How To Think Better in the Age of AI (From the Stoics)

The rise of social media and certainty-driven information ecosystems creates pressure against nuance, doubt, and questions because doubts and questions do not go viral, whereas certainty does; this incentive structure degradates discourse.

“And you see this on social media, too, right? There's no room for nuance. There's no room for doubt. Doubt and questions are not viral, but certainty is. And so, we have to understand that the more we learn, the more we are exposed to the things that we don't know.”

AI-generated content ('AI slop') now degrades the internet, which in turn reduces the quality of inputs available to AI systems, creating a feedback loop where AI models trained on declining-quality internet data produce increasingly poor outputs.

“And it's actually this is something they're noticing with AI, too, right? With as AI draws from what's on the internet, in some ways it can get worse from AI slop that's being put out there.”

The Gell-Mann Amnesia effect describes how when you read journalistic or scientific coverage of a domain in which you have deep expertise, you often see it is inaccurate, oversimplified, or outright incorrect; yet when reading about unfamiliar domains, you defer to the same experts or systems, forgetting they were wildly wrong about what you knew well.

“There's something in journalism known as the Gell-Mann Amnesia effect. It's named after a Nobel Prize-winning physicist. And basically, the idea is when you look at journalistic or scientific coverage of something you know a lot about, you often see how bad or inaccurate that coverage or knowledge is, right? It's simplified or it's outright incorrect, and you go, 'Whoa, these these people don't really know what they're talking about.' The problem is, we get this amnesia when it comes to coverage and knowledge about things that we're not as familiar with, right? Suddenly, we defer because those people are experts, or we defer because they seem confident in their answer.”

The ancient Stoics had a group called the Scipionic Circle, consisting of some of the wisest people in ancient Rome who gathered to debate, ask questions, and teach each other; this mirrors Benjamin Franklin's later creation of the Junto, a Philadelphia group dedicated to self-improvement.

“The ancient Stoics had this this group known as the Scipionic Circle. It was some of the wisest people in ancient Rome, and they would get together and have debates and have questions and talk about things and teach each other things. This is what Benjamin Franklin starts, his his famous Junto, which is a a group of people in Philadelphia who are dedicated to the ideas of self-improvement.”

Good thinkers do not trust their first impression; they suspend judgment, verify claims, and do not believe their eyes and ears until proven; in a world where AI can quickly provide confident answers without accountability, one must slow down, ask for sources, and demand second and third verification.

“Basically, what the Stoics want us to remember, and what all good thinkers do, is they don't trust their first impression. Don't believe their eyes and ears until they've verified, until they've proven it. They suspend judgment a little bit. So, in a world where AI can can quickly and confidently throw you answers, but it doesn't have any skin in the game as far as those answers go, you have to slow down. You have to ask it if it's sure, right? You have to get it to give you its sources.”

AI and other cutting-edge technologies make expertise in specific domains obsolete, but paradoxically make thinking itself more important because users must interpret AI outputs, craft intelligent queries, and possess the wisdom to recognize when AI is hallucinating or going in the wrong direction.

“people are talking about everything that AI is going to replace. And it is true that these technologies are going to make a lot of kinds of expertise obsolete. But, I would argue that this incredibly powerful and groundbreaking technology, what it actually does is make thinking even more important.”

Most people, even experts, do what other people do, want what other people want, and think what other people think because it is comfortable, safe, and aligned with existing inertia and energy; people do not think for themselves by default.

“Like, generally, most people, even experts, just do what other people are doing, want what other people want, think what other people are thinking. Because that's comfortable, because it's safe, because there is inertia and energy going in that direction.”

Most people consume 'straight garbage' through their information diet without the same scrutiny applied to physical nutrition, allowing poor-quality inputs to shape thinking and decision-making.

“across from the room where we were was the cafeteria, where some of the best nutritionists in the world were pouring over every calorie, every ingredient, every morsel that these guys consumed so that they could be at their physical best. I said, 'This is great, but but most of you are consuming straight garbage directly into your brain via your information diet. And we have to make sure that we're watching that diet as much as we are watching our literal diet.'”

