Ryan Holiday Picks 20 Books to Help You Live Better in 2020

A reading list that’s all about what really matters

2020 is already looking rough. On top of all the ordinary stresses that come with 12 months of life on Earth, we’re in a divisive election year, one that’s bound to be filled with bitter fights and deepening fears. So how do we get through it?

Especially in difficult times, I think the goal should be to think more clearly, to be provoked less, to be kinder, to see the bigger picture, and to improve at the things that matter to us.

It’s a lot to take on. But we can start by turning to smart people who might know more than us in these areas — people, some alive today and some from thousands of years ago, who have done hard thinking on hard topics and distilled their wisdom into books. Here are 20 of those books — some new, some old — that will help you live better, be better, and meet the goals that matter for 2020.

Plutarch’s Lives by Plutarch

One of the best ways to learn is by studying the lives of successful people: their flaws, their virtues, their strategies, and their failures. One problem with studying people from the modern era, however, is that everyone and everything has been politicized. Winston Churchill, Elon Musk, Michelle Obama — we are too close to their lives to learn from them dispassionately and with the proper perspective. That’s why I recommend looking way back.

Take some time this year to read Plutarch’s timeless works of complicated, larger-than-life figures — Pericles, Demosthenes, Themistocles, Cicero, Alexander the Great, Caesar, and Fabius — and take in everything that is good and bad about the human condition. Greed, love, pain, hate, success, selflessness, leadership, stupidity — it’s all there. When you realize how similar we are to those who came before us, how history has been and always will be, you’ll learn to dim the noise and hopefully be inspired to make your own mark.

Keep Going: 10 Ways to Stay Creative in Good Times and Bad by Austin Kleon

Like I said, this may be a difficult year for people. It may be hard to focus. Hard to be hopeful. Hard to know what to do. This book is so perfect for the moment we’re in: It’s full of strategies for pushing through despair, chaos, or that looming sense that the world is falling to pieces around us. Austin Kleon doesn’t promise any magical solutions, but he does think that all of us sitting down and getting to work — making good stuffcan add up in a big way.

The Second Mountain: The Quest for a Moral Life by David Brooks

Chasing personal success is the first mountain. But what happens after you get to the top? What happens when you find out, as many of us do, “Oh wait, this is not nearly as satisfying as I thought it would be. All of my problems are still here.” That’s when we begin to look for what David Brooks calls the Second Mountain. No, it’s not just a taller version of the first one. This is the one where we start thinking less about ourselves and more about other people.

“True good fortune,” Marcus Aurelius reminded himself at the height of his power and fame, at the summit of his first mountain, “is good character, good intentions, and good actions.” True good fortune is doing stuff for other people. For your community. For your country. For the world. This book won’t just make you think about your life, it will make you question everything you knew about your life.

The Woman’s Hour: The Great Fight to Win the Vote by Elaine Weiss

No matter what side of the political aisle you’re on, you probably want things to be different, to be better. This is an important book because it shows you what it takes to accomplish that, and just how much resistance you’ll face in trying to make change. We are bad at understanding the battles that have been fought to gain even basic, common-sense progress.

In these chaotic, divisive political times, when the only thing we all seem to agree on is that there’s a lot to be angry about, a book like this is important. It shows how the democratic process actually works, by small, incremental movements that add up to transformative shifts. It shows that what we need — in life, in activism, in sports, in everything — is restraint and resilience and courage, not rage. In 2020, we need less anger and more dedicated, savvy activists like the ones who helped pass the 19th Amendment.

My Side of the Mountain by Jean Craighead George

A friend of mine helped me build a tree fort this summer and left this book for me to read to my three-year-old. The recent “free-range kids” movement is a reasonable reaction to the way adults have trampled on childhood. Kids need to be outside. They need to learn how to be independent. How to go on adventures. How to tap into the innate part of themselves that likes to build, to live off the land, to be one with nature. This is a beautiful book about the value of the outdoors, self-sufficiency, companionship, and how much we take for granted. It has just enough pictures to keep a young kid’s attention, and it’s filled with action, adventure, lessons, and interesting observations that adults will love, too.

Range: Why Generalists Triumph in a Specialized World by David Epstein

Specialization, as the saying goes, is for insects. The real greats — the people we really admire — are multi-hyphenates. Or at least they were at one point. (People forget that Tom Brady was also drafted by the Montreal Expos baseball team.) While mastery requires real dedication to one thing, before you can make that sort of commitment, you need to have cultivated a range of skills and interests. That’s how you bring a unique voice to whatever you do. I don’t think I would be an interesting writer if I had only trained in writing from childhood; the experiences I’ve had in business, marketing, and researching give me something to say. The more interests we open ourselves up to, the better we’ll be as leaders, employees, and individuals.

