10 Stoicism Books to Help You Overcome ANY Challenge

Get This Book on Amazon: On the Shortness of Life

“It is not that we have a short time to live, but that we waste a lot of it.

Life is long enough, and a sufficiently generous amount has been given to us for the highest achievements if it were all well invested.

But when it is wasted in heedless luxury and spent on no good activity, we are forced at last by death’s final constraint to realize that it has passed away before we knew it was passing.

So it is: we are not given a short life but we make it short, and we are not ill-supplied but wasteful of it.”

-Seneca, On the Shortness of Life

As far as moral essays go, this one from the ancient Roman statesman Seneca is one of my favorites. Written in 49CE, it’s addressed to his father-in-law Paulinus, whom he advises about how to expand time, prevent it from being squandered on nonsense, and use it in the best way we can.

I read this book in 2015, and since then, I’ve probably taken about 5 full years of my life back due to taking Seneca’s advice and rejecting everything that diminishes the value of my time, and placing my focus squarely on where I’m able to experience true fulfillment and purpose.

Spoiler Alert: It’s NOT where modern society keeps dragging your focus back to.

Nothing against society - I love society! - but it’s not set up to help you be happy or fulfilled in any way. Pretty much the opposite, in fact.

You’re born and bred to keep the system going: pay attention, get good grades, get into a good school, pay hundreds of thousands of dollars in student loans, hundreds of thousands more to experience “the dream of home ownership,” etc.

Again, nothing against education or owning your own house.

It’s just that these things are expensive; in money, yes, but also in time. And society’s answer doesn’t have to be your own.

What Thoreau said is true: the price of anything is the amount of life you’re required to exchange for it, and so you can think of On the Shortness of Life as a collection of Seneca’s best arguments against trading your life away for trivialities.

It’ll teach you the true value of time, how little we actually need to acquire and possess in order to experience peace of mind, and how you can defend yourself against the priorities of those who would steal your most important possession and give you back something infinitely less valuable in return.

Get This Book on Amazon: Philosophy as a Way of Life

“Let us assume we say 'Yes!' to one single, unique moment: we have thus said yes, not only to ourselves, but to the whole of existence. For nothing is isolated, neither in ourselves nor in things.

And if, even once, our soul has vibrated and resounded like a string with happiness, all eternity was necessary to create the conditions for this one event; and all eternity has been approved, redeemed, justified, and affirmed."

-Friedrich Nietzsche

If you took a few required philosophy courses in university, hated it, and subsequently wrote off philosophy forever as “not really my thing,” then it probably wasn’t philosophy.

You might have heard some version of this joke where a doctor is asked what he specializes in, and the doctor replies, “I specialize in the treatment of the left earlobe.” The joke is that medicine has become so ultra-specialized and exact - so finely technical - that you could have a specialization like that and no one would know if you’re even joking or not!

Well, it’s kind of the same thing in philosophy nowadays.

It’s become so unbelievably stuffy and academic that you could present a thesis on “Semiotic De-Temporalization in Abstract Existentialist and Metaphysical Meta-Realities” and you’d probably get your doctorate! Did I just make that up? Or is it a real thing?

Who knows!

Anyway, it’s so far away from the actual philosophy that real people used to practice to, you know, improve their lives! Hadot’s book is about real, honest to goodness philosophy (a word that means love of wisdom), and it’s about real people (everyone from slaves to Roman Emperors) who used it to become mentally stronger, more joyful, less afraid, and more fully alive.

I won’t say that this is an easy read because it’s not. It’s more of a philosophy textbook than something you’d bring with you to the beach, but the whole purpose is to show you that philosophy’s a real, live activity, that can actually improve your one and only life.

Reading it, you’ll see why people like Socrates felt that real communication with other human beings was infinitely superior to knowledge gained from books, how Marcus Aurelius used philosophy to help him run the Roman Empire without losing his mind, and how you can go from where you are now, to where you want to be.

Get This Book on Amazon: The Therapy of Desire

“The good person has no need for revenge, since the slights that others take to be harms and damages trouble him not at all.”