The Stoics should be read repeatedly and continuously, not once, because rereading is fundamentally different from initial reading; even though the text remains constant, the reader changes, and each rereading reveals different insights suited to the reader's current state.

“I like to say that the Stoics aren't philosophers you've read, they should be philosophers you are reading. First off, not enough people have read the Stoics, but not enough people have reread the Stoics, right? Reading is one thing, rereading is another.”

The phrase 'You've Got Another Think Comin'' (not 'Thing Comin'') reflects the truth that first impressions and initial thoughts are often wrong due to biases and preconceived ideas, so one must be willing to reconsider initial judgments.

“You know the Judas Priest song, 'You've Got Another Thing Comin''? Actually, the expression is, 'You've Got Another Think Comin'.' It's funny because maybe they misheard it, or because we've heard the song, that's what we think the expression is. You've got another thing comin'. But for many years previous, the the colloquial expression is, 'You've Got Another Think Comin'.' Or, as we might say today, 'Think Again.' And the reason we need an expression about this is that often our first impressions, our first thoughts, are wrong, right? We have biases. We We have preconceived ideas.”

Being a good thinker is not about facts and figures or having all the right answers; small-minded people pursue complete knowledge; instead, the right question to ask is not 'what should I do?' but 'how can I be more adaptable to circumstances?'

“It's not about facts and figures, it's not about getting the right answers. No one can tell you all the things that you need to know. But this is what small-minded people are after. Epictetus tells us about a student that comes up to him and says, 'You know, tell me what to do. I want to know what to do.' And this person wanted a prescription for all the kinds of situations that they would face. And Epictetus said, 'This is absolutely the wrong question.' He says, 'You should be asking me, how can I be more adaptable to circumstances?'”

Writing is one of the most powerful ways to figure out what one thinks and what is true; it is easy to have contradictions and poorly thought-out ideas bouncing around in the mind, but sitting down and writing forces actual thinking.

“I think writing is one of the most powerful ways to figure out what you think, to figure out what is true. It is easy to have contradictions and poorly thought out ideas bouncing around up in here. But, it's when you sit down and you have to write it out that you're forced to think right. Like, writing forces you to think right.”

Diogenes the Cynic, when asked why he changed his mind about something he used to believe, responded with an analogy to childhood incontinence: 'There was a time I used to piss my bed, but not any longer,' illustrating that changing one's mind is good and a sign of growth and maturity.

“The philosopher Diogenes the Cynic was once asked about why he changed his mind, why he didn't believe something that he used to believe. And he said, 'You know, there was a time that I used to piss my bed, but not any longer.' It's good to change their your mind. It's good to grow. It's good to say, 'Hey, this is what I used to believe, this is what I used to do. That was wrong and now I think X, Y, or Z.' That is a sign of growth and maturity and of getting better.”

Seneca taught that one should read dangerous ideas like a spy in the enemy's camp—not limiting oneself to agreeable sources, but seeking out ideas that are different and challenging because this makes one better and stronger.

“And Seneca talked about this very idea. He said, 'We should read dangerous ideas like a spy in the enemy's camp.' We don't just read what we agree with. We don't just hear from people who are like us or from the have the same background as us, but we want to seek out things that are different. Seek out things that challenge us, because this makes us better and it makes us stronger.”

People typically treat opponents as caricatures (strawmanning), picking the weakest and most ridiculous version of the opposing view to argue against; wise people instead steelman—understanding the strongest version of an opponent's position, sometimes better than the opponent can articulate it.

“Most people treat their enemies or their opponents as caricatures, right? They that that's what's called making a straw man argument. You pick the weakest, most ridiculous thing that you think they might believe and then you're opposed to that. But wise people do the opposite. They steel man. They go to actually understand, why does that person think that? What does it mean? What's the strongest argument they can make? Maybe you can even make a stronger argument for their position than they can.”

Seneca himself said that the mind must be given over to long wandering walks and is nourished by the outdoors; this is something ChatGPT and technology will never be able to replace—the getting outside, getting inspired, working through things.