How To Keep Your Cool: An Ancient Guide to Anger Management by Seneca

Take a minute to think back over the times you’ve been angry or short-tempered and think, “Has this ever served me well?” The answer is very rarely yes. Anger, as Seneca says, tends to make things worse: “No plague has cost the human race more dear.” This was originally written to be a kind of moderating influence on a young Nero, who Seneca was advising, but it has endured through the centuries as a warning to keep our cool and to not give in to rage or resentment.

Everything is Figureoutable by Marie Forleo

It’s easy to be a defeatist, especially these days, with the cowardice of our politicians and the cruelty of our discourse. We’re all struggling on a personal level in some way, too: We’re trying to fix our marriage or get into college. We’re trying to finish a report for work or build that piece of Ikea furniture. We have a difficult neighbor or want to open our own business. Sometimes we want to throw up our hands and say we quit. This is why Marie Forleo’s mantra “everything is figureoutable” is exactly what we all need. The book lays out the destructive thoughts that arise when we’re learning something new, and helps us view our potential through a different lens.

The Captain Class: A New Theory of Leadership by Sam Walker

At a time when people seem to have no clue what leadership looks like, this book is especially important. The key to strong organizations, strong teams, and strong governments is almost always an unsung hero — not the one in front of the camera, but the one who works behind the scenes to keep everything together and bring out the best in everyone.

In this book, Sam Walker studies athletes like Bill Cartwright on the Chicago Bulls, Carla Overbeck on the U.S. Women’s Soccer team, Yogi Berra of the New York Yankees, and Jack Lambert of the Pittsburgh Steelers. None of these people were the most famous or most talented players on their respective teams, but they were a critical ingredient in their team’s success. I also strongly recommend everyone read Walker’s piece in the Wall Street Journal about Dwight D. Eisenhower, who defined leadership as “the art of getting someone else to do something that you want done because he wants to do it.”

Memoirs of Hadrian by Marguerite Yourcenar

This novel — essentially a faux but deeply realistic memoir of the Emperor Hadrian for the benefit of his successor Marcus Aurelius — is just an utterly beautiful book. Hadrian isn’t exactly a household name to us, or particularly admired by historians, but that’s what makes the novel so impressive. “Our great mistake,” the imagined Hadrian says, “is to try to exact from each person virtues which he does not possess, and to neglect the cultivation of those which he has.” Marguerite Yourcenar manages to find all sorts of powerful, inspiring virtues in Hadrian that he can pass along to Aurelius, and by extension, to us.

The Autobiography of Malcolm X by Malcolm X

In 1946, Malcolm Little went to jail. Looking at a decade behind bars, he faced what Robert Greene calls an “Alive Time or Dead Time” scenario. He could have served his time simply counting the days. Instead, he started reading. He literally copied the dictionary word for word. Every minute he wasn’t in his bunk, he was in the library. That was how Malcolm Little was transformed into Malcolm X, one of the great civil rights leaders of the 20th century. There’s a lot we can learn from his life and his choices.

George Marshall: Defender of the Republic by David Roll

You probably don’t think you want to read a book about George Marshall. That makes sense. In fact, that’s how he would have preferred it. Marshall, who served as Secretary of State and Secretary of Defense under Truman (and won the Nobel Peace Prize for the Marshall Plan) wanted to be the guy behind the scenes: Famously, he turned down $1 million in the 1950s for his memoirs. During a time of political outrage, backstabbing, spotlight coveting, posturing, greed, and ass-covering, it’s good to read about someone who put his mission above all that. As Marshall’s wife later observed, he had ego, self-interest, pride, and ambition like everyone else, but these were “tempered by a sense of humility and selflessness.” It is hugely important that David Roll has brought Marshall into full view in the 21st century because we desperately need more people like him.

Call Sign Chaos: Learning to Lead by General James Mattis

There is a story about Mattis, as a very senior officer, who took over guard duty on Christmas so a soldier could be home with his family. “Know what you will stand for and, more important, what you won’t stand for,” Mattis writes in the book. “State your flat-ass rules and stick to them.” Mattis, who announced his resignation as Secretary of Defense in late 2018, shows restraint rooted in integrity throughout the book: Among other examples, he declines to attack President Trump because of a personal rule against discussing sitting presidents and leaves nameless an officer he had relieved of duty in the Iraq War. The man lives by a code. We need more of that.

