My latest book, Wisdom Takes Work, is officially out and you can get a copy wherever you buy books! Thank you to everyone who has picked up a copy. The support has been incredible—and honestly, a little overwhelming. Our small team here at The Painted Porch is working hard to get every order out the door as fast as we can. If you’re still waiting on yours, we really appreciate your patience. Believe me… I have been working on this series for 6 years—I can’t wait for you to read the new book!

In the summer of 2019, my wife and I took our two sons for a hike in the Lost Pines Forest in Bastrop, Texas. 

It was a Saturday or a Sunday. 

I had a bunch of articles to write, but I put it aside and decided to spend some time outside with the kids in the shade of the prehistoric loblolly forest about thirty minutes from our house. 

It was a lovely afternoon, despite the heat. I always love Lost Pines because it’s a freak of nature. The tall prehistoric loblolly pine trees appear here in the middle of Texas, hundreds of miles further east than most of their counterparts. Much of the forest still shows scars from two 2011 wildfires that burned tens of thousands of acres—one of them the worst in Texas history—only adding to the mystique and making parts feel like a haunted elephant graveyard. 

As we wrapped up the hike and took the kids to the playground, suddenly, it hit me. It was a feeling that creative people experience from time to time. You’re in the middle of not working–you’re in the shower or your drifting off to sleep or you’re in the middle of sweeping the floor–and boom, you get hit with an idea. I have run many hundreds of miles in Lost Pines so it was a familiar feeling—I’ve sold business problems and writing problems and personal problems on the trails there. 

As I was carrying my son in the backpack, my mind had drifted briefly to the fact that my book Stillness is the Key would soon be released and it would mark the end of what had become a three-book trilogy. What would I tackle next?, I thought. This was 2019. The political situation was a mess. There were wildfires, earthquakes, wars dragging on, terrorist attacks. There was chaos, upheaval, and uncertainty. “A book about courage would be cool,” popped into my head. I shared the idea with my wife. We talked it over along the trail, and by the time we were loading the kids in the car, an idea for one book had become an idea for a series on the four virtues, starting with courage!

And like that, my next creative mountain had been laid out in front of me. 

I’ve been thinking about this story lately because here I am, six years later, coming to the end of that series, as the fourth and final book, Wisdom Takes Work, came out last week.

There was a period a couple of years ago where I didn’t think I would be here having completed the series. It was around the halfway mark, working on the second book in the series, Discipline is Destiny, and I hit a wall. 

Coming up with the idea for a book—or in this case, a series—is a fun, creative act. Actually creating those books is a work of excruciating manual labor, sitting in a chair, grinding out each consecutive sentence—a process not measured in hours or days, but months and years. It’s a marathon of endurance, cognitive and physical.

For me, in the last decade, I have run not just a couple of these marathons but twelve of them, back to back to back. That’s roughly 2.5 million words across titles I’ve published, articles I’ve written, and the daily emails that I produced in the same period. 

During that time, there was a destabilizing, devastating global pandemic. There were fires, floods, and freezes. Demagogues and wars. Market crashes and inflation. Technological disruption. My kids growing up. My wife and I opening and running a small town bookstore.

So I was tired. Just really tired. 

I’m not someone inclined to believe in divine intervention. But I needed help . . .

On a sweltering-hot day in Texas, I was sitting at my workroom table in my office above the bookstore. The air conditioner wasn’t working and I wasn’t sure if we could afford another one for the building. It was my 34th birthday. Sweating, exhausted, and on the verge of a crisis of confidence—that I had the wrong topic, I didn’t have the material, and contemplating whether to call my publisher and ask for a delay—I went through boxes that contained thousands of note cards of research. As a whole, they overwhelmed me—what they contained, the way they might fit together to produce a book, seemed impossible to comprehend. I reached out and grabbed one.

It had just two dozen words scrawled in red Sharpie. When was it written? Why had I written it? What had prompted me? All I know is what it said.

