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067 – Wisdom Takes Work, by Ryan Holiday

December 11, 2025 Leave a Comment

In this episode, I unpack the lessons from “Wisdom Takes Work” by Ryan Holiday.

You can watch the episode here:

Full Transcript:

The philosopher Diogenes the cynic was once confronted about something he used to believe. Quote, and there was once a day when I would piss in my bed, he said as a way of reply, but no longer. John Maynard Keynes had a good reply to the same proposition. He said, quote, when the facts change, I change my mind. What do you do, sir? That’s what the lyrics to Amazing Grace are about, after all, written as they were by an ex-slaver who had seen the evil of his ways. I once was lost, but now I’m found. Was blind, but now I see.

Sure, it would have been better to have been found earlier, to change earlier. Most people stay blind. Let’s give some credit to those who don’t. I’m Mickey Mellen This is Stacking Knowledge. That was a little bit from Ryan Holiday’s new fantastic book, Wisdom Takes Work. So let’s dig in. It starts with the part one here is about your training ground. It has a simple quote from Seneca that says, quote, simply, no man was ever wise by chance. know, people don’t become wise. You can become smart perhaps, but wisdom and knowledge are two different things. This is about wisdom. About taking that knowledge further.

And no one ever just becomes wise by chance. You don’t happen to be like, I’m wise one day. have to, it takes work to do it. And this book unpacks really the people that have done it, how they’ve done it, how you can do it. And it’s got just fantastic stuff in it. And I’m excited to kind of dig into this with you. So let’s keep going here. The next chapter he calls a most unusual education he has a quote from Marcus Aurelius that I really liked just to kind of frame life. know, he’s a big, Ryan Holiday is a big stoic guy, stoic philosopher just about, you know, living life to the fullest, but really

making sure you respond in the way that you need to respond to things and not worry about letting the world affect you too much. He has this quote from Marcus Aurelius, says, quote, imagine that you have died. Now take what’s left of your life and live it properly. I love that. Just kind of like jump way ahead in life and be sad that it’s over and say, wait, but it’s not, I’m back here today. And I’ve heard a similar thing before that said, imagine you woke up and you’re 92, you’re in bed and 92 saying, gosh, I wish I was back to whatever age you are today. And now open your eyes and you’re still here. You still have that chance.

Let’s do it. You know, love that that kind of approach there. And he says, there’s another quote in the book. He says, what can we say we know? What can we say we have learned from life in Montaigne? First, the education is something that does not end. We know that an education, even if directed by someone else in the beginning, eventually reverts into our own hands. We must teach ourselves if we are to learn anything. He talks about that a lot in the book as well, that we have people to help us educate us for the first 20, 25 years of our life. But after that, it’s up to us.

And it’s up to you. And again, this is what this book talks about is these people that became wise. They’re the ones that continue their education on their own in various ways. And we have more opportunities than anyone in history to educate ourselves for essentially nothing. You know whatever device you’re listening to on this, you have access to YouTube and podcasts and like the world’s information is right there. You can do it. And so let’s, let’s do that. next he said his chapter is called talk to the dead. talking about using again, those that have gone before us and learning from them.

The quote in the book here is he says quote, meanwhile, while Charles de Gaulle was president of France, he read two to three books a week and was famous for reading all the annual winners of literary prizes. So it talks a lot about people like Charles de Gaulle that would read a lot.

I also like this quote here I pulled from Poor Charlie’s Almanack, another fantastic book that I’ve covered before. He says in the book there, this is Charlie talking, says quote, I think you learn economics better if you make Adam Smith your friend. That sounds funny, making friends among the eminent dead. But if you go through life making friends with the eminent dead who had the right ideas, I think it’ll work better for you in life and work better in education. It’s way better than just giving the basic concepts. And so Charlie talked about that a lot and now Ryan does too, about yeah, using those that came before us that recorded their lives for us and learning from them.

Charlie Munger is a great example of that. He passed away recently at the age of 99, in the last couple of years, but he recorded his stuff. We can learn from him now. So he was learning from the dead before him. We’re learning from him and keeping it going rather than having to learn everything from scratch. His next chapter was about being curious. He talks a lot in this chapter about the Wright brothers and their curiosity. I love this little quote here. He says this section, it says, quote, it isn’t true to say we had no special advantages Orville would say after he and his brother had changed the world and taken man into the air.