-Martha C. Nussbaum, The Therapy of Desire

In The Therapy of Desire, Martha Nussbaum, one of the most brilliant thinkers I’ve ever read, examines the medical model of philosophy, based on the work of famous Epicureans, Skeptics, and Stoics, all of whom prized the kind of philosophy concerned with real beneficial effects out there in the world, the kind which improved the lives of real people in real-time, instead of the more academic philosophy practiced today.

No stuffy, ivory-tower philosophy in this book. It’s about examining what we really want in life, how we can adjust our desires to better fit what we say that we want in life, and about developing the intelligence and insight to make sure we want the right things, in the right amounts, at the right time.

Essentially, the thinkers she discusses believe that any philosophy that doesn’t alleviate human suffering isn’t worthy of the name. Same as medicine which doesn’t cure what’s wrong with the body should never be called medicine.

Nussbaum also speaks about death quite often in the book, and The Therapy of Desire actually helped change my opinion in this area.

I was reading Antifragile by Nassim Taleb and I thought he was crazy for not wanting to live forever. And while I still absolutely, positively love being alive (I can’t repeat this enough: I do not waste a single minute of my one and only life and neither should you), I can accept Nussbaum’s - and Taleb’s - viewpoint that death is a “making way for others” that sets limits to our existence, within which all our highest values are given expression.

If no one ever died, facing death would not be courageous, our personal relationships would lose some of their poignancy, and our projects would seem hollow. I’m still struggling with this question myself, and I’m certainly nowhere near done living.

I also sympathize with Albert Camus when he said in Resistance, Rebellion, and Death that he is “against this universe, where children suffer and die.” Likewise, I’m not willing to suffer the death of children without fighting back against it, hard; but death, as a necessity and constituent of life itself, does have its place.

This book also put into words something that I’ve often felt previously, namely that the value of each individual human life is infinite.

The implication, of course, is that there is nothing that any of us have to “do” in order to become worthy of unconditional positive regard (in Rogerian terms) and nothing that we have to “become” in order to be persons of absolute value in the universe.

Get This Book on Amazon: Peace of Mind

“Are you not ashamed of yourself, you who gaze upon riches with astonished admiration? Look upon the universe: you will see the gods quite bare of property, and possessing nothing though they give everything.

Do you think that this man who has stripped himself of all fortuitous accessories is a pauper, or one like to the immortal gods?”

-Seneca, Peace of Mind

There's not a single person on earth who can be said to have had an "easy life" (we all encounter difficulties, suffer losses, get sick, and eventually have to face our own mortality), but Lucius Annaeus Seneca is uniquely qualified to teach us about how to claim tranquility of mind because he's been through it all.

Seneca is one of the most influential Roman Stoic philosophers, and although he became tremendously wealthy during his lifetime, he was exiled from the Empire twice (once to Egypt as a young man, and then later to Corsica), came up against many of the same kinds of challenges we all face in our lives, and was eventually ordered to commit suicide by the psychopathic dictator, Emperor Nero, whom Seneca tutored from a very young age.

Seneca had to learn early on that the world just isn't fair: good intentions don't always lead to good outcomes, people who claim to love you will turn their backs on you when it's convenient for them to do so, great achievements often go unrecognized, and then we die at the end.

Luckily for us, it was also around the time of his exile to Corsica that he started writing, and for thousands of years, people of all ages, abilities, and temperaments have come to Seneca's works for wise, soothing, sage advice about how to take the worst the world has to throw at them and still rise to their feet again afterward.

Peace of Mind (De Tranquillitate Animi) is a dialogue written during the years 49 to 62 A.D. concerning the state of mind of Seneca's friend Serenus and how to cure him of his various mental afflictions - anxiety, fear, worry, pessimism, apathy, unhealthy desires, and despair.

Seneca discusses how we can begin to realize the true value of time and get better at investing ours; how we can bear losses bravely and leave ourselves less exposed to the vicissitudes of fate; why freedom/discipline are inextricably linked, and how there's room for both in a life well lived; and also how to laugh at misfortune and find the good in life, even when those all around us can't stop focusing on the negative.

Inside the mind is where it all begins. That's where the majority of our work can and must be done.

We don't see the world as it is, but as we are. So it makes sense to clean and maintain the "viewing window" through which we experience life, see opportunities, and observe reality.