Trust the process. Keep doing my cards. When I check them in June—if I have done my work—there will be a book there.

It wasn’t exactly a miracle . . . but defying space and time, I had traveled from the past into the future to deliver a reminder of self-discipline.

And guess what? It was exactly what I needed.

It didn’t save me from the work, of course, but from myself. From giving up. From abandoning the system and process that had served me so well on all those books and articles and emails. In one of the best passages in Meditations, Marcus Aurelius, almost certainly in the depths of some personal crisis of faith, reminds himself to “Love the discipline you know, and let it support you.”

That’s what my note said to do.

I listened.

I began showing up at the office earlier each day to work with my material. Card after card, I sorted them into tiny little piles. Looking for connections, for threads I could follow, for the key that would unlock the book.

Instead of worrying, I used the calm and mild light of the philosophy I have written about in my books. I went for long walks when I got stuck. I tried to follow my routine. I tuned out distraction. I focused. I also sat—just sat—and thought.

I’d love to be able to tell you that shortly after this the book just clicked. But that’s not how writing, or life, works. What actually happened was slower, more iterative, but also in the end, just as transformative. 

As I walked that long hallway of doubt and despair, as I kept doing my cards, light began to creep in. Lou Gehrig and Angela Merkel stepped forward from the shadows. After nearly four thousand pages of biographies, Queen Elizabeth entered as a portrait of temperament. Napoleon, Alexander the Great, Julius Caesar, and King George IV jumped out as cautionary tales, stunning examples of self-inflicted destruction. One character after another slowly, painstakingly, chapter by chapter, became discernable. 

The book was there, as my note promised me. Now I had to write it.

While a book requires many, many hours of work, these hours come in rather small increments. If I get to the office at eight thirty, I could be done writing by eleven. Just a couple hours is all it takes. Just a couple crappy pages a day, as one old writing rule puts it. The discipline of writing is about showing up. No delays, no procrastination, no digital distractions. Just writing.

The seasons changed. World events raged and spun as they always do. Opportunities, distractions, temptations, they did what they do too—popping up, pinging, nagging, seducing. 

Day after day, I kept after it. I trusted the process. I loved the discipline I knew. I let it support me. 

As I finished the book, I was still tired. Every writer is tired when they get to the end of a book. Yet, I also felt wonderful. I thought it was to date some of my best writing, but what I was proudest of is who I was while I wrote it. A less disciplined me, a younger me, would have been wrecked by that period where it felt like the book might not come together. I would have acted out. I would have been consumed. But the work had been working on me—as I worked from home on the final pages of Discipline, my five-year-old looked up from his art project and said, “I’m sorry you lost your job writing books, Dad.” Apparently things had been so much less crazy and my boundaries had been so much better that he thought I wasn’t working anymore! 

But I was, of course. I was in the process. Doing my cards. Trusting the discipline I knew would lead to the next book, Right Thing Right Now, and the final one, Wisdom Takes Work. 

As a result, here I am—having read over 500 books of research, made 10,000 note cards, published 300,000 words (with tens of thousands of additional words cut) and 1,400 pages—drawing the series to a close. 

When Edward Gibbon finished ​The Decline and Fall of the Roman Empire​, he noted his sadness at taking “everlasting leave of an old and agreeable companion.”

I don’t feel that way, though, because of everything I learned during these past six years spent working on the series, the clearest lesson of all is that virtue isn’t something you take leave of. It’s not something you ever fully possess. It’s not something you commit to just for a little while, but for a lifetime.

There’s still a long way to go, but I’m proud of the progress I’ve made. I’m proud of what I have put to the page in each of the four books. And I’m proud of how I’ve improved both as a writer and a person through it all. I am calmer. I am quieter. I argue less. I get upset less. I admit I am wrong more often. I’m a little wiser, a little more disciplined, just, and courageous than I was on that hike in the summer of 2019.

I close the virtues series, but the ideas are still working on me. I am doing my best to live up to them. To be more community-minded. To be braver, stronger, kinder, wiser. 