“Seneca himself said that the mind must be given over to long wandering walks. He said it was nourished by the outdoors. One thing ChatGPT and technology will never be able to do is to replace that. The getting outside, getting inspired, working through things. The human mind is meant to be on the move. So, get out there, get moving. It will make you a better thinker. It will also make you happier and more connected.”

If one finds oneself constantly in opposition to everyone and most consensuses, this is likely a sign that insufficient thinking is happening and one is being reactionary and emotional rather than thoughtful; such chronic opposition signals intellectual laziness, not intelligence.

“In fact, if you find yourself constantly in opposition to everyone and to everything, right, or most consensuses, probably a sign that you're not doing enough thinking, right? You're just being reactionary and emotional and I would say also obnoxious and annoying because you think that's what an intelligent person would do. But you're actually not doing anything intelligent at all.”

The work of developing thinking, learning, and wisdom is not just foundational work done once at the beginning, but ongoing work one must continuously do, day in and day out, indefinitely.

“So, we must understand that ultimately this stuff is a lot of work. It's not just the basis kind of work you have to do at the beginning, but it's work you have to keep doing. You have to keep going. You have to keep learning. You have to keep thinking day in and day out.”

When researching his book on Lincoln, the speaker initially believed he knew enough about the subject, but discovered he needed to read multiple thousand-page books, write hundreds of pages of analysis, interview people, and read primary documents before understanding the topic deeply enough.

“on the wisdom book, I was I was going to write about Lincoln and I thought I knew enough about Lincoln to make this chapter work. And as I got in into it, I realized I didn't and I had to read a thousand-page book and then another thousand-page book and then another thousand-page book. I I had to add to that knowledge hundreds and hundreds of pages of writing. I had to interview people. I had to read primary documents.”

Awareness of widespread incompetence and unreliability among experts and systems allows one to recognize when one is being fooled, lied to, or deceived, and thus to 'think for yourself' by not deferring uncritically to authority.

“And going in with that assumption allows you to know when you're being fooled, when you're when when someone's trying to pull one over on you, or when someone is just absolutely full of it. Which is why you have to think for yourself.”

Pretentiousness and condescension—pride in reading obscure texts or demonstrating mastery of dense philosophy—are intellectual traps that cause one to miss the point; people waste their lives becoming experts on arcane things of no significance while adopting airs of superiority.

“Pretentiousness makes you stupid. Condescension, it is often a way that we hoist ourselves upon our own petard. Epictetus once hears this student talking like really proudly about having made his way all the way through the works of Chrysippus. Chrysippus being a a pretty dense early Stoic writer. And so, Epictetus with a smile says, 'You know, if Chrysippus had been a better writer, you'd have less to brag about.' The idea of, 'Oh, I read these obscure things. I can make my way through these dense things.' Like, being a literary snob is to miss the point. People waste their whole lives trying to become experts on things that don't actually matter, that have no significance.”

Our immediacy biases often lead us astray; we need to zoom out and focus, as Jeff Bezos said, on things that don't change—not trendy or popular things, which are likely to become obsolete, but timeless, stable aspects of domains.

“So, our immediacy biases often leading us astray, right? We need to zoom out. We need to focus as Jeff Bezos, the founder of Amazon, famously said, on the things that don't change. Right? When you're thinking about what you're going to study, what you're going to learn, what you're going to get good at, you don't just want to focus on what's trendy and popular right now, because chances are that thing is not going to be trendy or popular in the future.”

Being a contrarian for its own sake is dangerous and stupid; it is not thinking for yourself to simply take majority opinion and invert it; rather, one must go to first principles with one's own knowledge and expertise to determine what is actually true.

“So, you might think that what I'm saying is that you should be a contrarian. But, this is actually really dangerous. And I once interviewed Peter Thiel, the the billionaire who's widely considered to be a contrarian, and I asked him about that. And he said that that he didn't see himself that way. And that actually being a contrarian is a stupid thing to be. He said that it's it's it's dangerous to just take what everyone else is thinking and put a minus sign in front of it or just flip it, just be like, oh, here's what they think I want to think the opposite.”

