This is a piece from The Obstacle is the Way, which is $1.99 on Amazon right now as part of Kindle’s Daily Deal.

By age twelve, Theodore Roosevelt had spent almost every day of his short life struggling with horrible asthma. Despite his privileged birth, his life hung in a precarious balance—the attacks were an almost nightly near-death experience. Tall, gangly, and frail, the slightest exertion would upset the entire balance and leave him bedridden for weeks.

One day his father came into his room and delivered a message that would change the young boy’s life: “Theodore, you have the mind but haven’t got the body. I’m giving you the tools to make your body. It’s going to be hard drudgery and I think you have the determination to go through with it.”

You’d think that would be lost on a child, especially a fragile one born into great wealth and status. But according to Roosevelt’s younger sister, who witnessed the conversation, it wasn’t. His response, using what would become his trademark cheerful grit, was to look at his father and say with determination: “I’ll make my body.”

At the gym that his father built on the second-floor porch, young Roosevelt proceeded to work out feverishly every day for the next five years, slowly building muscle and strengthening his upper body against his weak lungs and for the future. By his early twenties the battle against asthma was essentially over, he’d worked—almost literally—that weakness out of his body.

That gym work prepared a physically weak but smart young boy for the uniquely challenging course on which the nation and the world were about to embark. It was the beginning of his preparation for and fulfillment of what he would call “the Strenuous Life.”

And for Roosevelt, life threw a lot at him: He lost a wife and his mother in rapid succession, he faced powerful, entrenched political enemies who despised his progressive agenda, was dealt defeat in elections, the nation was embroiled in foreign wars, and he survived nearly fatal assassination attempts. But he was equipped for it all because of his early training and because he kept at it every single day.

In short, the obstacle was the way. Those obstacles made him who he was, and prepared him for everything that lay ahead.

What about you? Could you actually handle yourself if things suddenly got worse?

We take weakness for granted. We assume that the way we’re born is the way we simply are, that our disadvantages are permanent. And then we atrophy from there.

That’s not necessarily the best recipe for the difficulties of life.

Not everyone accepts their bad start in life. They remake their bodies and their lives with activities and exercise. They prepare themselves for the hard road. Do they hope they never have to walk it? Sure. But they are prepared for it in any case.

Are you?

Nobody is born with a steel backbone. We have to forge that ourselves.

We craft our spiritual strength through physical exercise, and our physical hardiness through mental practice (mens sana in corpore sano—sound mind in a strong body).

This approach goes back to the ancient philosophers. Every bit of the philosophy they developed was intended to reshape, prepare, and fortify them for the challenges to come. Many saw themselves as mental athletes—after all, the brain is a muscle like any other active tissue. It can be built up and toned through the right exercises. Over time, their muscle memory grew to the point that they could intuitively respond to every situation. Especially obstacles.

It is said of the Jews, deprived of a stable homeland for so long, their temples destroyed, and their communities in the Diaspora, that they were forced to rebuild not physically but within their minds. The temple became a metaphysical one, located independently in the mind of every believer. Each one—wherever they’d been dispersed around the world, whatever persecution or hardship they faced—could draw upon it for strength and security.

Consider the line from the Haggadah: “In every generation a person is obligated to view himself as if he were the one who went out of Egypt.”

During Passover Seder, the menu is bitter herbs and unleavened bread—the “bread of affliction.” Why? In some ways, this taps into the fortitude that sustained the community for generations. The ritual not only celebrates and honors Jewish traditions, but it prompts those partaking in the feast to visualize and possess the strength that has kept them going.

This is strikingly similar to what the Stoics called the Inner Citadel, that fortress inside of us that no external adversity can ever break down. An important caveat is that we are not born with such a structure; it must be built and actively reinforced. During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on it. We protect our inner fortress so it may protect us.

To Roosevelt, life was like an arena and he was a gladiator. In order to survive, he needed to be strong, resilient, fearless, ready for anything. And he was willing to risk great personal harm and expend massive amounts of energy to develop that hardiness.

You’ll have far better luck toughening yourself up than you ever will trying to take the teeth out of a world that is—at best—indifferent to your existence. Whether we were born weak like Roosevelt or we are currently experiencing good times, we should always prepare for things to get tough. In our own way, in our own fight, we are all in the same position Roosevelt was in.

No one is born a gladiator. No one is born with an Inner Citadel. If we’re going to succeed in achieving our goals despite the obstacles that may come, this strength in will must be built.

To be great at something takes practice. Obstacles and adversity are no different. Though it would be easier to sit back and enjoy a cushy modern life, the upside of preparation is that we’re not disposed to lose all of it—least of all our heads—when someone or something suddenly messes with our plans.

It’s almost a cliché at this point, but the observation that the way to strengthen an arch is to put weight on it—because it binds the stones together, and only with tension does it hold weight—is a great metaphor.

The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us. We don’t need to take our weaknesses for granted.

Are you okay being alone? Are you strong enough to go a few more rounds if it comes to that? Are you comfortable with challenges? Does uncertainty bother you? How does pressure feel?

Because these things will happen to you. No one knows when or how, but their appearance is certain. And life will demand an answer. You chose this for yourself, a life of doing things. Now you better be prepared for what it entails.