Day by day. Page by page. Struggle by struggle. 

I hope you do the same.

…and now I go onto my next project. 

If you haven’t checked out Wisdom Takes Work, it would mean so much to me if you could. It came out last Tuesday. Here’s me talking about it on The Daily Show and on The Breakfast Club.

We still have some signed first-edition copies of Wisdom Takes Work left—and will be extending our preorder bonuses for folks who buy the book this week. Bonuses include cut chapters and the annotated bibliography with all purchases, or a signed manuscript and even dinner with me if you buy more copies.

If you’re interested, grab your copy now before it’s too late.

My new book, Wisdom Takes Work, comes out in 6 DAYS!  If you’ve gotten anything out of my writing over the years, it would mean the world if you preorder a copy. Preorders are the single best way to support an author and help a book get off the ground. To make it worth your while, I’ve put together a bunch of bonuses—a signed page from the original manuscript, bonus chapters, an annotated bibliography, and more. Just head to ​dailystoic.com/wisdom before October 21st to claim your bonuses.

There I was at 19 years old, sitting across from the great Robert Greene at The Alcove in Los Feliz.

He was talking about all the trouble he was having finding a good research assistant. 

I had to restrain myself from jumping over the table.

This was literally my dream job. 

Fortunately, before I leapt out of my chair, Robert asked if I might have any interest in giving it a shot. 

Thus started for me what Robert calls in Mastery, The Apprenticeship Phase.

It didn’t start with anything glamorous. In the days before AI or even decent software, I spent hours transcribing interviews he had done for his book The 50th Law. I read obscure books he didn’t want to waste time on. I found articles. I worked on his website. I went to libraries and scanned pages. I went through old archives. I tracked people down.

And in between, I asked questions. I listened. I watched. I absorbed his research and note card system, which I continue to use to this day.

Obviously he was paying me, but I always considered having access to him—being able to ask these questions—my actual compensation. The feedback wasn’t always fun, but what would he have normally charged someone as a consultant? How many people would have killed to be able to call him or email him about anything?

When I say I was his apprentice, I don’t mean it like, “Oh, I was his intern for a few months.” I did this for close to 7 years, even after I became the director of marketing at American Apparel. I was even doing it even after I had gotten my own book deal and was working on my first books. 

Why? 

Because this is how it works. 

As the great Jack London writes in his novel Martin Eden, “no matter how peculiarly constituted a man may be for blacksmithing, I never  heard of one becoming a blacksmith without first serving his apprenticeship.”  

In Wisdom Takes Work—which there are just 6 days left to preorder!—there are multiple chapters on the art of cultivating these mentors and teachers because there is no one who is able to reach their potential totally alone. There is no one who can learn everything they need to learn by trial and error. Wisdom is not a solitary pursuit. It is often a collective effort.

For thousands of years, this is how trades—and life—were taught. Not in a classroom with hundreds of other students, but attached to a professional, who taught, largely by example, until the student was ready to head out on their own. There are some things, the tennis great Billie Jean King would say of her time  training under Alice Marble, an eighteen-​time Grand Slam Champion, “you can only learn from someone who’s been the best in the world.” Or at least, someone who is world class.

It was from Robert that I learned everything—literally everything—about being a writer. He taught me how to write a book, how to think about books, how to research them, how to market them, how to work with a publisher. He fundamentally taught me, from beginning to end, how the entire process works. In addition to telling me what to do, he showed me how a real pro does the job. 

We have to find the people who can teach us and open ourselves to learning from them. Whatever stage of life we’re in, there is someone who knows more than us, who has been through more than us, who can open doors for us.  

We are a product of our teachers and our mentors. 

There would be no Plato without Socrates. There would be no Aristotle without Plato. There would be no Alexander without Aristotle. There would be no Marcus Aurelius without Rusticus or Epictetus or Antoninus. There would be no Zeno without Crates, and thus there would be no Stoicism without Crates. 