The greatest thing in our favor was growing up in a family where there was always much encouragement to intellectual curiosity. We’ll talk more about them in a bit, but the Wrights were famous for the curiosity. They would spend hours on the beach at Kitty Hawk just watching the birds, trying to figure out why the wings bent certain ways. And they were kind of the first to discover among the first to discover that birds took off into the wind. You kind of think you get the wind at your back and take off that way, but just spending hours watching and say, they go into the wind to get more lift more quickly. And so just things like that helped them eventually, of course, create the first plane.

His next chapter is called Ask the Question. Quote here he says, quote, we are born full of questions. We want to know the names of things. We want to know how they work. Most of all, we want to know why, why, why. But too many people lose this impulse as they grow into adults. Quote here from Isidor Rabi says, quote, I think physicists are the Peter Pan’s of the human race. They never grow up. They keep their curiosity. And so yeah, the smartest people in this case, Isidor is saying physicists are the ones that keep asking questions. And he’ll talk about that a lot in the book too about.

Being comfortable with I don’t know and having the wrong answer, just always trying to learn and expand versus saying, yep, I’ve got it. I’m good. And just coasting through life. I talked about learning to listen. A lot of the books we cover talk about learning to listen and listening well. He has a quote here from Marcus Aurelius from his book, Meditations. Ryan’s words first here. said, this is the approach of a great listener. It is a conduit to learning. We’re not just talking about nodding your head along. To be a listener is not to be passive. And then the quote from Marcus Aurelius says, practice really hearing what people say.

is something Marcus Aurelius wrote to himself. You know, he’s reminding himself to practice really hearing what people say and really hearing is tough. And we’ve talked about this before. Something I continue to struggle with is listening versus being prepared to respond. And it’s two different things. know, when you’re listening along, you want to kind of have your response ready, but you’re not listening as well. Then it’s a tough thing. He has another chapter about creating a second brain. This book really has a lot of short chapters. There’s a few long ones we’ll get into, but most of them are like six minute reads, just, you know, dozens of chapters. Fantastic. I really liked the way he approached it, but this one about

Creating a second brain, is something I’ve tried to do, just a digital notebook essentially, mine’s in Obsidian, but there are 2,700 other tools you could use to do this, whatever you’re comfortable with. in the book he says, quote, invariably at some point in our lives, we will have seen or read or heard something that would be of use to us in this situation, but will we remember it? Will we have access to it? And so I think, yeah, can we have access to the world’s information? But if you’re trying to remember that one thing you saw, Googling it or asking chat GPT is gonna be a tough challenge. But if you have your own system, you can search through.

It can help quite a bit. that’s, you’ll kind of see me do this in these books, even in these, in these podcasts where I’ll pull in quotes from other books. I mentioned Charlie Munger’s thing that I’d read before. I kind of pulled that into this situation, not as helpful as what he’s talking about. If you can pull those into situations in your life, it can be fantastic. And a second brain of some sort will help that. His next chapter is called, find your classroom. It says, quote, because an education is not something you get, it’s something you take. It’s something you make.

And so yeah, we all say you get an education, but there’s a lot of people that go through school that get an education, but don’t actually take it. They don’t, they don’t use it. So you should take and make the education you have. He talks about finding your teacher, about how it’s going to be slow, slow to learn. Well, it’s an interesting story here, from samurai warrior. I’ll kind of share this quick story from the book. He says there’s a story about a samurai warrior named Bonzo who sought an education in a hurry so he could impress his father told by a great teacher that mastery would take 10 years. He was aghast.

I can’t wait that long. What if I work extra hard? Okay, the master said, 30 years, but I will do whatever it takes to make it go faster, Bonzo pleaded. In that case, the master said it should take 70 years. A student in a hurry learns the slowest. And that’s something I’ve tried to work on as well. I’ve mentioned before that I’m reading fewer and fewer books now, still reading a lot as much as I ever have, I think, but reading fewer because I’m trying to go slower. I’m trying to learn more, absorb more, do things like this podcast, take lots of notes.

