The (Very) Best Books I Read In 2021

The 2022 Daily Stoic New Year New You Challenge is open for registration! Join me in this year’s challenge—a set of 21 actionable challenges, presented one per day, built around the best wisdom in Stoic philosophy.

I read for a lot of reasons. I read for self-improvement. I read for entertainment. I read to make sense of this crazy world we’re living in. And I read professionally—as a writer, if I’m not reading, I can’t do my job. 

Every year, I try to narrow down all the books I have read and recommended in this email list down to just a handful of the best. The kind of books where if they were the only books I’d read that year, I’d still feel like it was an awesome year of reading. (You can check out the best of lists I did in 2020 (video), 2019, 2018, 2017, 2016, 2015, 2014, 2013, 2012 and 2011.)

The only difference between this year and past years is now I’m the actual owner of a bookstore (read about that here) and I have the extra benefit of having handed these books to people in real life and been able to see how much they helped them too. I promise you—you can’t go wrong with any of these.


Meditations (Annotated Edition, translation Robin Waterfield) by Marcus Aurelius

The fact that Marcus Aurelius was writing during the Antonine plague, that he may well have died of the Antonine plague created a different way for me to see and understand what Marcus was writing about. When he says “you could leave life right now. Let that determine what you do and say and think”—he was talking about that in a time when you really could leave life right now. When he talks about how there’s two kinds of plagues: the plague that can take your life and the plague that can destroy your character—he was talking about the things that we’re seeing in the world, that we saw on a daily basis in 2021. He was writing about a fracturing Rome, a contentious Rome when people were at each other’s throats, when things looked uncertain, when an empire looked like it was in decline. So I got a lot, as always, out of reading Meditations (the Gregory Hays translation), which I keep by my bedside table (here’s what mine looks like these days). But I was VERY excited this year because a new edition has come out, a fully annotated edition by Robin Waterfield, where for almost every passage, Robin provides the necessary context, gives insight into what Marcus was referencing, draws connections to other passages, etc. If you have not read Meditations, Robin’s translation might be the one to start with. I also did a two-hour interview with Robin, which you can listen to on the Daily Stoic podcast (Part 1, Part 2). But whichever translation you go with, the amazing thing about reading Marcus is, year after year, he feels both incredibly timely and incredibly timeless. There’s a reason this book has endured now for almost twenty centuries. 

How The Word is Passed: A Reckoning with the History of Slavery Across America by Clint Smith

We are going through a racial reckoning across the globe. There’s a lot of people that are trying to capitalize on this. People who want us to be divided. People who don’t understand their history. There’s, of course, people who want to stick their heads in the sand about this too, choosing to ignore the history that challenges them or makes them uncomfortable. My understanding of America’s history of racism and slavery comes from a deep study and reading of great minds like Frederick Douglass, Booker T. Washington, and Malcolm X. Last year, I re-read Ellison’s Invisible Man and was profoundly impacted by Taylor Branch’s epic three-part series on Martin Luther King Jr.—truly life-changing for me. But if I could get everyone to read one book to understand the legacy of racial divisions in this country, How The Word Is Passed might be that book. Clint goes and visits the most controversial monuments, plantations, slave pens, markers or moments in American history—from Monticello to the Whitney plantation to Confederate battlefields and cemeteries—and he explores what they mean, how they came to exist, the lies we’ve been told (or told ourselves about them). As it happens, my book store’s building in Bastrop, Texas, dates to the Reconstruction period and is down the street from a particularly odious Confederate statue. Bastrop is actually a town that voted against the secession. But then in the early 1900s, they put up a monument that was designed to celebrate, as one observer said, “the noble white-souled Southland.” And one of the things I’ve been active in is exploring why it’s there and what its actual history is— not the propaganda that it was designed to represent. And when I went down and spoke in front of the Texas historical commission about removing the statue (you can watch that clip here), Clint’s book influenced what I said. I also interviewed Clint on the Daily Stoic podcast. Put your political predispositions aside, put your fatigue with or outrage about the issue aside either way, and read this book. It hit me very hard, and it’s changed how I think about a lot of things. I think it will do the same for you.

The Choice: Embrace the Possible by Dr. Edith Eger

Dr. Edith Eger is a complete hero of mine. At 16-years-old, she’s sent to Auschwitz. And how does this not break a person? How do they survive? How do they endure the unendurable? And how do they emerge from this, not just not broken, but cheerful and happy and of service to other people? The last thing Dr. Eger’s mother said to her before she was sent to the gas chambers was that very Stoic idea: even when we find ourselves in horrendous situations, we can always choose how we respond to them, who we’re going to be inside of them, what we’re going to hold onto inside of them. Dr. Eger quotes the one and only Dr. Viktor Frankl, who she later studied under, “Everything can be taken from a man but one thing: the last of the human freedoms — to choose one’s attitude in any given set of circumstances, to choose one’s own way.” It was this idea that allowed Dr. Eger to not only endure unimaginable suffering, but to find meaning in it. She went on to become a psychologist and survives to this day, still seeing patients and helping people overcome trauma. I had the incredible honor of interviewing Dr. Eger and the joy and energy of this woman, this 93-year-old Holocaust survivor, was incredible (you can watch our interview here). Of course, another incredible must-read in this category is Frankl’s Man’s Search For Meaning. It’s one of my favorite books—one of the greatest works of philosophy ever produced. I wrote an article this year for The Economist about an idea in this book. The idea that while the Statue of Liberty is wonderful and beautiful and inspiring, there needs to be a corresponding statue on the west coast: the Statue of Responsibility. You can read that piece here. And then, mind-blowingly, a delightful gift from the heavens: there was a new book from Frankl this year. How? A set of never-before-published lectures and essays was discovered and published with the incredible title, Yes to Life: In Spite of Everything (with a nice introduction from Daniel Goleman). And really, I think that’s what Dr. Eger did, that’s what Victor Frankl did, that’s what Marcus Aurelius did in the depths of the Antonine Plague and throughout what was an incredibly difficult and painful life—they said yes to life, in spite of everything. The world is hard, the world is unfair, the world can be horrendous—and certainly 2021 illustrated that in so many ways—but we say yes. We make the best of it. We choose our response to those conditions. It’s the last of human freedoms.