Do you know what Crates’s nickname was in ancient Athens? He was known as “the door-opener.” Because that’s what great mentors and teachers do: They open doors to worlds we didn’t even know existed. They invite us into things we wouldn’t have discovered on our own. They help us see possibilities we’d otherwise stay blind to. 

How do you find these door-openers? How do you attract their attention? How do you make yourself worth their while?

You have to show yourself as somebody with the hunger to learn and excel. You have to show yourself as somebody who listens. Somebody who is curious. Somebody who is worth teaching. Somebody who is coachable.  

Mentors give us books to read. They give us problems to solve. They give us riddles to chew on. They provide an example that inspires or even shames…and sometimes cautions. 

The process is not always fun. It will often be painful. As Epictetus would tell his students, having modeled himself on his mentor Musonius, “The philosopher’s lecture hall is a hospital. You shouldn’t walk out of it feeling pleasure, but pain, for you weren’t well when you entered.” 

Valuable things are rarely free. An apprenticeship is one of them. 

But it’s also priceless. 

I wouldn’t be here without it. 

There’s no way I can repay Robert for his kindness and his patience and his generosity. But as I explain in the “Grow a Coaching Tree” chapter in Right Thing, Right Now (the third book in the Virtue Series), as well as in the “Be a Teacher” chapter in Wisdom Takes Work, the only thing we can do is pay that forward. The next step is to become a teacher, to help mentor someone else. 

Because we learn as we teach. 

Because we carry debts from those who helped us—debts that can only be discharged through helping others.

And because, at the end of your career and your life, you’ll be prouder of what you helped others accomplish than what you achieved yourself. 

But only if you put the work in now…working as hard to open doors for others as you work to open doors for yourself.  

***

For the past six years I’ve been lavishing all my working hours on the Stoic Virtues series and I can honestly say Wisdom Takes Work, the fourth and final book in the series, is the culmination of my life’s work.

There are just SIX DAYS left to pre-order Wisdom Takes Work! 

Each time I release a book, I like to do a run of preorder bonuses like signed and numbered first editions, early access to the introduction, bonus chapters, and even an invite to a philosophy dinner at my bookstore, The Painted Porch. 

Just head to ​dailystoic.com/wisdom before October 21st to claim your bonuses.

My new book, Wisdom Takes Work, comes out in 13 DAYS! If you’ve gotten anything out of my writing over the years, it would mean the world if you preorder a copy. Preorders are the single best way to support an author and help a book get off the ground. To make it worth your while, I’ve put together a bunch of bonuses—signed and numbered first editions, a signed page from the original manuscript, bonus chapters, an annotated bibliography, and more. Just head to ​dailystoic.com/wisdom before October 21st to claim your bonuses.

I thought I knew a lot about Lincoln. 

I’ve read biographies—an embarrassing amount of them honestly. I’ve watched documentaries. I’ve interviewed scholars. I’ve traveled to many of the sights. I’ve read many of his favorite books. I’ve immersed myself in the world he lived in. I once stood transfixed, for hours, in front of Krzysztof Wodiczko’s art piece, which projected the faces and experiences of American veterans on the face of Lincoln’s statue in Union Square  Park in New York.

I’ve even written about him quite a bit in my books. 

So when I sat down to put together what was intended to be Part III of Wisdom Takes Work, I thought I was set. 

It turns out I wasn’t even close. 

I was stuck and I could not find the words. That might seem like writer’s block but it wasn’t—because writer’s block doesn’t exist. What is real is lacking material and that’s what I was facing. 

So I got to work. 

I read Michael Gerhardt’s 496-page book on Lincoln’s mentors. 

I read Hay and Nicolay. 

I read Doris Kearns Goodwin’s 944-page Team of Rivals. 

Still, there was more to know. 

So I read David S. Reynolds’s 1088-page Abe, David Herbert Donald’s 720-page Lincoln, and Garry Wills’s Pulitzer Prize–winning book specifically about the Gettysburg Address (Wills’s book has many more pages than the address has words). 

