You must know by now: I don’t believe that philosophy is something for the classroom. It’s something that helps you with life. It shouldn’t be complicated. It shouldn’t be confusing. It should be clear, and it should be usable. As Epicurus put it, “Vain is the word of the philosopher which does not heal the suffering of man.”

Some of the best philosophers never wrote anything down; they just lived exemplary lives and provided an example which we can now learn from. That was philosophy. It was practical and it was applicable and it made life better. But thankfully some philosophers were doers and writers, and the books below will help you understand the words that they lived by—and hopefully apply them to your own opportunities, obstacles, and experiences.

Meditations by Marcus Aurelius

It still strikes me now, some 17 years into reading this book, how lucky we are to even have it. Meditations is perhaps the only document of its kind ever made: the private thoughts of the world’s most powerful man about how to make good on the responsibilities and obligations of his positions. Marcus stopped almost every night to practice a series of spiritual exercises—reminders designed to make him humble, patient, empathetic, generous, and strong in the face of whatever he was dealing with. You cannot read this book and not come away with a phrase or a line that will be helpful to you next time you are in trouble. Read it, and then read it again as often as you can. (Note: I strongly recommend Hays’s translation above all others. I loved it so much we created a leatherbound version to withstand the test of time for The Daily Stoic.) And if you end up loving Marcus, try The Inner Citadel and Philosophy as a Way of Life by Pierre Hadot. Hadot is maybe one of the smartest people I’ve ever read. The Inner Citadel is mostly about Marcus Aurelius and the Stoic concept of the self as a fortress. Philosophy as a Way of Life is essentially a book about the wisdom of ancient philosophers cumulatively acquired and how we can use the same exercises in our struggles. Also Memoirs of Hadrian by Marguerite Yourcenar. There are not many great works of fiction about Stoicism, but this is one. Written from the perspective of Hadrian, the book takes the form of a long letter of advice to a young Marcus Aurelius, who would eventually succeed him as emperor. It’s somber but practical, filled with beautiful and moving passages from a man near death, looking to prepare someone for one of the most difficult jobs in the world.

Letters from a Stoic by Seneca 

Seneca, like Marcus, was a powerful man in Rome. He was also a great writer and from the looks of it, a wise man who dispensed great advice to his friends. Much of that advice survives in the form of letters, guiding them and now us through problems with grief, wealth, poverty, success, failure, education and so many other things. Seneca was a Stoic as well, but like Marcus, he was practical and borrowed liberally from other schools. As he quipped to a friend, “I don’t care about the author if the line is good.” That is the ethos of practical philosophy—it doesn’t matter from whom or when it came from, what matters is if it helps you in your life, if only for a second. Reading Seneca will do that. (Other collections of his thoughts are great too. Penguin’s On the Shortness of Life is excellent, and if you’re looking for an audiobook of Seneca, try Tim Ferriss’ edition of The Tao of Seneca: Letters from a Stoic Master.) I also recommend The Greatest Empire: A Life of Seneca by Emily Wilson. Wilson’s translations of Seneca are excellent and her insights are provocative. Must read for any student of history or philosophy.

Enchiridion by Epictetus 

Unlike those two powerful Stoics, Epictetus overcame incredible adversity. A slave who was banished from Rome, he eventually became a philosopher and opened a small school. Notes from his classes survive to us in what is now called the Enchiridion, which translates as a “small manual or a handbook,” and it is exactly that. It is the perfect introduction to Epictetus as it is packed with short Stoic maxims and principles. Unlike both Seneca and Marcus, Epictetus is somewhat more difficult to read, and I recommend beginning with those two if you haven’t yet read them. The next step would be Epictetus’ Discourses, which are much longer and deserve a bigger commitment. And for more related to Epictetus, you can look into the short autobiography Courage Under Fire by James Stockdale. We interviewed James Stockdale’s son, Sid Stockdale, on the legacy of his father. You can listen to that episode here.