Indian Givers: How Native Americans Transformed the World by Jack Weatherford

I have raved before about Weatherford’s book on Genghis Khan (which I used in Ego is the Enemy), but I didn’t know this book existed until I saw it mentioned in Sebastian Junger’s Freedom. Then at the ranger station in Big Bend State Park in June, I saw the book in the gift store. It’s not the most politically correct title, I will grant you that, but this book is INCREDIBLE! It’s about the First Peoples, Native Americans, the people who were here first (in North and South America) and how our civilization has been shaped by their insights, by their ideas, by their innovations—all of which most of us completely take for granted. It’s very rare that I read a book where there is nothing in it that I at least hadn’t heard about before, but that’s what I felt was happening on page after page of this book. Weatherford talks about their breakthroughs in agriculture, their breakthroughs in building, their breakthroughs in hunting, animal husbandry, all these things that you didn’t know about. For instance, Benjamin Franklin gets the idea of a joining of all of the different colonies together from the Iroquois Confederacy at that time. How crazy is that? The idea behind the innovation that we in America take credit for actually belongs to the people who were here first. I sure didn’t hear about that in school…Anyway, Weatherford is a master of making poorly understood (or misunderstood) cultures inspiring and relatable. Read this book for sure


I can’t leave it at just four books. I’ve always loved the “daily read” format, I’ve recommended some of my favorites here before, I’ve been lucky enough to publish one of my own, and this year I was even luckier to have been able to help Robert Greene bring The Daily Laws into existence. People ask me all the time, Where should I start with Robert Greene? This book is where (also we have a bunch of signed copies of his other books in the store too). I loved Martha: The Life and Work of Martha Graham by Agnes de Mille. My rule is that the older the biography, the better. New biographies tend to be trendy, they tend to be politically correct, they tend to focus less on what makes the person and more on a bunch of facts and details that don’t really matter. Martha is an in-depth exploration of Graham’s inspiration, of her excellence, of her practicing, of her obsession with craft. Next—I’m not a huge boxing fan, but I loved Victory Over Myself, the autobiography of Floyd Patterson—the first heavyweight champion to lose the belt and then win it back again, a civil rights activist, and someone who comes across as just a real stand-up human being. Reading Victory Over Myself then reminded me of another boxing book and another favorite, The Harder They Fall by Budd Schulberg. I’d read it at least two other times. The way I remembered it, when I read it the first time, I decided to quit my job in marketing, write my tell all book about it and become a better person. But as I re-read it, I went back to check when I actually bought it…it was in 2008. I stayed at my job for THREE MORE YEARS. I guess life does imitate fiction and growth is always more gradual than we’d like. As the Stoics talk about, it’s not enough to know what’s right, it’s not enough to talk about what’s right—ultimately, you have to do what’s right. Which brings me to my last recommendation. This year I put out Courage is Calling, which I think is my best piece of writing but also, it’s about exactly what Schulberg talks about. Courage isn’t just running into a burning building or fighting it out on the battlefield. It’s the courage to make that lifestyle change, to speak up about something that you know is right, to get involved, to do the hard thing, to do the unconventional thing. That’s what Courage is Calling is about. 

Children’s Books

And as far as kid’s books go, we read quite a few that really stuck with us. Her Right Foot, The Boy, the Mole, the Fox and the Horse, Outside, Inside, and What Does It Mean to Be an American? This was our second year of reading A Poem For Every Day of the Year by Allie Esiri. And it was one night as we were getting ready for bed that my oldest asked me to tell him the story of Marcus Aurelius. This is something I had been thinking about for a long time because a lot of people ask me how they should teach Stoicism to their kids. I started to tell my son a story that we came to call, The Boy Who Would Be King

You can pick up copies of many of the books recommended above at The Painted Porch*, Amazon, your local independent bookstore. But it doesn’t matter to me how you get these books, I just care that you read them, that you put the time into reading. And if you want some advice on how to be a better reader, how to really dig in and get the most out of the books you read, check out my video on how I break down books, take notes to remember everything I read, and use what I read in my own writing. 

*If you do buy online from The Painted Porch, your books will be packed and shipped by us here in Bastrop, Texas! Just remember, we’re a small shop…be patient and kind.

Written by Ryan Holiday
Ryan Holiday is the bestselling author of Trust Me, I’m Lying, The Obstacle Is The Way, Ego Is The Enemy, and other books about marketing, culture, and the human condition. His work has been translated into thirty languages and has appeared everywhere from the Columbia Journalism Review to Fast Company. His company, Brass Check, has advised companies such as Google, TASER, and Complex, as well as Grammy Award winning musicians and some of the biggest authors in the world. He lives in Austin, Texas.