Before the best books of 2022 — The 2023 Daily Stoic New Year New You Challenge is open for registration! For the last four years, the New Year New You Challenge—a set of 21 actionable challenges, presented one per day, built around the best wisdom in Stoic philosophy—has helped thousands of people get the best out of themselves. Don’t wait to better yourself. Don’t wait to demand more of yourself. Become the better you. The new you.

I am very blessed, I always say, to get to read for a living. If I don’t read, I can’t write, it’s that simple. But of course, that’s not the only reason I do it. I read to live.

It’s how I relax. It’s how I make sense of what’s happening in the world. It’s how I get better as a parent. It’s how I visit different worlds and travel through time. One of the nice things about the last few years was there was plenty of time for reading. But in 2022, I had less white space on the calendar. There were speaking engagements and a book tour and TV appearances. My oldest started school. I even took our family to Disneyland. Protecting my reading time took more discipline this year–and one of my resolutions is to be even more disciplined about it in 2023.

At the end of 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 2021, 2020, 2019, 2018, 2017, 2016, 2015, 2014, 2013, 2012 and 2011.)

My reading list is now ~250,000 people, which means I hear pretty quickly when a recommendation has landed well. I promise you—you can’t go wrong with any of these.

Caste: The Origins of Our Discontents by Isabel Wilkerson

There’s a great analogy at the center of this book that I think works as both an approach to life and to learning. In order for a doctor to cure you of your ills, Wilkerson writes, you have to give them a medical history. If because you’re ashamed of something or in denial of something, and you hold back, you’re not helping anyone. In fact, you’re hurting yourself. Our own history–in America or anywhere in the world–is not a list of the things we’re proud of. It is a list of the things that happened. In order to get better, to improve, to get closer to ‘a more perfect union,’ we have to gather and put up for review an unflinching history. It’s not always fun…but it’s the only way. A few years ago, I read and loved Wilkerson’s other book Warmth of Other Suns—a beautiful, painful and eye-opening look at the Great Migration through biographical sketches of Blacks who left the Jim Crow South for a chance at a better life in California, in Chicago, in New York City. Her newer book, Caste, is less a historical analysis and more of a philosophical and sociological book, but equally powerful. “All men are created equal” might be the goal of the American experiment, but no medical history is complete without an honest look at the racial hierarchy that not only existed for hundreds of years but was enforced with violence and cruelty at first and then more passively and systemically after that. Caste is a human folly, a human evil–but one we can address by facing it. A few related books I read that I can’t recommend highly enough: Last year I raved about Tom Ricks’ book First Principles, which is about the deep influence the Greek and Roman philosophers had on the American founders (here are his first two appearances on the Daily Stoic podcast about it). His new book Waging a Good War (which he talked about in his most recent appearance on the podcast) is about what he calls the greatest war in American history led by what he describes as the greatest generation in American history—the leaders of the Civil Rights Movement. It was Martin Luther King Jr. who came to Washington in 1963 to ‘cash a check,’ to redeem that promise first made in the Declaration of Independence. Influenced by Gandhi’s work with the untouchables, King came to understand the role that caste played in American society, and his I Have a Dream Speech was a direct attack on it. I was also deeply moved, in some cases to tears, by David Halberstam’s book, The Children. You can listen to my interviews this year with Ernest Green, one of the Little Rock Nine, and Eric Holder, who wrote an important book on voting rights.

Plain Speaking: An Oral Biography of Harry S. Truman by Merle Miller

When he was a young man, Charles Bukowski came across an all but forgotten novel in the Los Angeles Public Library called Ask the Dust (my favorite novel. Please read it!!!). It was like finding gold in the city dump, he said. Well, nothing gets me more excited than discovering long-forgotten or out of print classics. I think I found one in this biography of Harry S. Truman. Of course, the David McCullough bio of Truman is a classic (and we carry it at The Painted Porch for a reason), but this one…this one is one of the best leadership books I have ever read. I actually bumped into it when I was trying to track down a passage about how Truman read and marked up a copy of Meditations (check out the leatherbound edition of my favorite translation). Originally conceived as a television project, what emerged is just an absolute masterclass in self-education, decency, loyalty, patriotism, making tough decisions and leading a good life. Read it–it’s worth every penny of however much Amazon charges for used copies. Or pay homage to Truman’s love of libraries (he read every book in his local library as a kid) and check out a copy. We built the Daily Stoic reading course around his famous quote: “Not all readers are leaders but all leaders are readers.”