When we learn how to calm the mind, we realize that we're capable of controlling a lot more that happens in our lives as well. Seneca's beautiful little book can help us do this.

Over the last two thousand years, he's been a close friend to millions, and by reading Peace of Mind and experimenting with his philosophy, he can be ours too.

Get This Book on Amazon: Stillness is the Key

“Always think about what you're really being asked to give. Because the answer is often 'a piece of your life', usually in exchange for something you don't even want."

-Ryan Holiday, Stillness is the Key

If you can tolerate enough boredom, you can achieve pretty much anything.

Almost everything that’s worth achieving isn’t going to be the result of one single exciting event, but rather the sum total (or sometimes, the exponential total) of relatively unexciting actions, repeated over and over and over again until your personal summit is reached.

Clearly, there’s a lot more to stillness than boredom, and indeed, whenever such a wide range of societies, belief systems, and successful individuals all converge on one idea as being of singular importance - in this case, stillness - then you know that it’s important and that you overlook its significance at your peril.

Through the stories of people like Confucius, Seneca, Marcus Aurelius, Thich Nhat Hanh, Nietzsche, Fred Rogers, Anne Frank, Winston Churchill - and on and on - Ryan Holiday’s book will show you that stillness isn’t just “sitting still,” or silence, but a superpower that will lead directly to self-mastery, discipline, focus, achievement, and, indirectly, to personal fulfillment.

You’ll learn how to become like a deep lake, capable of cultivating stillness and serenity, while the waves crash and break above you on the surface.

While the rest of the world is like a tiny sailboat being thrashed about in a storm, you’ll be as solid as the ocean floor.

Get This Book on Amazon: Happy

“Given the importance we tend to ascribe to how we come across to other people, it is astonishing that we are so hostile to feedback.”

-Derren Brown, Happy

If you had planned the greatest vacation you could possibly imagine, but you were informed that you would forget everything immediately upon your return, would you even go?

Isn’t it the memories that we create in the process of living that make everything worthwhile? I mean, at the end of our lives, what do we have left?

In Happy, one of the best happiness books I’ve ever read, Derren Brown points out that the “experiencing” self is different from the “remembering” self, a psychological fact supported by research conducted by the Nobel Prize-winning psychologist Daniel Kahneman, Amos Tversky, and others.

What this means is that we’d all be far better served by stuffing our lives with the very best memories possible, than trying to fit in as much temporary pleasure as we can. The pleasure will fade, but the happy memories will make us happy forever.

There’s just so much to this book, and it took me completely by surprise. It was digitally pushed into my hands by a friend who demanded that I read it at once, and, because this friend had never steered me wrong before, I looked past the fact that the book was written by a British mentalist I had never heard of, and I dived right in.

It didn’t take me long before I encountered passages that have stayed with me ever since.

For instance, I now feel quite strongly the truth of the statement that under the same psychological conditions, we would behave much the same as anyone else.

We can never step outside of our own psychological conditioning and find out what it’s like to be driven by the same internal forces as other people. I can’t somehow “renounce” my happy childhood and come to understand, viscerally, why someone who was abandoned by their father acted the way they did.

Their motivations and psychological constitution are completely foreign to me.

This in itself has made me (slightly) more patient, more accommodating, and quicker to forgive. We are all still responsible for our actions, of course, but we are island universes, almost completely unknowable to others.

There’s a healthy dose of Stoic philosophy delivered within the pages of Happy, and if you’re familiar with this happiness-facilitating philosophy, you’ll know that it touches on all these issues and more.

Stoicism has a lot to say about happiness, and it’s certainly informed this book in all sorts of ways. It’s everywhere in his thinking, and that’s a good thing. But Stoicism is about more than happiness. It’s a defense against all the threats to our happiness that abound.

The book’s also surprisingly funny; it isn’t a “serious” book, and it definitely had me laughing in places. The subject matter is serious of course, but Derren Brown doesn’t take himself “seriously.” He’s not serious, but rather sincere. Your “remembering” self will be glad you read this book.