That One Should Disdain Hardships: The Teachings of a Roman Stoic by Musonius Rufus

Unfortunately, most of the works of the Stoics not named Epictetus, Seneca or Marcus Aurelius have been lost to history. Others are poorly translated or organized. Musonius Rufus has been neglected for both these reasons, but this new book is a great step forward into making him accessible to modern readers. He’s very quotable and very direct—tellingly, the opening essay is That There Is No Need of Giving Many Proofs for One Problem. His most provocative belief in first-century Rome? That women deserved an education as much as men. Two of Musonius’s 21 surviving lectures (That Women Too Should Study Philosophy and Should Daughters Receive the Same Education as Sons?) come down strongly in favor of treating women well and of their capabilities as philosophers. He wrote movingly on companionship, love, and marriage (What Is the Chief End of Marriage and Is Marriage a Handicap for the Pursuit of Philosophy?). Musonius was exiled at least three, possibly four times. He knew about losing your freedom. He knew that all a philosopher could do was respond well—bravely, boldly, patiently—to what life threw at us.

The Moral Sayings of Publius Syrus by Publius Syrus

A Syrian slave in the first century BCE, Publius Syrus is a fountain of quick, helpful wisdom that you cannot help but recall and apply to your life. “Rivers are easiest to cross at their source.” “Want a great empire? Rule over yourself.” “Divide the fire and you will sooner put it out.” “Always shun that which makes you angry.” Those are a few I remember off the top of my head. But all of them are good and worthy of re-reading in times of difficulty (or boredom or in preparation of a big event).

Fragments by Heraclitus

The Stoics, especially Marcus, loved to draw from Heraclitus, a mystic, ephemeral philosopher whose beautiful fragments are eminently quotable. My favorite line from Heraclitus is his line about how no man steps in the same river twice—because it is not the same river and he is not the same man. Another favorite: “Applicants for wisdom / do what I have done: / inquire within.” And of course, his most direct and timeless remark: “Character is fate.” If you’re looking for philosophy that is poetic but also practical, give Heraclitus a chance.

Man’s Search for Meaning by Viktor Frankl

A man is sent to a concentration camp and finds some way for good to come of it. He uses it to fashion a set of principles for life: we have little control over our circumstances, complete control over our attitude, and the ability to make meaning out of the things which happen to us. In Frankl’s case, we are lucky that he was a brilliant psychologist and writer and managed to turn all of this into one of the most important books of the 20th century. I think constantly of his line about the man who asks, “What is the meaning of life?” The answer is that you don’t get to ask the question; life is the one who asks and we must reply with our actions. I was stunned to find that a new (lost) book from him was published in 2020, with a beautiful title worthy of a daily mantra, “Yes to Life: In Spite of Everything.” 

Essays by Michel de Montaigne

Montaigne was deeply influenced by some of the books I mentioned above. He was the epitome of Heraclitus’s line about “inquiring within,” so much so that he spent basically the entire second part of his life asking himself (and other people) all sorts of interesting questions and then exploring the answers in the form of short, provocative essays. (A favorite: Whether he was playing with his cat, or whether he was the toy to his cat.) These essays are always good for a helpful thought or two—be it about death, “other” people, animals, sex, or anything. Also, read Stefan Zweig’s Montaigne. I think it is one of the most beautiful biographies ever written. It’s a book about a man who turned inward as the world was tearing itself to pieces… written by a man forced to do the very same thing some 350 years later. It is timely and important. 

Nature and Selected Essays by Ralph Waldo Emerson

While Montaigne’s essays are good for making us think, Emerson’s essays make us act. They remind us that we are ultimately responsible for our own life, for making ethical choices and for fulfilling our potential. Unlike most classic writers, Emerson embodies that uniquely American mix of drive and ambition (but in a healthy way). If you have not read Emerson, you should. If you have—and you remember fondly his reminders about recognizing our own genius in the work of others, or his reminders to experience the beauty of nature—that counts as philosophy. See how easy it is? Also, read Walden by Emerson’s friend and protégé Henry David Thoreau. Thoreau did what everyone who has ever lived a normal life has considered doing at least once: he ran into the woods. He retreated into solitude on Walden Pond where he built himself a tiny cabin, in which he lived alone for two years. Thoreau immortalized those two years and the lessons he learned in Walden, concluding with why you can put to bed any considerations of escaping to the woods.

The Art of Happiness by Epicurus

Epicurus was a rival to the Stoics… and today, both schools rival each other for the title of most misunderstood school of philosophy. Epicureanism is not hedonism. In fact, Epicurus preaches restraint and self-discipline. “The pleasant life is not the product” of drinking and sex, Epicurus said; “On the contrary, it is the result of sober thinking—namely investigation of the reasons for every act of choice and aversion and elimination of those false ideas about the gods and death which are the chief source of mental disturbances.” That being said, Epicurus was much more explicit about joy and happiness than Epictetus or Marcus Aurelius. The Epicureans were less concerned about duty and honor and other earthly obligations—they were more Eastern in that way. They were also pithier, in my opinion. Which is probably why Seneca joked, after quoting Epicurus, “I don’t mind quoting a bad author if the line is good.” Anyway, read this… and it’s probably OK to skip the stuff about atoms. 