I generally listen at 1.0 X. I don’t speed it up. I want to take my time through it. I can reread things and highlight and just, yeah, making it go slower to learn more. You know, know other folks, heck, I know some folks that read a lot more books than me seem to capture all of it, which is fantastic. But for me, I need to slow it down to make it work. And that’s worked well for me. He has another chapter here called study the past. A lot of this is about studying the past. Awesome quotes from that one though. says, quote, to be useful in battle, military knowledge like discipline must be subconscious.

The memorizing of concrete examples is futile for battle for in battle. The mind does not work well enough to make the memory trustworthy. The officer must be so soaked in military lore that he does the military thing automatically. I’ve talked about this in other books too, where that’s what great athletes do too. If you’re a professional athlete, they’re not thinking what should I do in this situation? They’re thinking it before it happens. So when it happens, they can just respond automatically. And that’s what great military people do. And that’s what, you know, that wise people do to an extent.

The quote from Aldous Huxley says, quote, that men do not learn very much from the lessons of history is the most important of the lessons that history has to teach us. That men do not learn very much from the lessons of history is the most important of the lessons of history has to teach us. So yeah, basically learning that others aren’t learning from it is a thing you should learn and try to correct that. And then they talk about this chapter called studying the past, but he shares in here, it’s not really about the past. says, quote, history you must understand is not about the past. It’s a lens for understanding the present.

And that’s why we fight over what gets taught. It’s a way of predicting, even determining the future. Part two of the book, the sirens, the perilous rocks you must be aware. So just things to be nervous about. He has a very, very long chapter in here about Elon Musk, and he’s not a big fan of Elon Musk. He appreciates the great things he’s done, but is disappointed to see where he’s gone and kind of fallen off a little bit. I’ll share a little bit about that stuff. You can read quite a bit in the book there. But there’s certainly some good things that Elon had here. So this one, I don’t this is a good or bad, kind of in between.

I’ll read this quote here. says, quote, it was partly these experiences that led Elon Musk to articulate the idea he came to call the idiot index. The difference between the quoted price of something, a rocket or battery or a contract to build a new facility minus the cost of the raw materials is the idiot index. The bigger the index, the bigger the chances that waste inefficiency or outright stupidity is involved. So he noticed that with parts for rockets, like he’d need this simple part. It would be tens of thousands of dollars. But it’s like $50 worth of steel. How is it that much?

And so he’d find faster ways to fashion things and machine things and it made a big difference. He also says in this chapter, he says, quote, wisdom is not work you do once it’s work you must continue to do. The mind battles against itself, against its prejudices, its simplifications, its conceits, its patterns as demons. Wisdom is not work you do once it’s work you must continue to do. And that’s kind of the whole point of this book here too. He has this section about emptying the cup, kind of like allowing your brain to take in more. Quote here, says,

because the cup does not have to be full to cause problems. A quote here from Roman poet Horace back in the first century BC, if this vessel is not clean, then whatever you pour in goes sour. And so again, if you have, if you’re not fixing the thoughts you have now, getting new things can make a mess. And the part of the reason for this, says here, quote, we alone among all species have been given a powerful mind and the gift of reason, but how do we use it? To make up reasons for what we already want to do. And so we see this a lot where,

You decide to do something emotionally and so you put logic behind it. We see that with purchase decisions, you want to buy a car because that car makes you feel good. And then you back and say, well, it has good gas mileage and it’s, you make up reasons to, for that after you already do it. Or if you’re researching something politically or whatever you say, all right, here’s what I believe. And I’m to go find things to back up my evidence versus opening your mind, emptying your cup and actually, you know, searching for what you want to do.

The next chapter he calls Write to Think Right. So W-R-I-T-E to think R-I-G-H-T, Write to Think Right. He says, his books, letters, and notepads, Thomas Merton was not telling people what he thought. He was figuring out what he thought. He was meditating on the page, sharing generously and courageously his thoughts with the world. So yeah, Thomas Merton was not telling people what he thought. He was figuring out what he thought. Reminds me of a quote from Blair Enns I’ve talked about Blair Enns a lot on here and in my blog and stuff.