The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness by Morgan Housel

This year began with a booming economy, and is ending in recession. Crypto has crashed. The real estate market is not so hot. If you’re looking to navigate the whipsawing, unpredictable nature of the global economy as an individual who hopes to plan (and be secure) for the future, I think this book is a great one. It’s filled with great stories–like the kind I try to tell in my books–that teach big lessons. There’s no better way to learn in my eyes…I had a great conversation with Morgan on the podcast, which you might also like. But speaking of podcasts and financial advice, I have LOVED–like LOVED–Ramit Sethi’s podcast this year which focuses on couples and their financial issues. It’s riveting and super educational. I’ve learned a ton. Here’s my interview with Ramit in that regard.

Nomadland: Surviving America in the Twenty-First Century by Jessica Bruder

Over the last couple years, my family and I took many road trips in a small camper trailer we bought in the early days of the pandemic. We drove across Texas and New Mexico and Arizona and up the middle of California. We drove across Louisiana and Mississippi and Alabama and Florida. As we spent time at campgrounds and RV parks, I often wondered who the other people staying there were–people who did not seem to be just passing through like us. So I grabbed this book, which is about a whole hidden segment of the working population. People often in their late fifties and sixties, who live in vans and RVs, traveling not unlike the nomads of the past, looking for seasonal work–often in backbreaking Amazon warehouses–trying to make ends meet and enjoy what is supposed to be the best years of their lives. I don’t mean to make the book sound like some sociological study. It is also just great narrative journalism (good enough that it was also made into an award-winning movie). It was strange though, as I read the book, there was this part of me that tried to take issue with each of the character’s stories. Like where their own decisions had held them back, where their mistakes had caused all this misfortune and struggle. What I was doing, I came to see, was trying to find reasons that I didn’t have to care. In truth, society has failed these people (not that they always made great decisions), but a better and more accessible American dream would be more forgiving, sturdier and rewarding. Anyway, if you want to understand some of our broken and angry political system, this is a good book to read. If you are in tech or in the modern economy, in a nice house in a nice city…read this book. Discover how another part of the country lives. Try to care. Try to understand it.

Outdoor Kids in an Inside World: Getting Your Family Out of the House and Radically Engaged with Nature by Steven Rinella

I first met Steve Rinella at a coffee shop in New York City many, many years ago. I’ve recently gotten reacquainted with him because my 5-year-old son is obsessed with his videos on YouTube (you can listen to him at the beginning of my podcast with Steven). His new book—which was perfectly timed for our recent family trip to Big Bend—is about how to cultivate a love for outdoors in a time where cultivating a love for outdoors is both more important and harder to do than ever. It’s funny that a YouTube video would kick this all off, but the book is not some anti-screen screed. It’s about encouraging curiosity and interest, and cultivating resiliency and self-sufficiency. We try to learn about places we’re going, discover new hobbies, find cool stuff to check out. I loved this book and we wrote a number of Daily Dad emails about it which I think you might like (try here and here and here and if you’re not signed up for it, please do!)

More…

I can’t leave it at just seven books. As you’ve seen in the list this year, I published two books myself this year, The Girl Who Would Be Free and Discipline is Destiny. Before I start any book project, I take a few hours and re-read The War of Art by Steven Pressfield, maybe the greatest book ever written on the creative process. But in 2022, I changed it up a little because I got an early copy of Pressfield’s new book, Put Your Ass Where Your Heart Wants to Be. I love the title so much because it’s the perfect advice for nearly every difficult thing. I quite enjoyed Chuck Klosterman’s book The Nineties. I liked Anne Morrow Lindberg’s A Gift From The Sea. David McCullough’s The Night of the Johnstown Flood was terrifying and riveting. Erik Larson’s The Splendid and the Vile was a fascinating look at London during the Blitz…and relevant to what’s happening in Ukraine. Kathrine Kressmann Taylor’s Address Unknown was something I re-read in light of the alarming rise of anti-semitism. And finally, Michael Schur’s How To Be Perfect was a great work of philosophy that I loved this year.