Peter Burke, one of Montaigne's biographers, believed that Montaigne's essays were his attempt to catch himself in the act of thinking—to think about what he thought, to determine what he actually did or didn't know.

“Peter Burke, one of Montaigne's biographers, believed that Montaigne's essays were his attempt to catch himself in the act of thinking. It was to to think about what he thought, to to to get to what he actually did know or didn't know.”

Charles Duhigg has written about supercommunicators in his book 'Supercommunicators'; supercommunicators are not primarily amazing orators or inspiring speakers, but rather people who are exceptionally good at asking good questions.

“I interviewed Charles Duhigg. He has this great book called Supercommunicators. And supercommunicators aren't these amazing orators who just get up and give inspiring speeches. No, what what most supercommunicators are really good at is asking good questions.”

One will not get better without asking questions and being curious; if one is not good at asking questions or cannot craft good questions, one cannot benefit from large repositories of knowledge like ChatGPT and Gemini, even though these systems contain vast amounts of good information.

“You will not get better without asking questions, without being curious. And this goes right to the idea of ChatGPT and Gemini and all these AI software. Like, there is a lot of knowledge in there. There is a lot of good stuff in there. If you're not good at asking questions, if you can't craft a good question, right? If you're not curious, you can't benefit from all that. You can't learn from it. So, this is a skill we have to cultivate.”

The speaker learned from Robert Greene (while working as his research assistant) a specific process: underline passages while reading, fold those pages, take notes, then transfer that knowledge into a commonplace book, which is then used in real life.

“I learned this from Robert Greene when I was his research assistant. When I read things, I I underline, then I fold those pages, and then I I take notes, and then I transfer that knowledge into my commonplace book, which I then use in my real life.”

One should think for oneself, challenge orthodoxy and convention, and go to first principles because the crowd and tradition are often not the best way; as Mark Twain said, when on the side of the majority, pause and reflect.

“It is important to think for yourself. It is important to challenge orthodoxy and convention. It is important to go to first principles, because you find out that often the crowd, often most people, the way we've always done things, is not the best way. And in fact, as Mark Twain said, 'When you're on the side of the majority, pause and reflect.'”

Stockdale's father taught him that you cannot compete against something you don't understand; if you are fragile and cannot be challenged, you will find yourself in trouble when actually challenged.

“this jives with one of the things that his father had taught him, that you you can't compete against something you don't understand. And if you're a fragile little snowflake that can never be challenged, you're going to find yourself in real hot water when you actually are challenged.”

One should spend time with people smarter than oneself, who know more, from whom one can ask questions and learn, and who challenge one's thinking; cultivating a group of such people is essential, and actively putting oneself in rooms where one is not the smartest person makes one smarter.

“You want to spend time with people who are smarter than you. You want to spend time with people who know more than you. People you can ask questions to, people you can learn from, people you can aspire to be like. You want to be around people who think differently than you, who challenge you. And and so, cultivating that group of people is really important. Actively putting yourself in rooms where you are not the smartest person will make you a smarter person.”

You must monitor your information diet and cut out things that are fun or entertaining but not good for you, and actively consume ideas and sources that are like 'metaphorical fruits and vegetables'—not always enjoyable but best for your intellectual health.

“you have to monitor your information diet, and you have to cut out things that might be fun or entertaining, but are not actually good for you. And you have to consume those like, you know, metaphorical fruits and vegetables that are not always fun to eat, don't always taste the best, but are best for you.”

The speaker has never taken a walk without coming back with an idea or clarity, and has never regretted taking a walk; walking is always beneficial.

“I don't think I've ever taken a walk and not come back with an idea, come back with some clarity. And I've certainly never taken a walk and not come back and thought, 'I'm really glad I did that.' Always better to do that.”

Kierkegaard famously wrote in the morning and then took long walks to work through what he had just written and thought about, using walking as a tool for processing and refining ideas.

“Kierkegaard famously would write in the morning and then take a long walk to work through what he had just worked on and thought about.”