He runs the Two Bobs podcast, has a book called Wind Without Pitching, a lot of great stuff from Blair. But Blair says, quote, I think through my fingers. I have to write to fully understand and derive some sort of cohesive point of view on it. And that’s precisely why I blog so much. I’m thinking through my fingers. know, most of my posts are just forcing me to unpack my ideas and figure out if they’re right or wrong and back up or, you know, kind of go through that. So I love that. Write to think right. His next chapter is called Assemble Your Board of Directors. He says, quote, each of us needs to cultivate this approach to our own problems in our lives.

businesses and leadership positions. It’s one thing to have a mentor. It’s also important to have a scene, but at the highest levels, we must develop a board of directors that advises and consults that at times checks and even corrects us. So he talks about the benefits of a board of directors, talks about good and bad and others. He says, really a board of director, says, you know, that at times checks and even corrects us. And a good board of directors will push back on you. You know, you make the final decision, but they should push back. And it’s something we try to do with our agency too, with our clients. say,

We’re going to push back if you have bad decisions. You’re in charge, it’s your project, but we’re gonna push back. And that’s what you want from a board. Again, his dislike for Elon Musk starts showing more here. He says, quote, Elon Musk’s boards, like far too many corporate boards, are famous for rubber stamping whatever he asks, even when those requests have been unethical, reckless, or self-interested. So yeah, there’s a lot of boards out there that have a charismatic, you

powerful leader that will just let people go and make their life miserable. So they say, yes, sir. To whatever, even when those requests have been unethical, reckless, or self-interested. the other idea here, he didn’t get into too much. It was creating a virtual board of directors. I’ve seen this before and ideas where you kind of have a virtual board of directors kind of think through what they might think of your idea. I’ve done that before, like with our business coach. like, I need to reach out to him with this question, but I’ll stop and say, okay, what would he say? Okay. If I’ve responded to that and I kind of worked through the conversation first, it makes me sharpen my thoughts and

have a better question leading with the already into the conversation. So you can do it with a virtual board of directors. have mine. I’ve not used as much lately. I need to. It’s a good thinking exercise, but people like Seth Godin, Charlie Munger, Blair Enns mentioned a minute ago, Gary Vaynerchuk just, if I come up with an idea and bring it to Seth Godin, what would he say about it? You know, I have listened to all these folks enough. I have a good idea of what he might say and say, Oh gosh, well, how would I push back against that? And I kind of get a lot done that way. Further, I’ve seen people using AI for this, you know,

AI is very familiar with Seth Godin and Charlie Munger and Elon Musk and Ryan Holiday and all these things. can say, I have this board of directors with these people. Remember this. Now let’s ask them questions. What would this group have to say back? And it can be interesting what it says. Like a lot of AI, it may be wrong too, but at least it’ll get you thinking. Say, oh, I wonder if Ryan Holiday would have that angle on this idea I have. What would he think of it there? It can make you go a little bit different. The next chapter he calls, Don’t Be a Know-It-All. He has another quote here from Epitetus. He says, remember,

Epictetus told his students many of whom were not gifted and bright but the sons and daughters of the most powerful families in Rome. It is impossible to learn that what you think you already know. This is something I’ve shared before. This comes up in books a lot. It is impossible to learn that what you think you already know. If you’re sure you have the answer, then you’re not going to learn and if you’re wrong, you’re never going to find out. So yeah, he says don’t be a know it all. Talks about a little bit. It’s partly don’t be a know it all so you can learn more, but also don’t be know it all because it’s kind of a jerk. I love this quote from Dave Barry. I’m not sure where it came from the comedian Dave Barry. says quote,

I can win any argument. People know this and steer clear of me at parties. Often as a sign of their great respect, they don’t even invite me at all.” I love that. He’s just saying, I’m a know it all and people are jerks know, or people think, no, I’m a jerk. So yeah, just be careful of that. But I think the point Holiday is making is not the jerk side of it as much, but the, you think you know everything, then you’re done. You’re not going to learn anything else. And that’s problematic. He gets into a lot of watching your information diet. I think Holiday is good about this as a person, as most anyone else, just the way he

consumes information from books and is careful with social media and all that stuff. He has another chunk of the book where he goes after Donald Trump pretty hard for his learning habits, which I think is pretty fair here. So talking about the security summaries Trump gets, it’s a longer quote here. I’ll just read this here. says, quote, he touched it. Trump’s first CIA briefer said when he asked if Donald Trump had read his briefing, he doesn’t really read anything.