Children’s Books

Of course, I’ll reiterate Steve’s book on raising outdoor kids and if you haven’t read either The Boy Who Would Be King or The Girl Who Would Be Free, I would love for you to check them out. Stoicism is a philosophy I wish I had found earlier…and I wrote these books to help kids do exactly that. My oldest became obsessed with Minecraft this year so we spent a lot of time going through the 6-book series the Minecraft Woodsword Chronicles. They are great books to do a chapter or two of a night. As far as all-out fun kids books, we have returned again and again and again to The Book With No Pictures–my kids think they are pranking me by asking me to read it…of course what they’re actually doing is falling in love with books. Along those lines, we loved I Need a New Butt (there’s a series). For some insane reason some people are trying to ban this book in Texas, but that’s just another reason to buy it (I’ll spoil the ending…he needs a new butt because his has a crack in it.) If you’re trying to raise a reader, Maya Smart (podcast episode here) wrote a great book on exactly that–I think every parent should read Reading for Our Lives. Finally, we’re still loving The Boy, The Horse, The Fox and the Mole, which is absolutely beautiful and a monster bestseller for a reason.

As always, I appreciate you supporting my bookstore, The Painted Porch. Please note that because a lot of the books we sell are backlist titles, there can sometimes be delays in stocking/sourcing. And with that, I hope that you’ll get around to reading whichever of these books catch your eye and that you’ll learn as much as I did. Whether you buy them at The Painted Porch or on Amazon today, or at your nearest independent bookstore six months from now makes no difference to me. I just hope you read!

You’re welcome to email me questions or raise issues for discussion. Better yet, if you know of a good book on a related topic, please pass it along. And as always, if one of these books comes to mean something to you, recommend it to someone else.

I promised myself a long time ago that if I saw a book that interested me I’d never let time or money or anything else prevent me from having it. This means that I treat reading with a certain amount of respect. All I ask, if you decide to email me back, is that you’re not just thinking aloud.

Enjoy these books, treat your education like the job that it is, and let me know if you ever need anything.

All the best,

Ryan

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There are lots of smart people.

There are not a lot of people who can do this smart thing.

The poet John Keats called it “negative capability”—the mental fortitude to be able to entertain multiple contradictory ideas in your head at the same time. Or as F. Scott Fitzgerald famously wrote, “The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function. One should, for example, be able to see that things are hopeless, yet be determined to make them otherwise.”

The world is complicated, ambiguous, paradoxical, and contradictory. To make sense of it, to survive it, one must be able to balance conflicting ideas. To try to force everything into a simple box, or adhere to a simple theory? It just won’t work.

People will sometimes email me, “Ryan, Marcus Aurelius contradicts himself. Sometimes he says to zoom in and other times he says to zoom out.” Or they’ll point out that Seneca’s writings tell us to be aware of the dangers of the future and also never avoid anxiety and worry.” Or that they are confused because Law 3 in Robert Greene’s The 48 Laws of Power is “conceal your intentions” but Law 6 is “court attention at all cost.”

I’ve even gotten this about Discipline is Destiny which of course talks about being strict with yourself…and also not so strict with yourself. Is that a contradiction?

The answer is yes.

The famous lines from Walt Whitman are,

Do I contradict myself?

Very well then I contradict myself,

(I am large, I contain multitudes.)

Yes, Marcus Aurelius contradicts himself. Yes, the Stoics contradict themselves. Yes, Robert Greene’s laws of power contradict each other. Yes, I contradict myself.

Because the world contradicts itself. Because different situations call for different things. Because everything in life depends on context.

Look, even the premise that only a genius can manage negative capability is itself a little contradictory. Because you know who has no problem holding a bunch of conflicting ideas at the same time? Really dumb people!

So negative capability seems to follow the Midwit Meme curve.

So how do you cultivate the kind of negative capability Keats was talking about? Here are some thoughts:

[1] Read widely and from people you disagree with. One of the most surprising parts of Seneca’s writing is how often the avowed Stoic quotes Epicurus, the founder of the rival school, Epicureanism. The reason he was so familiar with Epicurus, Seneca wrote, was not because he was deserting the writings of the Stoics, but because he was reading like a spy in the enemy’s camp. That is, he was deliberately reading and immersing himself into the thinking and the strategies of those he disagreed with. To see if there was anything he could learn. Epicurus’s dictum was that “One sage is no wiser than another.” The Stoics believed this too—that we should actively pursue and engage with anyone who can be a source of wisdom to us, regardless of the school of thought from which that wisdom arose. Because if there is wisdom out there to be had, we’d be wise to avail ourselves of it.

