Today’s Chapter is based on the book “Wisdom Takes Work: Learn. Apply. Repeat. (The Stoic Virtues Series)” by Ryan Holiday.
Ryan Holiday is an American author best known for popularizing Stoic philosophy for modern readers. He wrote books like The Obstacle Is the Way, Ego Is the Enemy, and The Daily Stoic, and is widely known for turning ancient ideas about discipline, courage, and resilience into practical advice.
Here’s what I learned:
Perpetual Learner
“Anyone who stops learning is old, whether at twenty or eighty. Anyone who keeps learning stays young.”
— Henry Ford
The first lesson we can learn from Ryan Holiday is the fact that wisdom is not granted, it must be learned and the learning never ends. He argues that education is not solely delivered by institutions and schools but something that one must continue to pursue. He reminds us that genuine learning is a lifelong commitment that we must take into our own hands. The moment we believe we have finished our education is the moment we begin our decline into ignorance and stagnation. He writes, “We must get it ourselves. No one can give us an education. The most important decision a person makes is to become a student and to remain one not just in school or in their profession, but for life.”
With this idea in mind, Holiday mentions that we can learn from everything. The classroom expands to include everything surrounding us, such as the people around us, the ordinary moments of an ordinary day and even people from history.
The famous French philosopher, Michel de Montaigne, was known to have grown up in a household that allowed family members to discuss everything at the table. Everything became materials for discussions and nothing was exempted from examination. Holiday notes that “In the Montaigne household, everything was an opportunity to learn—even pranks or mistakes were material for discussions or lessons. Everything was designed to ‘serve as an excellent book,’ every situation provided a takeaway, even ‘some cheating by a page, some stupidity on the part of a lackey, something said at table,’ was a chance to discuss, to debate, to analyze.”
“Wisdom, then, is a lagging indicator of work done long ago, the fruit nurtured from seed planted long ago. And, as the ancients taught us, we can only reap what has been sown.”
— Ryan Holiday
By consequence, Holiday emphasizes that in order to obtain wisdom, we must cultivate a powerful sense of curiosity and an insatiable desire to acquire knowledge. This isn’t passive consumption of information but an active engagement with ideas, people, and experiences. This will demand both discipline and courage because the responsibility of learning ultimately relies on us. No one else can supply the hunger or the persistence required to keep learning.
As a matter of fact, the engine of real knowledge must be kept alive through curiosity and asking questions. One example of this is the Wright brothers. Holiday explains that their home was filled with books and their father encouraged them to engage into intellectual exploration, even if it didn’t lead to anything profitable. As Orville Wright once said, “If my father had not been the kind who encouraged his children to pursue intellectual interests without any thought of profit, our early curiosity about flying would have been nipped too early to bear fruit.”
Luckily, curiosity is accelerative: the more we know, the more we want to know. This is the reason why children are learning so quickly. They have the impulse to be consistently asking questions. Questions themselves are tools of learning. There are no dumb questions, only the failure to ask them. The person who stops asking has already decided that the world is fully known, an arrogance that guarantees stagnation. Curiosity is not a childhood phase to be outgrown but a lifelong practice that must be deliberately protected against the pressures of adulthood, routine, and the false confidence that comes with accumulated credentials. Without it, learning slows to a halt and discovery becomes impossible.
“Questions are the key not just to knowledge but to success, discovery, and mastery. They’re how we learn and how we get better.”
— Ryan Holiday
This reminds me of what we have learned from Henry Ford who did not believe that one’s knowledge be judged by their formal education. As he once said, “An educated man is not one whose memory is trained to carry a few dates in history—he is one who can accomplish things. A man who cannot think is not an educated man however many college degrees he may have acquired.”
Furthermore, he believes that one’s education starts after graduation, as the main goal of education “is to teach him how to use his mind in thinking.” As such, when Henry Ford was running the Ford Motor Company, Ford never hired any experts or men with past experiences. His reasoning was that “A man who knows a job sees so much more to be done than he has done, that he is always pressing forward and never gives up an instant of thought to how good and how efficient he is. Thinking always ahead, thinking always of trying to do more, brings a state of mind in which nothing is impossible. The moment one gets into the “expert” state of mind a great number of things become impossible.”
