, 2022 ▶ 16:24 #128 Ryan Holiday: A Stoic Life
Insight
Holiday: Insatiability is the key differentiator in high performers
“Inherently, the insatiability is the key differentiator in a lot of high performers, and I think there's a Stefan Zweig quote where he says, like, never before has a conqueror been surfeited by conquest, meaning, like, no conqueror was ever like, I won, and no…”
Ryan Holiday Jan 11, 2022 ▶ 26:08 #128 Ryan Holiday: A Stoic Life
Insight
Holiday: Sustaining elite performance requires systems and routines over willpower
“If, and you almost certainly can't just do it on raw willpower or talent alone anymore. It requires a team. It requires an environment. It requires a routine. You know, it requires all those things.”
Ryan Holiday Jan 11, 2022 ▶ 33:18 #128 Ryan Holiday: A Stoic Life
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.”
Ryan Holiday Jan 11, 2022 ▶ 38:42 #128 Ryan Holiday: A Stoic Life
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…”
Ryan Holiday Jan 11, 2022 ▶ 49:33 #128 Ryan Holiday: A Stoic Life
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.”
Ryan Holiday Jan 11, 2022 ▶ 1:07:02 #128 Ryan Holiday: A Stoic Life
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…”
Ryan Holiday Jan 11, 2022 ▶ 1:07:44 #128 Ryan Holiday: A Stoic Life
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.”
Ryan Holiday Nov 26, 2024 ▶ 18:59 Ryan Holiday: How to Win the War with Yourself
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.”
Ryan Holiday Nov 26, 2024 ▶ 25:49 Ryan Holiday: How to Win the War with Yourself
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.”
Ryan Holiday Nov 26, 2024 ▶ 47:01 Ryan Holiday: How to Win the War with Yourself
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.”
Ryan Holiday Jul 4, 2023 ▶ 10:53 TKP Insights: Philosophy
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. …”
Ryan Holiday Jan 11, 2022 ▶ 23:19 #128 Ryan Holiday: A Stoic Life
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,”
Ryan Holiday Jan 11, 2022 ▶ 40:43 #128 Ryan Holiday: A Stoic Life
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.”
Ryan Holiday Jan 11, 2022 ▶ 55:43 #128 Ryan Holiday: A Stoic Life
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…”
Ryan Holiday May 16, 2016 ▶ 1:45 #11 Ryan Holiday: The Stoic Whisperer
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