Instead, Trump tended to skim the document, itself a summary of insights that were often written with the sweat or blood of intelligence operators and informants secured through great expenditure, his attention only occasionally piqued by graphics and pictures. He liked bullet points. He talked more than he listened so that, according to one observer, there might be eight or nine minutes of real intelligence in an hour’s discussion. And even this expert opinion has to battle it out with whoever Trump talked to last. The president, as one advisor put it, will ask 49 people for their opinion and stop at the 50th if he likes the answer.

A fool only hears what they want to hear. He also says here, go straight to the source when you can and check sources always, you know. So a fool only hears what they want to hear. Again, goes back to, mentioned a minute ago, if you have an idea politically or whatever about something you want to see, you will go find evidence for it. There’s evidence on the internet to back up any ridiculous claim. If you think the earth is flat, you will go find a couple of hundred people out there that have videos that back you up. They, yep, the earth is flat. know, fool only hears what they want to see and then go straight to the source when you can check sources always. And this is

bigger problem on social media I’ve talked about before lately where social media really discounts links so much that people don’t include links with things. So instead of having a conversation about the source of an article or a statement or whatever, you just get a screenshot of whatever people want to say and the comments become around that. People aren’t willing to go to the source because it’s one extra click away to go find it. So yeah, check sources always. Next in the book here, he says, change your mind. He has a lot about changing your mind here. So let’s dig into some of this.

Let’s see, where do I want to start? We’ll go with, yeah, the philosopher, Diogenes again.

So in this section is the part I said at the beginning with the quotes from Diogenes and John Maynard Keynes and the lyrics to Amazing Grace. You know, I’m not gonna read that whole quote again, again, the end it said, sure, it would have been better to have been found earlier to change earlier. Most people stay blind. Let’s give some credit to those who don’t. So.

Again, I once was lost, but now I’m found, was blind, but now I see. Would have been better to have found it earlier, to change earlier, but hey, give credit to people who actually make changes whenever it might be. And then he also says in this chapter, says, the real failure, however, is to have never changed. Imagine still believing all the things you believed as a kid. Imagine still believing in and acting the same way you did before something happened. When someone calls you stubborn, it’s not a compliment. A fool stays the same. So yeah, be willing to change. Another chapter here, so we’re kind of getting toward the end a little bit.

He says, don’t be a snowflake. He says, once you have been disabused of your notions about something or the paucity of your knowledge about something, you’re not free at all. Now you have to go learn. Now you have to change your mind. Now you have to admit you were wrong. Now you have to go do some real work. As you become successful, it becomes easier and easier to become cocooned in your own comfortable certainty. This is also one of the downsides of finding your people. You may well surround yourself with people who think like you do, who act like you do.

All the while your intellectual immune system is growing weaker and weaker because it’s no longer being exposed to new and interesting ideas. Again, I think this is another problem social media has brought on us. It wants to show you the things that you want to hear so you stay on longer. you know, any Republican that goes on social media thinks, gosh, the whole world is all Republican. Any Democrat that goes on social media says, wow, the whole world’s all Democrats. Like you don’t see the opposing views as much unless you go out and search for them specifically. He says snowflakes make bad decisions because every decision is decided by the least consequential variable.

Does this align with what I want to be true? And so yeah, they kind of say, does this align with what I want to happen? Yes, cool, I’ll accept it. If not, then they’re wrong or crazy. They’re, whatever they want to be. His next chapter here is called seek criticism. He says, quote, criticism may not be agreeable. Winston Churchill once said, but it is necessary if it feels the same function as pain in the human body, it caused attention to the development of an unhealthy state of things. So yeah, Churchill was famous for having people around him that would criticize him. He wanted the criticism to, to,

Again, call attention to the development of an unhealthy state of things to make sure he knew where he was wrong. And again, he would push back when needed, but he would also listen when needed. He has a chapter called Make Mistakes, which again kind of transverses the book too, he says, quote, wisdom is not only making mistakes and learning from them, it’s also not being ashamed of having made them. In fact, we talk about our mistakes openly so we can codify the lessons for ourselves, not codify lessons, not just for ourselves, but for others.