[2] Study deeply. Marcus Aurelius chided himself “not to be satisfied with just getting the gist of it.” Instead, he said, “read attentively.” Go “directly to the seat of knowledge.” Seek out tutors and mentors. Linger, as Seneca said, on a small number of master thinkers, reading and re-reading their work. Go way beyond the “gist.”

[3] Put yourself in rooms where you’re the least knowledgeable person. Observe and learn. Ask questions. That uncomfortable feeling, that defensiveness that you feel when your most deeply held assumptions are challenged? Do it deliberately. Let it humble you. In my own education, I’ve always followed Marcus Aurelius’ rule: “go straight to the seat of intelligence.” He also writes, “Mastery of reading and writing requires a master. Still, more so life.” For me, Robert Greene was and is my master in writing and, more so, in life. Go straight to the sources of knowledge, people who have different perspectives and expertise, people who can help you see things from a new angle and to consider alternative viewpoints. Absorb as much as you can from them.

[4] Understand that timing and context are everything. Confucius was once asked for advice by a student, and in replying essentially urged him to wait and be patient. Later he was asked for advice by another student, and advised that student to not be patient and to solve the problem immediately. An observant third student noticed the seemingly contradictory nature of Confucius’ responses and asked him to explain. Confucius replied, “Ran Qiu is over cautious and so I wished to urge him on. Zilu, on the other hand, is too impetuous, and so I sought to hold him back.” Everybody is different. Every situation is different.

[5] Embrace epistemic humility. Epictetus reminds us that “it’s impossible to learn that which you think you already know.” To the Stoics, particularly Zeno, conceitedness was the primary impediment to wisdom. Because when you’ve always got answers, opinions and ready-made solutions, what you’re not doing is learning. The physicist John Wheeler said that “as our island of knowledge grows, so does the shore of our ignorance.” The point is the more you know the more you realize there is much more to know.

[6] Keep your identity small. This is a rule from the great Paul Graham. His point was that the more you identify with things—being a member of a certain political party, being seen as smart, being seen as someone who drives a fancy car or someone who belongs to this club or that ideology—the harder it is for you to change your mind or entertain new points of view. You want to remain a free agent.

[7] Don’t always have an opinion. It’s possible, Marcus Aurelius said, to not have an opinion. Practice the ability of having absolutely no thoughts about something. You should be able to have multiple ideas you’re working on in your head at one time, as opposed to a bunch of things you have strong opinions about.

[8] Flexibility is key. A colleague of Churchill once observed that Churchill “venerated tradition but ridiculed convention.” The past was important, but it was not a prison. The old ways—what the Romans called the mos maiorum—were important but not to be mistaken as perfect. Plenty of people have been buried in coffins of their own making. Before their time too. Because they couldn’t understand that “the way they’d always done things” wasn’t working anymore. Or that “the way they were raised” wasn’t acceptable anymore. We must cultivate the capacity for change, for flexibility and adaptability. Continuously, constantly.

It’s one of the greatest exchanges between Epictetus and a student. “Tell me what to do!” the student says. Epictetus replied, “you must understand how laughable it is to say, ‘Tell me what to do!’” The student is confused. Epictetus says, “What advice could I possibly give? No, a far better request is, ‘Train my mind to adapt to any circumstance.’ . . . In this way, if circumstances take you off script . . . you won’t be desperate for a new prompting.”

It would be nice if someone could show us exactly what to do in every situation. Indeed, this is what we spend a good portion of our lives doing: preparing for this, studying for that. Saving for or anticipating some arbitrary point in the future. But that’s not life. Life punches us in the face. It destroys our plans.

The Stoics did not seek to have the answer for every question or a plan for every contingency. Yet they’re also not worried. Why? Because they have confidence that they’ll be able to adapt and change with the circumstances. Rooted in the teachings of Epictetus, the United States Navy Vice Admiral and prisoner of war James Stockdale perfectly described this mental attitude when he said that to survive years of imprisonment and torture, he needed a paradoxical combination of optimism and realism. He needed to maintain unwavering faith that he would ultimately prevail, and at the same time, he needed to confront the brutal facts of his current situation. As Fitzgerald put it above, Stockdale needed to “be able to see that things are hopeless yet be determined to make them otherwise.”