“But the best that education can do for a man is to put him in possession of his powers, give him control of the tools with which destiny has endowed him, and teach him how to think.”
— Henry Ford
Talking to the Eminent Dead
“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 will work better in life and work better in education. It’s way better than just giving the basic concepts.”
— Charlie Munger
Holiday insists that reading is perhaps our most powerful tool for learning. He coins reading as our superpower ability to talk with the eminent dead. This concept comes from the story of Zeno, the founder of Stoicism, who received his calling through an encounter with the Priestess of Delphi.
Holiday writes, “As he wound along the Sacred Way, toward the Temple of Apollo, home of the Oracle at Delphi, he began the sacred rituals, washing his hands in the holy spring. He lit a stick of incense. The flickering light of torches lined his path to the inner sanctum, where the priestess waited for his question. What is the secret to a good life? ‘You will become wise,’ the priestess told Zeno, ‘when you begin to have conversations with the dead.’“
As such, we should see books as our connection to the greatest minds in history. Reading allows us to learn from people we could never meet in person and to absorb their wisdom, mistakes and insights. Ryan Holiday challenges us to take this super power seriously and to start reading. Read old books and new ones, books you agree with and books that offend you, books that confirm your experience and books that overturn it.
“We all have time to read. We just don’t do it enough. It’s about the craziest thing in the world. Imagine having a superpower—being able to talk to the dead—and not using it! Imagine being able to talk with the wisest people who ever lived, as Tolstoy said, and not doing it!”
— Ryan Holiday
Holiday mentions that many successful people from presidents, to generals to inventors, all understood this essential lesson. In fact, Charles de Gaulle read two or three books a week even when he was leading France during World War II. Similarly, General Mattis protected an hour a day for reading even in wartime. As he once said, “It doesn’t matter that we can read. If we don’t, we are choosing to be functionally illiterate.”
Nonetheless, Holiday warns us that solely reading is not sufficient, it must be active. He emphasizes that great readers aren’t simply consumers of information but active participants having a conversation with the author. John Adams was well known for covering the margins of his books with thousand of words of argument or approval.
This payoff is cumulative. Each book becomes a conversation partner that can be summoned years later when a parallel situation arises, as Harry Truman figured out with his copy of Plutarch’s Lives. Considering this, Holiday argues that reading multiplies the number of lives one can live and increase the range of experiences one can draw upon without having to suffer every hard lesson personally. It is the cheapest and most reliable form of mentorship available to anyone who will simply open a book and read.
“Because reading is a conversation, great readers are not passive. They put books through the wringer, they put the author on trial. They ask questions. They talk back.”
— Ryan Holiday
This reminds of me of an interesting anecdote from Benjamin Graham. He made friends with the characters he met from his readings. As he explains, “The real friends and intimates of my life have been Hadrian and Severus and countless other characters of history—even Gustavus Adolphus and Oxenstierns of Sweden—together with those writers whose work and personalities had a special meaning for my developing youth.”
This is similar to Charlie Munger’s concept of making friends with the eminent dead. One of Charlie Munger’s life principle is the idea that the way of learning something is to learn from what others have already mastered. In this way, you can learn from the mistakes and experience of those that came before you. As Isaac Newton once said, “If I have seen further it is by standing on the shoulders of Giants.”
“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 will work better for you in life and work better in education. It’s way better than just giving the basic concepts.”
— Charlie Munger
Funnily enough, both Charlie Munger and Benjamin Graham had the same hero: a certain Benjamin Franklin. As Graham explained, “But while Ulysses has ever been my fantasy idol, there is another fleshand-blood character after whom I have consciously modeled my life. By coincidence we have the same first name. The man is Benjamin Franklin. He had all the characteristics to which I aspire-high intelligence, application, inventiveness, humor, kindness, and tolerance of others’ faults.”
Stay Humble
“On the highest throne in the world, we still sit only on our own bottom.”