The Library Book by Susan Orlean

Some people can just flat-out write. Susan Orlean is one of them. Not every book you read has to be serious. This one — a story of the unprecedented library fire that destroyed millions of books in the Los Angeles Public Library in 1986, and the attempts to catch the arsonist behind it — should be read just for the pure entertainment value. And, of course, for Orlean’s beautiful meditations on the power of books and the magic of libraries.

Ask the Dust by John Fante

This is one of my favorite novels. To me this is just a wonderful book about the perils of ego, the pain of loneliness, the cost of ambition, and the love/hate relationship some of us have with Los Angeles. It was written in 1939, but only began to find its audience as Fante was dying, when it was rediscovered in the Los Angeles Public Library by Charles Bukowski. It’s bonkers to think that the very copy he found likely burned in the fire that Susan Orlean talks about in her book.

President Lincoln: The Duty of a Statesman by William Lee Miller

Last year I recommended Lee’s unique “ethical biography” Lincoln’s Virtues. This year, I am recommending the sequel. Lincoln was a man whose life was defined by enduring and transcending great difficulty. He taught himself to read, braved the wild Mississippi River, learned the law, and worked his way up from poverty into the presidency, where he ended slavery and kept America from permanently tearing itself apart. We must follow Lincoln’s example and adjust to a world that is inherently unpredictable by remaining confident, calm, ready to work regardless of the conditions, and convinced that we can make a difference. This is a book that will give you hope: Sometimes at the right moment, the right leader appears.

The Cost of These Dreams: Sports Stories and Other Serious Business by Wright Thompson

The old joke is that when the gods wish to punish us, they give us everything we’ve ever wanted. Wright Thompson’s book is a beautiful piece of writing about athletes who reach the pinnacle of their sport, but forget that it was a love of the game that got them started — or worse, never once stopped to think about what they really want out of life. This book also dovetails nicely with Brooks’ The Second Mountain.

Philosophy as a Way of Life: Spiritual Exercises from Socrates to Foucault by Pierre Hadot

Philosophy is and has always been an operating system for living, for being a good human being, and for solving the problems of life, like managing our tempers, finding meaning, and figuring out how to think about death. Pierre Hadot one of the most prominent scholars of ancient philosophy, masterfully shows how philosophy can guide us through the real world and our real problems.

Confucius from the Heart: Ancient Wisdom for Today’s World by Yu Dan

One of the great things about reading widely from philosophy is that you discover how much agreement there was between the various schools of thought, whether they overlapped or not. This fascinating, accessible, and wildly popular translation of Confucius can help you understand just why he has been so long admired in the Eastern world. He was brilliant, but he was also a pragmatist. He knew that suffering was inevitable, and that what matters most is how we respond.

Love Wins: A Book About Heaven, Hell, and the Fate of Every Person Who Ever Lived by Rob Bell

I’m agnostic, but I liked this book anyway. Rob Bell is a pastor, and this book is definitely about faith and God and Christianity—which don’t usually appeal to me—but it’s more than that. It’s about the meaning of life and why we should be good people. Bell rejects the idea that there is such a thing as hell. In fact, nowhere in the Bible is there anything close to the hell that believers talk about today — a place where bad people and nonbelievers go after they die to be tortured and punished for their sins for all eternity. Even the word “hell,” which varies from translation to translation, appears only a few times, with different contextual meanings in each case.

So what might Jesus and the Christians have been speaking of when they spoke of hell? Bell’s take: “People choose to live in their own hells all the time. We do it every time we isolate ourselves, give the cold shoulder to someone who has slighted us, every time we hide knives in our words, every time we harden our hearts in defiance of what we know to be the loving, good, and right thing to do.” Let’s remember that.

WWhen I wrapped up my list of books last year, I made one final recommendation that I will repeat this year. Whether you read any of the books above or not — this year or next year — I do think you would be vastly improved by the experience of picking three or four titles that have had a big impact on you in the past and commit to reading them again. Seneca talked about the need to “linger among a limited number of master thinkers, and digest their works, if you would derive ideas which shall win firm hold in your mind.”

And no matter how many times you read a certain book, you never read the exact same book twice because you change from one reading to the next. So this year, go reread To Kill A Mockingbird. Give The Odyssey another chance. Sit with a few chapters from the 48 Laws of Power. See how these books have stood the test of time, and see how your perspective differs from when you read them last.

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’ http://amzn.to/24qKRWR

Sign up for The Forge Daily Tip

By Forge

A quick morning email to help you start each day on the right foot. Take a look.

Check your inbox
Medium sent you an email at to complete your subscription.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store