"Wisdom Takes Work"

Wisdom must be earned and re-earned — a Q&A with author and Stoic thinker Ryan Holiday

“Acta non verba — Deeds not words. All the virtues are supposed to be verbs and not nouns — things that you do.”

That’s author and Stoic thinker Ryan Holiday, on the central idea of his latest book, Wisdom Takes Work. The premise is that wisdom is not something you’re gifted by age or intelligence, but something earned and re-earned through repeated effort.

It felt like an apt topic for the start of a new year. Below is our conversation.

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David Epstein: This is the fourth and final installment in your “Stoic Virtues” series, one book on each of the four virtues — courage, temperance, justice, and now wisdom. I gather you saved wisdom for last on purpose. What are you hoping people take from this final book in the series?

Ryan Holiday: Look, at some point in our life, we’re all going to come to some sort of situation or dilemma or difficult period. Just as you’re going to want to have some resilience to be able to endure this, you’re also going to need wisdom — that is, the experience, the perspective, the creativity, the insights that allow you to understand what this means and what to do about it. You’re going to need that wisdom at some point … and it will be too late to get it.

The main thing we have to understand is that wisdom isn’t this thing you’re born with. It’s not a natural result of old age. It has very little to do with intelligence either. It’s the byproduct of a lot of work. “No man is ever wise by chance,” is how Seneca put it. So I was trying to make a case for doing that work, as I think we are in one of those difficult periods, and part of the reason we are struggling as individuals and as a society is that we lack that wisdom.

DE: Readers aside, what did you get out of writing this book?

RH: This is honestly what I think about most. I try to make sure that on every project I do that I get better. In that way, it’s a success whether it sells two copies or has a nice run on the bestseller lists. This was a series of books for me, so I learned a lot as a writer (and just as a manager of myself) about how to organize and plan and execute something with so many pieces and so many overlapping themes. I’ve been working on it since 2019, so it’s the longest I’ve ever worked on one project. I feel like I grew as a writer to be sure, but I also grew as a person, you know, spending six years with so many wonderful people. I got to spend a half decade with people of virtue since that is who I was profiling. So brave people, disciplined people, people of character, people of incredible wisdom. I think I picked up a lot of that by osmosis, but I guess that’s for others to say.

DE: I think Wisdom Takes Work has some of your best writing. You make great use of repetition, for instance. Right at the start, you give us Hercules at the crossroads of vice and virtue:

“We hear of this moment in the stories of Socrates. We can see it captured in the most beautiful art of the Renaissance. We can feel his budding energy, his strapping muscles, and his anguish in the classic Bach cantata.”

We hear. We see. We feel. The hallmark of modern music is repetition, and to me it gives a rhythmic quality to the writing. Some chapters use lists of acts —virtuous or vicious, ancient or modern — to build toward a crescendo about how to live a life of wisdom. The structure itself feels fractal: three sections, each beginning with a longer introductory chapter, followed by a dozen or so shorter ones. Each chapter builds to a crescendo that contributes to the larger crescendo of its section, and each section to the book as a whole.

It struck me that the structure itself enacts your theme — that wisdom isn’t a single insight but something built through repetition and refinement. Did you intend for the form of the book to mirror the repetitive, lifelong practice of wisdom you describe, or did that rhythm emerge organically as you wrote?

RH: Oh that’s very nice. The funny thing is that those sentences were some of the first things I wrote in the whole series. I guess it would have been in the summer of 2020. Each of the books opens with the same story of Hercules at the Crossroads, which is actually the story that Zeno heard when he ended up in Athens after a shipwreck and was having to rebuild his life. I had never been to Greece, and the story is almost certainly myth, so making it feel real was a challenge. But I was in Greece for a long stint this summer, after all the books were done, and I kept thinking: “Ok, I think I got pretty close.” Especially when I’d go for a run and come to a fork in the road…

I did plan for each of the books to be three parts and for the final part to be the highest form of that virtue. So the Courage book ends with stories of transcendent selfless courage. The Justice book ends with stories of Gandhi and Christ et al. Here’s where I do think it’s fractal or perhaps nested. Virtue is not one thing. According to the Stoics, it’s four: Courage, Temperance, Justice, Wisdom. And then each of those virtues is made up of sub-virtues, obviously. So what I tried to do in the books, and I think I say this in the intro of the first one, is to just take different cuts on them so you’re seeing what virtue (and the virtues) are from all these different angles, but it ends up as one gem.

DE: That rhythm — the repetition and crescendo — really stood out in your chapter on Elon Musk. It starts with a litany of brilliant accomplishments, then flips to a litany of reckless or cruel acts — another crescendo in the opposite direction. What does Musk represent in the context of this book?