Yeah, wisdom is not only making mistakes and learning from it. It’s also about not being ashamed of having made them. If people get shy about making mistakes, try to hide it. They still may learn some if they actually saw the mistake. But man, if you can share your mistake for others and we can all learn from it, that can be fantastic.

his next chapter, a few chapters up, I guess is don’t fall for it. Just being careful. The quote here he says we should absolutely quote, do our research to borrow the term popular with conspiracy theorists. But by that we mean actually do the research, like read real and credible authors on a topic. Lots of them do actual thinking, not just what feels like thinking, ask real questions instead of quote, just asking questions, listen to the answers, allow ourselves to be proven wrong.

allow ourselves to learn new things. A podcast is not a sufficient briefing on a topic. And so yeah, you’re listening to this podcast, you you need to go further on anything you hear here. You may agree with some of it, like some of it, want to learn more, like go learn it for yourself, then go dig in, go read more, ask questions. know, a podcast is not a sufficient briefing on a topic. And again, a lot of people will listen to a podcast or watch a video and say they’ve done their research and that’s really not research. You know, do actual thinking, not what feels like thinking, ask questions, you know, really dig in and don’t just fall for, you know.

the quick things you hear. He talks about going from humility to wisdom. He says, quote, being wrong is not the sin. Being confidently wrong, that’s the problem. That’s the difference between ignorance and stupidity. And so being ignorant is okay. He’ll talk about it. If you’re ignorant on something, that’s okay. You can fill that gap. If you’re stupid, that’s where you’re being confidently wrong. You’re saying you’re confident in what you believe and it’s not correct. And so.

Yeah, being open to not being correct is very valuable and understanding where things can always change. Next part of the book, he gets a lot into Abraham Lincoln. And I learned a lot about Lincoln just from this book. I’ve not read Lincoln a ton over the years. And so I thought it was very interesting here. So we’ll start here. said, Lincoln eagerly chose Edwin Stanton, the Democrat who once called him the original gorilla and tried to get him fired from an important legal case in 1855.

He said that Stanton was the perfect secretary of war. And that’s all that Lincoln cared about. He had no right. Lincoln believed to deprive the country of the best and most able operators just because they had hurt his feelings or disagreed with him on many issues. So Lincoln famously hired people when he was president to work under him that he had run against and who had been, you know, they disagreed a lot in the past, but that’s what he wanted. He said, I disagreed with him, but he’s a smart dude. want smart people here. I don’t want to just have people that just are yes men for me. I want to really do the best things for the country. You know, he said,

He had no right to deprive the country of the best and most able operators. He also says in this chapter here, Holiday does, says, quote, wisdom is not erratic. It is not impulsive or emotional. It is calm. It’s cool. It’s patient. It’s kind. It’s philosophical. And so yeah, wisdom is focused. You don’t see wise people aren’t just going haywire. They’re focused, they’re calm, they’re cool. And that’s kind what we talk about here. The next chapter is practicing empathy. He talks more about Lincoln here. He says, perhaps Lincoln’s greatest skill was his empathy. He detested slavery.

Nearly his entire political career was based on his resistance to the expansion of the slave powers that had captured the country and betrayed the fundamental principles that it had been founded on. And yet he seemed to perfectly understand why slave owners thought and acted the way they did. And that’s empathy in a nutshell there. Like he doesn’t agree with them, but he understands why they did. If he just says you’re wrong and they fight, they’ll just fight. But if he understands, okay, here’s why they have it. They need the help. They need the money. Like he doesn’t agree with them at all, but understanding their side of it is important.

Holiday kind of sums it up in this part of the chapter saying quote this empathy didn’t mean he accepted their logic or forgave their crimes for he also thought long and hard about what it must be like to be owned by another person to have your labor stolen from you only because of your skin color so while he had the empathy to understand why slave owners might do what they did He also had empathy for what it would be like to be a slave and that’s why again He detested slavery in his entire career is based on resistance to the expansion of it This chapter reminded me a lot of the book. I never thought of it that way

Monica Guzman wrote, she talks a lot about their like understanding doesn’t equal agreement. You know, I never thought of it that way. It’s all about understanding how people think, why they think that way, what’s driving them to think that way. Not necessarily agreeing, but just understanding it like, I didn’t realize that’s why you might vote that way or believe this thing or buy from that company or whatever, whatever it is you do. If you at least understand, I never thought of it that way. I understand now why you did don’t necessarily agree with them, but now it can make the conversations much more fruitful. The next chapter here is called Be Humble.