I spoke with the documentarian Ken Burns about him, and Doris too. 

I went back through the books I’d already read (William Lee Miller, especially, but also Harold Holzer, Joshua Wolf Shenk, and Carl Sandburg). 

I read Lincoln’s own writings, his letters and his speeches. 

I reviewed my pictures from trips to Gettysburg, Antietam, and Ford’s Theater. 

I went, multiple times in the course of writing the book, and looked up at the Lincoln Memorial. 

In the end, I spent hundreds of hours reading thousands and thousands of pages on the man. Here’s what that looks like in physical terms. 

Basically, what I was doing was a deep dive. Fittingly, Lincoln’s own education was itself a kind of lifelong series of self-directed deep dives. He got his start in law, for instance, when he met a lawyer named John T. Stuart, who allowed Lincoln to borrow some of his law books. “If you wish to be a lawyer,” Lincoln would later tell a young man, “attach no consequence to the place you are in, or the person you are with; but get books, sit down anywhere, and go to reading for yourself. That will make a lawyer of you quicker than any other way.”

His campaign against slavery, too, began by going deep. “He searched through the dusty volumes of congressional proceedings in the State library,” William Herndon, Lincoln’s law partner, recalled, “and dug deeply into political history.” His way, Herndon observed, was to dig up a question by the roots and dry it out by the fires of the mind, until he could see it for what it was.

Do you know what Lincoln did after the Civil War broke out? He broke out an old habit, which he’d had since his time in Washington as a congressman: He called for books from the Library of Congress, reading everything he could about strategy and tactics, including books published by his own generals. He was, by the end of the war, according to General W. F Smith, “the superior of his generals in his comprehension of the effect of strategic movements and the proper method of following up victories to their legitimate conclusions.”

Nowhere was this ability to see things plainly more evident than in the Gettysburg Address, which was just 271 words long. You might think such a short speech was easy to write, in fact, it was the descendent of a decade-plus-long deep dive into language, elocution, rhetoric, history, law, politics and the founding ideals of the nation—a word he repeated in the speech five times. It was an expression of the work Lincoln did to get to the “nub” of a subject, as his law partner said. As Wills writes in Lincoln at Gettysburg: The Words that Remade America, Lincoln was able to, as a result of his masterful understanding of the issues and opportunity at hand, to effectively redefine and refound the nation in a single speech, in a way that two and a half years of war had not been able to. 

Going deep in order to get to the nub of subjects—this is a skill you need to have. Whether you are an author, a politician, a lawyer, entrepreneur, scientist, educator, parent—it doesn’t matter you have to be able to pursue an idea, a question, a thread of curiosity until you’ve wrapped your head completely around it.

In Right Thing Right Now, I spend a lot of time talking about the abolitionist Thomas Clarkson, who like Lincoln was able to strike a defining blow against slavery. Obviously this is what we’re talking about when we talk about justice. But how did he do it? Clarkson knew slavery was wrong. He even wrote a convincing essay on it.. But he soon realized that if he was going to do something about it, he would really have to understand slavery—as a business, a logistical enterprise, and a set of cultural assumptions passed down for thousands of years to justify it. So he immersed himself in the abolitionist movement, meeting and learning from the earliest activists, reformers, and freed slaves. He visited slave ships. He would recall that the almost uninhabitable quarters, the chains and grates, filled him “with melancholy and horror,” kindling, he said, “a fire of indignation.” But now his anger was fueled by facts, and he wanted more. He spoke to everyone he could find who had been to Africa, recording their accounts in his notebooks. He scoured records at the Custom House, poring over muster rolls, ship logs, trial transcripts, and insurance files.

Often falling asleep over paperwork, surrounded by his research, Clarkson persisted for years. By the end, no one knew more about the slave trade—he was more informed than many traders and investors themselves, since so much of what they did depended on deliberate ignorance.