RH: I am probably proudest of this section and it was also the most challenging — not just because the person is still alive and extremely litigious, but also because I admire him. Plutarch is one of my favorite writers — maybe the greatest biographer of all time — and he does a brilliant job of just sort of laying his characters out and letting their actions speak for themselves. I realized that actually the strongest case against the monstrous and destructive things that Musk has done these last few years was to contrast them with the incredible creative and innovative things he had done previously. So I just told the story end to end and I tried to really steel-man all the good things he has done. And then the indictment is much clearer. You can’t help but think, “Man, what happened?” And the answer is a lot of things — drugs, ego, social media, bad habits in his personal life, isolation, a profound lack of empathy, etc. The guy that made electric cars viable, the guy that did better than NASA … is also, ultimately, going to be responsible for the deaths of countless thousands of people. One of the smartest people in the world doing and saying things that are incredibly stupid. The richest man in the world stealing food and medicine from the mouths of the poorest. It’s an epic tragedy.

DE: At one point you use a line from Seneca, who said that we should read “like a spy in the enemy’s camp.” What did he mean?

RH: Do you know who Seneca quotes the most in his writings? It’s not any of the Stoics. It’s not Aristotle or Plato or Socrates either. It’s Epicurus. He was intimately familiar with the works of the rival school, and the funny thing is that most of the time when he’s quoting Epicurus it’s to agree! The point is: You gotta get out of your bubble. You gotta read people with differing views. You gotta read people outside your genre, outside your frame of reference. I know this is something I struggle with: None of us read as much as we like, so you’re going to take the time to read something you don’t like? But, yeah, you have to.

DE: To follow up on that, you’ve been outspoken about that idea. Earlier this year, about an hour before you were scheduled to speak at the U.S. Naval Academy — a talk you’d given for several years — you got a call asking that you not mention any of the 381 books that had been removed from the Academy’s library. You declined, and your talk was cancelled. Among the authors with removed books, at least initially, were Maya Angelou and Jesmyn Ward — one of our greatest living fiction writers, in my opinion. It seems especially odd when even Mein Kampf wasn’t removed. But honestly, I think Mein Kampf — which I’ve read — should absolutely be there too. How can you understand history without it?

In a famous dissenting opinion, Justice Oliver Wendell Holmes wrote:

“...the best test of truth is the power of the thought to get itself accepted in the competition of the market…. That, at any rate, is the theory of our Constitution. It is an experiment, as all life is an experiment.”

It strikes me that so much of this book is about continually challenging your own ideas — living, in a sense, in your own marketplace of ideas — rather than becoming increasingly narrow and convinced of the beliefs that come easily. You are writing about this for the individual, but also becoming more outspoken about it on a societal level. How do you see this book, and your broader work, as responsive to our historical moment?

RH: I mean, we’re going to trust these young men and women with aircraft carriers and nuclear submarines but not Maya Angelou? It’s absurd. The library at the Naval Academy has hundreds of thousands of books. The idea that the Secretary of Defense should be removing certain titles for being too woke is not just stupid, it’s honestly lame. Like, doesn’t he have better things to do? And then, and I think this ties into some of the other themes in the series, the leadership at the school didn’t push back on this order — which, in fact, originally did not apply to colleges. They then found themselves in the position of having to suppress [my] talk that was — for two minutes — going to criticize that decision by telling a story of Admiral Stockdale studying Marxism at Stanford and how that helped him when he ended up in a communist prison. I felt I could not in good conscience remove the criticism when I was asked to, as that would be pretty unethical and cowardly. In any case, what was the [Naval Academy] Admiral’s reward for playing ball in this way? She was removed anyway.

The job of the writer is to tell the truth as they see it. It’s not to tell the audience what they want to hear. That obligation is important.

DE: Building on that point, a final question: This is a philosophical book, but it’s very much a book about doing things, not just thinking things. Late in the book, you emphasize deeds. It reminded me of James in the Bible: “Faith by itself, if it does not have works, is dead.” I was just looking at your social media, and I see that when you express dismay at things like book bans, many responses — from apparent fans — criticize you for “not being very Stoic.” They seem to imply that Stoicism means withdrawal from the world. What would you say to people who hold that view?

RH: Acta non verba. Deeds not words. All the virtues are supposed to be verbs and not nouns — things that you do. They aren’t things you have; they are things you do day to day…or not. In a way, it’s sort of like writing. You are not “a writer.” You’re either writing or you’re not. In any case, I try not to think about whether I upset some people from time to time. I know I do but that’s not in my control. It’s worth remembering that it’s usually only the upset people that you hear from. Other people are just living their lives. I try to do my best to be good at my job and be a good person, which I think in this moment means calling a spade a spade. It means being involved politically. It means not being an asshole. It means defending the basic parts of the social contract (to say nothing of the Constitution). And I think it means using your platform to have a positive impact on the world.

Thank you for reading, and thanks to Ryan for his time.

Ryan owns and operates The Painted Porch, a wonderful bookstore in Bastrop, Texas, so of course you can order the book there.

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Hope you’re having a wonderful start to the new year! Until next time…

David