He says, fools are rarely humble, but brilliant people often are. It’s not that you’re always wrong, but you understand you always could be. It’s the irony of wisdom that the smarter you get, the less you need to feel like a smart person, the less you need to be right. The more comfortable you are with uncertainty and ambiguity and of course humility. And so yeah, yeah, it’s not that you’re always wrong. you know, smart people, brilliant people are not always wrong clearly, but they understand they always could be. There’s nothing that’s, that’s certain. They always realize there’s, there could be something I’m missing and I’m open to understanding it.

next chapter is called Always Stay a Student. Again, talking about Abraham Lincoln here. He says this is a longer quote. I’m going to read this whole little story to this. I thought it was a great piece here. He says, the most critical case of Lincoln’s life was actually one where he was basically fired. Lincoln had been hired by McCormick Reaper for his patent expertise and local standing, but he was quickly outranked and outshined by other lawyers, including Edwin Stanton, his future secretary of war. We talked about him a minute ago.

Bumped from the case, Lincoln was told he could go home and be paid anyway. Still, Lincoln decided to stay and observe the trial, even though he was allowed to make no arguments and was deliberately ignored by the other lawyers, who refused to even speak to him, let alone inform him of developments on the case. It could have been humiliating for a former congressman, but Lincoln never complained. He just showed up and watched. At the end, he told a friend that he was going home to, quote, study the law. You stand at the head of the bar in Illinois now, his friend said in surprise. What are you talking about?

I do occupy a good position, Lincoln admitted, and I think I can get along with the way things are going there now. But these college-trained men who have devoted their whole lives to study are coming west, don’t you see? They study in a single case, perhaps for months, as we never do. I’m as good as any of them, and when they get out to Illinois, I will be ready for them.” So Lincoln, yeah, was already a former congressman, was a well-known lawyer, and they said, hey, we don’t need you on this case. You can go home. And he stayed, didn’t need to, essentially wasn’t getting paid for it, because he was getting paid either way, so he was giving his time for free at that point. But stayed just to learn, because, he…

He knows there’s more coming and Again, the chapter is always stay a student and Lincoln was fantastic about that. Jumping ahead a bit, he has a chapter called Be Happy. He says, remember, the basis of Stoicism is focusing on what you control. Happiness that is dependent on things outside your control is a recipe for unhappiness. Happiness that is dependent on things outside your control is a recipe for unhappiness. So if you can only be happy based on other things happening, you’re in big trouble. But if you can focus on what you control and stay happy regardless, you’re gonna do well.

He has a chapter called Suffer into Truth. I won’t get too much into this one, but he talks about Charles Darwin and Katalin Kariko says, Charles Darwin, course, origin of the species, Katalin Kariko developed mRNA research that helped with COVID vaccines. He says, quote, two decades passed between Charles Darwin’s Voyage on The Beagle and the publication of On the Origin of Species. And while this period was hardly a prison sentence, it was an exhausting ordeal for him. The same went for Katalin Kariko, who toiled away in the bowels of academia as she developed her groundbreaking mRNA research.

So Kariko I believe, started studying this like in the 90s and had failure after failure after failure and took 30 years for this research to work. So he says, yeah, suffer into truth. Darwin did the same where he was decades before he was able to figure out what he needed there. People don’t just become wise and brilliant overnight. They have to dig into it. And these are two that made profound impacts on the world. And it took him years and years to get there.

He has another chapter called Don’t Lose the Wonder about just staying open to what the world has around us. I’m not gonna actually read from his book. I’m gonna pull a bit from Mark Richt, former college football coach. had a book called Make the Call, talk about being weary of wonders. I like this quote from his book. So I’m gonna jump over there for a sec. He said, from Richt’s book, he said, So I kind of like how author GK Chesterton said it. A British writer of the 20th century. He talked to how we become, quote, weary of wonders.