You can’t solve a problem you don’t understand. You can’t lead a field you haven’t immersed yourself in. You must go down the rabbit hole. You must go deep. You must swarm the topic. 

This has been my approach to pretty much everything I’ve done since dropping out of college. It’s how I figured out how to be a writer. It’s how I figured out how to be a researcher. It’s how I figured out how to be a parent. It’s how I figured out how to run a bookstore. Indeed, my whole life has been built on deep dives.

If our goal is to get not just smarter or more knowledgeable, but wiser, we cannot be content to learn in half measures. We must go as deep as we possibly can. We don’t just read a book on a topic. We have to read everything we can find on it. We don’t just ask a question or find an expert. We have to find every expert we can and ask them every question they’re willing to answer. We don’t just look at what’s there. We have to explore the remotest corners, every facet, from every angle. We have to hear from people we agree with and from people we disagree with. We have to go out and get real experience.

As an old man Marcus Aurelius would reflect on the most important lesson he had learned from his philosophy teacher Rusticus: “to read attentively—not to be satisfied with ‘just getting the gist’ of things.” Go “directly to the seat of knowledge,” he said. Immerse yourself in the craft, business, sport, or profession. Seek out tutors and mentors and peers. Travel. Observe. Ask questions. Go way beyond the “gist.”

The great biographer David McCullough talked about swarming the subjects he wrote about—reading their diaries, their favorite books, biographies of their heroes, newspapers from their time, and, most importantly, spending time in the places they had spent time. “I believe strongly,” he once said, “that terrain, landscape, the physical environment is not just important in understanding someone or something—it’s elemental. Therefore, I go to where things happened.”

The jazz legend Miles Davis didn’t just go down to the  club and listen to music. “I would go to the library and borrow  scores by all those great composers, like Stravinsky, Alban  Berg, Prokofiev. I wanted to see what was going on in all of  music,” he explained. All of music. Old stuff. New stuff. The  greats. The weirdos. “Knowledge is freedom and ignorance is  slavery,” he said, “and I just couldn’t believe someone could be  that close to freedom and not take advantage of it.” 

The Wright brothers didn’t discover flight through a single epiphany but through countless hours watching birds. “We couldn’t help but thinking they were just a pair of poor nuts,” one Kitty Hawk resident recalled. “They’d stand on the beach for hours, watching the gulls flying, soaring, dipping.” They even studied how paper fell and floated to the ground, again and again.

Wilbur’s notebooks are filled with drawings of birds, notes on flight techniques across species, and how weather affected flight. They include sketches of wind-tunnel tests and designs. Others had observed birds, but no one had gone so deep—or spent so much time—studying the mechanics of flight and wings.

To capture the progression from ignorance to knowledge to wisdom, McCullough used the example of the pilot’s cockpit. You can get a pretty good understanding from someone describing what a cockpit is. An even better understanding from reading about cockpits. An even better understanding from looking at pictures. An even better understanding from watching videos. An even better understanding from sitting in a cockpit. And an even better understanding from flying a plane.

This is our job. To make things clear. To get to the nub of things. To find what is important and discard the rest. To go deep. To swarm. 

This, of course, takes time. 

It takes curiosity.

It takes patience and persistence. 

Most of all, as I put in the title of the ​new book, it takes work.

***

For the past six years I’ve been going deep on the four virtues, and I can honestly say Wisdom Takes Work, the fourth and final book in the Stoic Virtues series, is the culmination of my life’s work.

The book comes out October 21st, but it would mean the world to me if you could preorder the book from ​dailystoic.com/wisdom. Preordering a book is the number one thing you can do to support an author as they get a book off the ground. It’s how publishers determine how many copies to print, whether other bookstores will carry it, and where the book will land on the bestseller list.

To make ordering it early worth your while, I put together a bunch of bonuses like signed and numbered first editions, a signed page from the original manuscript, bonus chapters, an annotated bibliography, and a bunch of other stuff. Just head to ​dailystoic.com/wisdom before October 21st to claim your bonuses.