Get This Book on Amazon: How to Think Like a Roman Emperor

“From the moment we’re born we’re constantly dying, not only with each stage of life but also one day at a time. Our bodies are no longer the ones to which our mothers gave birth, as Marcus put it. Nobody is the same person he was yesterday. Realizing this makes it easier to let go: we can no more hold on to life than grasp the waters of a rushing stream.”

-Donald Robertson, How to Think Like a Roman Emperor

This is one of the better modern Stoicism books, almost like a philosophical biography of Roman Emperor Marcus Aurelius, and I came away with a ton of insight into what his actual life was like - details that I rarely see mentioned anywhere else.

More generally, How to Think Like a Roman Emperor is a book detailing the basic tenets of Stoicism, taught through the personal history of, arguably, the most famous Stoic: Marcus.

He was the “final” Stoic philosopher of the ancient world, and his famous book, Meditations, is one of the most-read classics of all time. And for great reason!

Robertson’s book gives you a vivid picture of what Marcus’s actual life was like, what misfortunes he had to endure, and the hardships that came to test his willpower, patience, and resolve.

At the end of the day, Stoicism is meant to be used. It’s meant to help you enjoy and find peace in this life, rather than speculate about the existence of some other one.

Marcus Aurelius is so widely-read today partly because his troubles are so close to our own. The names and faces are different, sure, but he had to deal with rude people too; hostile people, deadly diseases and threats, war and chaos.

He had to confront his own mortality and that of his friends and family. He had to run the whole freakin’ Roman Empire FFS, and his shining example proves that human beings do in fact possess the power to overcome all of that and more.

Get This Book on Amazon: Enchiridion

“Freedom is attained not by obtaining that which you desire, but by removing the desire.”

-Epictetus

Epictetus has always been one of my favorite Stoic philosophers, and his “Handbook,” also known as Enchiridion, is one of the foundational texts of that philosophy. It’s basically required reading for those of us who want to defend ourselves against any adversity we may face, while also remaining open to all the good that life has to offer as well.

Epictetus himself was born a slave in about 55 C.E., in the eastern part of the Roman Empire. He was crippled too, after having been beaten by his master as a small child. After being freed, he established a prominent school of Stoic philosophy, and became one of the most influential teachers from that time period.

You’ll notice parallels between his teaching and the philosophies of people like holocaust survivor Viktor Frankl, who realized that we can’t control what happens to us - we can only choose how we respond. Things will happen to you that…just suck. That’s unavoidable, and nobody makes it through life without experiencing those things.

Maybe (hopefully) you won’t be forced to endure a concentration camp, or be sold into slavery, but misfortune and adversity are common features of human existence.

They’re standing in our path, regardless of how much we may wish things were different, and when they occur, it’s almost as if life is asking us what our answer is going to be. In Epictetus’s case, he chose to “control the controllables,” and to leave the rest to Fortune.

Contrary to what many people assume, Stoics didn’t resign themselves to a life of suffering and hardship - they seized joy where it was available to them, and savored the good times while they lasted, even though they realized those good times wouldn’t last forever.

They couldn’t control the waves, but they could learn to surf. They couldn’t control the length of their lives, but they could influence their depth, and one power they did retain was the power not to let tomorrow’s sadness darken today’s joy.

Get This Book on Amazon: Letters From a Stoic

“What man can you show me who places any value on his time, who reckons the worth of each day, who understands that he is dying daily? For we are mistaken when we look forward to death; the major portion of death has already passed. Whatever years be behind us are in death's hands.”

-Seneca, Letters from a Stoic

Seneca was one of the richest, most powerful people in ancient Rome, and yet he didn’t make it out alive either.

Even while he was alive, his riches didn’t protect him from psychopathic predators, hardship, and death. But Stoicism did, and Seneca became one of that philosophy’s most famous practitioners.

Incidentally, Seneca was the tutor of the sadistic Emperor Nero, and while he tried to teach him some of what it meant to be a good person, Nero ended up ordering that Seneca commit suicide by drinking poison, after the Emperor came to believe that he had been caught up in an assassination plot.

The Stoic principles Seneca taught didn’t penetrate Nero’s consciousness so much, but they were preserved in this series of letters, which reads like a diary or manual of philosophical meditations. Hopefully we can assimilate them better than Nero did!