— Michel de Montaigne
If there is one enemy to wisdom, it would be ego according to Ryan Holiday. The belief that we already know everything and that we have nothing left to learn is the easiest path to foolishness. Holiday believes that intelligence and formal education may make us more susceptible to stupidity if we let them inflate our sense of certainty. He writes, “The most dangerous thing that can happen to the smartest person in the world is to start to believe that they are the smartest person in the world. It turns them into a very dangerous fool. Because they start to think everything they do is smart, even when it’s dumb.”
This is a reminder that intellectual humility is essential in order to seek for wisdom. This lesson can be found from stoicism, which understood that our perceptions are often unreliable and that we must constantly test them against reality. Holiday notes, “The Stoics knew it was hard work to be on guard against misperceptions. They said we have to take every impression and put it to the test, trusting neither our emotions nor our thoughts. We need to review, to question, to ensure that we aren’t falling prey to well-worn patterns or false promises. We need to make sure we aren’t fooling ourselves... and we have to understand that we are very easy to fool.”
This is the reason why Roman emperor, Marcus Aurelius, kept a journal, as a method of examining his own thinking.
“And that’s what he was doing in Meditations, in his own notebook. He ran tests against his thinking, making his mind do its job through his pen, instead of defaulting to assumptions or first impressions. It takes real work to guard against our biases. It takes strength to remain open, especially as the years go by. We get tired. We get entitled. We get used to knowing better.”
— Ryan Holiday
Holiday believes that one way to fight against our ego is to have the willingness to change our minds and to seek out criticism. He argues that “Wisdom is the ability to go through life ready to change your mind. This doesn’t mean we abandon our values because they’re inconvenient, but our thinking is supposed to evolve. We are supposed to grow. New things are going to come to light. Feedback follows belief and action, which should create new beliefs and actions.”
This is obviously harder than it looks due to preconceptions and biases. As Seneca once said, “Many people could have achieved wisdom if they had not imagined they had already achieved it.” One way to defeat our ego is by admitting to oneself that there’s nothing wrong in being wrong. Holiday reiterates that “Being wrong is not the sin. Being confidently wrong? That’s the problem. That’s the difference between ignorance and stupidity. The ignorant are not nearly as dangerous as the smug and arrogant morons who feel entitled to tell others what to do.”
Luckily, the wiser a person becomes, the less need there is to feel wise. Experience tend to shrink the ego, not enlarge it. As Socrates once said, “The more I know, the more I realize I know nothing.”
This reminds me of what we have learned from Don Valentine, the founder of Sequoia Capital, who approached business and investing with an unwavering commitment to questioning everything, a habit that was rooted in his early education and experiences. By having a skeptical mindset, he was able to cut through noise, identify opportunities and avoid pitfalls. Valentine questioned everything in order to foster a deeper understanding through persistent inquiry.
The Socratic method became one of Valentine’s core reasoning when evaluating ideas, markets, and people at Sequoia Capital. In fact, this constant approach of questioning everything made Valentine dislike any policies and procedures, as he believed that rigid structures stifled creativity. An example to illustrate this was the fact that Valentine always used to wear his nametag on his right breast at functions while the convention was to wear it over the left.
“It’s disobedience that gets you innovation.”
— Don Valentine
For Valentine, the ability to admit ignorance was a sign of strength, creating space for genuine learning and discovery. He sought this humility in others, famously filtering out candidates who overused “I” instead of “we.” This foundational habit of mind to constantly ask “why” and to have the courage to say “I don’t know” protected him from the herd mentality and allowed him to see potential where others saw only implausibility.
Beyond the Book
Read "Lifelong Learning" by Farnam Street
Read "Seneca on Letting the Eminent Dead Guide You" by Farnam Street
If you are interested in having conversations with the eminent dead, consider trying my AI Chatbox prompted with highlights from over 100+ biographies I have read. Try it here.
If you enjoy reading my newsletter, please consider becoming a paid subscriber. You’ll be able to keep this newsletter going! Here’s what you get when you upgrade:
Voting on polls: you’ll get to vote on who I should write about next.
Requesting biographies: you can request a biography for me to read and write about next.
Supporting my next book purchase: all payments received will be used to purchase a new biography.