The speaker has directly observed that ChatGPT, pundits, talking heads, and Reddit comments are generally very bad sources of information and low-quality, which the speaker knows because they are a subject matter expert in some domains where they see the errors clearly, but they then reasonably infer those same sources are likely unreliable in domains where they are not expert.

“I see this with ChatGPT, I see this with pundits and talking heads. I I even see this like in the comment section on Reddit or whatever. These people are just really bad. They're just The answers are not good. The quality of information is not high. That's very clear when I am an subject matter expert on that thing.”

Focusing on humility, staying grounded, and prioritizing things that really matter is essential; these are the keys to good thinking, in contrast to intellectual snobbery or debate over arcane points.

“To me, humility is the key, being down-to-earth is the key, and focusing on the things that really matter is the key.”

The speaker has been keeping a commonplace book for 20 years and draws on it in writing, parenting, entrepreneurship, and life generally; the idea that one can draw from memory alone, without collecting and organizing insights, is naive because human memory cannot retain all previous exposures and knowledge.

“I've been keeping a commonplace book going on 20 years now. And I draw on it in my writing, I draw on it as a parent, I draw on it as a human being, I draw on it as an entrepreneur. The idea that you're just going to draw from memory all the things that you've ever been exposed to or or known is just naive at best.”

Reading classical works provides a longer-term historical perspective; seeing ideas that were relevant 2,000 years ago still relevant today reveals how much longer events (like the Antonine Plague, lasting 15 years) and processes (like Rome's fall, taking 300+ years) actually take, correcting modern immediacy bias.

“One of the things you get when you read the Eternities, as Thoreau said about the classics, is you get a longer-term perspective. You're reading something that was relevant 2,000 years ago, and you see, 'Oh, it's still relevant today.' Right? It gives you a larger sense of time. Like, do you know how long the Antonine Plague lasted, the the plague that happened during Marcus Aurelius's reign? It wasn't like 3 years, like COVID. It was 15 years. And you go, 'Oh, wow, he had to deal with this issue for a very long time.' Or take something that people evoke all the time, right? The Decline and Fall of the Roman Empire, right? People think maybe America is in the middle of that right now. But do you know how long the fall of the Roman Empire took? It took at least 300 years.”

Churchill exemplified the ability to venerate tradition while ridiculing convention—knowing which tried-and-true things are worth preserving and which are outdated and should be questioned; this skill is rare and distinct from blanket traditionalism or blanket modernism.

“There's actually a great observation about Churchill that I think connects here. It was said that Churchill venerated tradition but ridiculed convention. It's the ability to know which tried and true things are worth sticking with and which ones are silly and outdated and should be questioned.”

Powerful and successful people are rarely told when they are wrong, creating a feedback gap; as an emperor with 50 legions, one is structurally 'always correct' in interactions because others cannot afford disagreement, a paradox that removes a key mechanism for error correction.

“You can imagine that not many people could tell the emperor of Rome that he was being dumb, that he was being incorrect. There's a famous exchange between Hadrian and one of his philosophical advisors and they're arguing over something that hasn't objectively right or wrong answer. But in the end the philosopher goes, you know what, sir, you're correct. And the philosopher's friends come up to him afterwards and and say, why did you do that? You were right. And he said, I think you forget that the man who controls 50 legions is always correct. Right? This is the paradox of power or success. People are much less likely to tell you when they are wrong and you get out of the habit of admitting you were wrong and correcting error.”

The wisest people maintain inputs and consume information that runs contrary to their beliefs; living in a filter bubble isolates one from the corrective force of opposing views.

“It is so easy to live in a filter bubble, but the wisest people have inputs and get information that runs contrary to what they think and believe.”

Having the Daily Stoic podcast has improved the speaker's interviewing and questioning skills, helping him learn to ask people questions to understand what they believe and to transfer what is in their brain into his.

“Having the Daily Stoic podcast has made me get better at interviewing, asking people questions, trying to to get to what they believe, to to find out how I can get what's in their brain into my brain.”