Instead of looking for instruction, the Stoic cultivates skills like creativity, independence, self-confidence, ingenuity, and the ability to problem solve. They cultivate negative capability. They cultivate true genius.

In this way, they are resilient instead of rigid.

Gratitude, like forgiveness, is something we pay lip service to but struggle with in practice.

It’s one of those things, as I like to say, that’s simple…but not easy.

Today, Thanksgiving here in America, is a day where we’re supposed to take the time to think about what we’re grateful for. And the candidates are usually pretty obvious: We should be grateful for our families, for our health (especially through a pandemic), that we live in a time of peace (the first Thanksgiving America has not been at war in 21 years), for the food laid out in front of us. All the usual suspects.

I agree, these are important things to recognize and appreciate. It’s also good to have a specific day dedicated to that occasion. So by all means, celebrate.

But what about all the other stuff in the world?

The obstacles. The frustrations. The stresses and difficulties of life. The people that wronged you. The haters. The dilemmas. The bad days.

That too?

Yes, that especially.

The writer Jorge Luis Borges said:

Or as my mentor Robert Greene once told me,

It’s all material.

He means that everything that happens in your life can be turned into something useful, whether it’s your writing, your relationships, or your new startup. You probably wouldn’t have chosen for things to go wrong–just like no one would choose any of those things on the list of current events above–but they came anyway. Now the question is, how are you going to think about them?

Are you going to think about what you don’t like? What you resent or fear or hate? Or are you going to find the good in them, what you can use in them, what you can be grateful for in them?

In the mornings when I sit down to journal, one of the notebooks I write in is a gratitude journal. When I first got it, I would fill the pages with all the stuff I liked about the stuff I liked. But after a time, this came to feel sort of pointless and rather repetitive. Now what I do is try to find ways to express gratitude, not for the things that are easy to be grateful for, but for what is hard.

• Gratitude for that nagging pain in my leg
• Gratitude for that troublesome client
• Gratitude for the challenges of the pandemic
• Gratitude for that delayed flight
• Gratitude for that damage from the storm

Because each one was an opportunity. Because I learned from it. Because it reminded me of what was actually important. Because it’s allowed me to see how lucky I am. Because I became a better person for it.

Every situation has two handles, the Stoics would say. Which one will you grab?

As Cicero explains, “you may say that deaf men miss the pleasure of hearing a lyre-player’s songs. Yes, but they also miss the squeaking of a saw being sharpened, the noise a pig makes when its throat is being cut, the roaring thunder of the sea which prevents other people from sleeping.”

In the chaos and dysfunction of the world, I try to notice where I have been gifted in the latter category than where I have been deprived in the former.

Besides, it’s already happened…what’s the use in getting upset?

“Let us accept it,” Marcus Aurelius wrote to himself in his journal, “as we accept what the doctor prescribes. It may not always be pleasant, but we embrace it —because we want to get well.” He could have been talking about the pandemic of his times, the stresses of his job or the children he had buried. He could have been talking of his own ill-health, the bad weather, or the noise of the city’s streets. We don’t know, we just know that whatever it was, he was trying to find a way to say thank you for it, to be grateful for it. “Convince yourself that everything is the gift of the gods,” Marcus said, “that things are good and always will be.”

Beautiful.

So as you gather around your family and friends this Thanksgiving or Christmas or any other celebration you might partake in, of course, appreciate it and give thanks for all the obvious and bountiful gifts that moment presents. Just make sure that when the moment passes, as you go back to your everyday, ordinary life, that you make gratitude a regular part of it. Again—not simply for what is easy and immediately pleasing. That comes naturally enough, and may even go without saying.

What is in more desperate need of appreciation and perspective are the things you never asked for, the things you worked hard to prevent from happening in the first place. Because that’s where gratitude will make the biggest difference and where we need the most healing.

Whatever it is. However poorly it went. However difficult the last few years have been for you.

Be grateful for it. Give thanks for it. There was good within it.

Write it down. Over and over again.

Until you believe it.