Like how if we were to see the sun for the first time, we would think it’s the most incredible thing ever. But because we see it every day, because we’ve seen it hundreds and thousands of times, we don’t even look out the window for it in the morning. We don’t even think about it. The sun’s up again, big deal. And so as Richt talks about in that book and of course, Holiday talked about here is like, yeah, stay wondrous, stay enchanted by these things. He gives lots of examples of this chapter of people that do that. Again, well worth reading. Next chapter, he calls grasp the essence.

Really like this first quote again jumping back to Lincoln again. There was a lot of a lot of Lincoln stuff in the second half of this book so This is regarding Abraham Lincoln here He says quote that was his frustration with general George Meade in the aftermath of the great victory at Gettysburg Meade had wired that he repelled Lee from Maryland and thus driven the enemy from our soil Lincoln was stupefied. Will our generals never get that idea out of their heads? said in frustration that the whole country is our soil

So again, Lincoln obviously wanted to win the war, but it was for the benefit of the entire country. Whereas Meade is like, hey, we stopped those dang southerners and kept them off our soil. Lincoln’s like, no, no, it’s all of our soil. And so again, I love leaders that do that. There’s some leaders that do that, that want to unite the country, even if they disagree with some and some that want to rub the other half out, which is not great. Another piece in here in this grasp the essence chapter, he says, quote, the purpose of wisdom is not to be able to hold an enormous catalog of facts in your head, it’s to be able to distill those facts to decipher what they mean.

to get to the essence of an issue, a problem or a story, to see the here and now, the only thing that accounts. And so again, wisdom and knowledge are two different things. Knowledge is kind of a prerequisite for wisdom in a lot of ways, but it’s not nearly enough. If you have all these facts in your head that doesn’t help. Wisdom requires you to distill them out. He has another chapter called, Pass the Final Test, essentially dying with dignity. I like this quote he shared from Seneca in here. says, but what of the sadness that death leaves behind?

Seneca, who had buried a child and many friends had written some of his best work on grief. Who would want their memory to torture their friends and loved ones after they were gone? We want them to think of us and smile. We want them to think of us and do good. I leave you my example, he says to his friends as my gift. And so, yeah, I like that approach from Seneca. Like we don’t want people to cry for us when we’re gone. We want them to smile and think of us. We want to think of, think of us and go do good things, you know? So that’s an interesting way to phrase things, to put it and that chapter, digs into that quite a bit more there too.

The last regular chapter in the book, we’ll do a little bit from the afterword as well, the last regular chapter is called wisdom is virtue, virtue is wisdom. There’s two quotes in here I’m gonna share. The first quote, the four virtues, he talks about the four virtues, wisdom being the fourth, he has a fourth book in a four part series that Holiday’s written. It says the four virtues of our instilling character, good character, so that at the critical point, a person’s true nature kicks in. Wisdom is not something that just happens to you and no one was born with it.

But the good news is that once you learn something, as the great John Lewis’s mother used to tell her son, no one can take it away from you. It’s ours forever if we choose to use it. And once you learn something, no one can take it away from you. It’s yours forever. And so yeah, that’s where wisdom can become virtue. And then he has a quote here. He says, quote, whether it’s from the Bible or from Hercules or East of Eden or Faust, the parable’s message is the same. We have a choice. We choose between wisdom and ignorance, cowardice and courage, discipline and excess.

right and wrong, virtue and vice. You have a choice in all these things and yeah, you get to make the choice to do what you want to do. And then just a little bit from the afterward to kind of wrap this up. Wisdom Takes Work from Ryan Holiday, just a fantastic book. Totally encourage you to go check it out. the last thing I’ll leave you with is here. says, one thing I’ve noticed, I’m calmer, I’m quieter, I argue less, I get upset less. I admit I am wrong more often. This is wisdom, Epictetus said, getting in fewer fights, letting more things go, focusing more on what you control.

a smooth flow of life.

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Warren Buffett reads over 400 books a year. Bill Gates takes an annual two-week vacation that is focused on reading. Mark Cuban reads more than three hours almost every day. There is no doubt that learning from others is a fantastic way to improve yourself.

That said, there are tens of thousands of business books published every year, and it’s impossible to keep up. You read what you can, we’ll share what we can on here, and we’ll all get better in the process.

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