Plutarch’s Lives and Plutarch’s Moralia

Is there anyone better than Plutarch? No, there is not. I think he’s the best, most interesting, most accessible biographer to ever do it. There’s a reason he was the favorite of everyone from Napoleon to Alexander Hamilton right on down to people today. Funny enough, his grandson was one of Marcus Aurelius’s philosophy teachers. Anyways, he’s hard to beat. If you haven’t read Plutarch, do it! Try Penguin Classics; or the little translation How to Be a Leader from Princeton Press is also good. 

The Tao Te Ching by Laozi

It’s fascinating that both Epictetus and the Tao Te Ching at one point use the same analogy: The mind is like muddy water. To have clarity, we must be steady and let it settle down. Only then can we see. Only then do we have transparency. Whoever you are and whatever you’re doing, you would benefit from having more of this clarity. The Tao Te Ching is made up of 81 short chapters, a mixture of poetry and prose aimed at giving you that clarity. Also read Readings in Classical Chinese Philosophy by Philip J. Ivanhoe. Don’t dismiss it over the boring title! The book is an amazing anthology of the best of Eastern Chinese philosophy (most of it pre-Zen Buddhism). I folded so many pages reading it that I dreaded having to transfer my notes to notecards. It took forever, but it was worth it. This is a great introduction to Confucius, the Tao Te Ching, and other important texts. I also like Buddha by Karen Armstrong. It’s scholarly without being pedantic, inspiring without being mystical. Armstrong is actually a former Catholic nun (who teaches at a college of Judaism), so I loved the diverse and unique perspective of the author. And Armstrong never misses the point of a good biography: to teach the reader how to live through the life of an interesting, complicated but important person. 

Zen in the Art of Archery by Eugen Herrigel 

I was sitting back taking notes after my reading of both these books when my wife yelled “HOGS!” I rushed downstairs, grabbed my rifle, and as I walked slowly through the trees towards the small pack of wild hogs, I practiced both the breathing exercises in the book and the art of letting the shot fall from the weapon (rather than being forced). It was a rather perfect moment—and so too was the delicious boar sausage I had made afterwards. Of course, Master Kenzo would say that whether the shots hit their mark (three of four did) is irrelevant. What mattered was the moment and the practice. Because this is ultimately not a book about archery, but about zen, and the mastery of the soul. Also read The Way of Baseball: Finding Stillness at 95 mph by Shawn Green. It’s a great, accessible book about peace and peak performance that doesn’t hit you over the head with Buddhism, yoga, meditation or any of that. It’s about how Shawn Green struggled as a major league baseball player and through repetitive simple practice turned himself into one of the best home run hitters in the game. And Sadaharu Oh: A Zen Way of Baseball by Sadaharu Oh. As a testament to my embarrassing American-ness, I hadn’t heard of Sadaharu Oh until a baseball coach I know mentioned him (and therefore didn’t know he was a better home run hitter than Babe Ruth or Hank Aaron or Barry Bonds). It turns out that in addition to being an incredible athlete, he’s also a beautiful writer and storyteller. I’ve recommended and written about Musashi before—well, Sadaharu actually designed his infamous swing around the teaching of Musashi (famously practicing swinging at pitches with a sword). This book was great. It’s a memoir more than it is a book about baseball, so even if you don’t like sports, I promise you will get a lot out of it.

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And one final recommendation…

I’ve talked a bit about Marcus Aurelius here and why we should study the LIVES of the Stoics. Well, one more short read for you: The Boy Who Would Be King.

It’s one of the most incredible stories in all of history. A young boy, out of nowhere, is chosen to be the emperor of most of the known world. How did he do it? What did he need to learn? Who taught him? What do his experiences teach us? I answer those questions in my first illustrated fable, which I’m so excited to tell you is available for preorder: The Boy Who Would Be King. It’s an ageless story of Stoicism… for all ages… and it happens to be printed right here in the US. You can preorder it directly here, and there are signed copies as well.