It’s your armor plating. It doesn’t make you invincible, but it helps prepare you for when fortune shifts…and it always does.

***

The Obstacle is the Way by Ryan Holiday is $1.99 on Amazon right now for a very limited time. If you want to check it out, or give it as a gift, it’ll never be cheaper than that.

You can also check out our brand new The Obstacle Is The Way pendant, as well as The Obstacle is the Way medallion which is inspired by the same insights from Marcus Aurelius and is awesome for carrying with you everywhere you go.

Writing gets all the attention and all the glamor.

Young aspiring writers love the story of Jack Kerouac, who supposedly wrote On the Road in a three-week drug-fueled blitz. What they know less about is the six years he spent editing and refining it until it was finally ready.

There’s a similar blind spot in all the creative fields. We listen to artists like Adele, who is famous for titling her albums after the age she was when they were made, and then we hear 25, but are too distracted by the fact that it sold 3.38 million copies in its first week to realize that it actually came out when she was 27. We gloss right over the discrepancy. As creatives, we don’t want to ask why it took two years longer than expected, because the answer might be as difficult to hear as the creative process can be to complete.

In Adele’s case? It was because her producer, Rick Rubin, had all but rejected her first submission of the album. “I don’t believe you,” he said after listening to it. There wasn’t enough heart in it. That undefinable, unquantifiable thing that made her first two albums, 19 and 21, so transcendently great simply wasn’t there. It took Adele two years longer to get the album to a place where Rubin believed her. And where she did too.

As a culture, we love flashes of inspiration and we love finished products. We have little interest and little understanding, however, of what goes on in between—of the essentialness of editing and improving and tweaking until whatever we are creating is just right.

But all the greats loved that space. That’s where they lived. That’s where they were most alive.

And that’s where you have to get comfortable as well, to create something of meaning and lasting value.

Why?

The famous Hemingway line on writing:

“The first draft of anything is shit.”

Although creators often dream of a world where no one can tell them what to do and where they get to release everything they make, this fantasy would actually be a nightmare. Because our first effort is rarely good enough. We are too close to our work to see it objectively. And whether we like it or not, the obstacles we jump through as part of the publishing and production processes are what make the work better.

Every creative medium has its own version of the editing process.

Authors submit their manuscript to an editor. There is no The Sun Also Rises or The Great Gatsby without Max Perkins.

Screenwriters attach producers with whom they develop a project. There is no Donnie Darko or Get Out without Sean McKittrick.

Musicians have an engineer, and a producer finishes an album with them (it’s also later mastered). There is no Nevermind or Siamese Dream without the legendary Butch Vig.

Even athletes watch hours of film of their own performance—under the unrelenting analysis of their coaches—before game day. There are not two Michael Jordan three-peats with the Chicago Bulls or the Kobe-Shaq three-peat with the Lakers without Phil Jackson.

All of this is there to take a crappy first draft—a middling first effort—and hone it into something usable. Something brilliant.

Another example: In 1956, a young writer named Harper Lee was given a year’s salary by her wealthy friends Michael and Joy Brown to spend the next twelve months writing the novel she had long put off. The Brown’s have long been considered the heroes behind To Kill A Mockingbird. But really, we know now, that the true hero was Tay Hohoff, the editor at J. B. Lippincott Company to whom Lee sent her manuscript in 1957.

Because as nice and receptive as Hohoff was to the book, she made it clear that, in her opinion, this book would require significant reworking before being published. In Tay’s words, the book was “more a series of anecdotes than a fully conceived novel.” Presumably, Lee’s intention had been to create a full novel, and we can assume she thought she had done so when she delivered the manuscript to her editor. Yet here she was, being told by someone she trusted that she may have failed.

So much in the history of art and culture hinges on moments like this. Faced with soul-crushing feedback or rejection, how does the creator respond? With petulance and anger? With open-mindedness and interest? With obsequiousness and desperation? Or careful consideration that parses the signal from the noise?

It is the creator’s choice at this critical juncture that determines so much—whether the project dies right there, whether it is changed beyond recognition by committee, or whether it is transformed from a decent first attempt into a masterpiece.

Fortunately for all of us, Harper Lee was wise enough to listen. Over the course of several rewrites that took more than two years—effectively producing an entirely new cast of characters and a new plot, while retaining her unique and essential perspective—Lee created To Kill a Mockingbird, one of the great works of American literature.

To the public, Mockingbird had been perfect all along. It’s so pure. So innocent. So heartfelt. That has to be natural right? It wasn’t until 2015, when that first draft was published as Go Set a Watchman, that we realized the truth: Without an editor, without a lot of hard work and a lot of editing, history may have never heard of Harper Lee. She wouldn’t have deserved for us to.

This is true for all the geniuses and masterpieces. Even the ones that came down as stream of consciousness. As a Kerouac scholar remarked on the 50th anniversary of On The Road:

“Kerouac cultivated this myth that he was this spontaneous prose man, and that everything that he ever put down was never changed, and that’s not true. He was really a supreme craftsman, and devoted to writing and the writing process.”

What are the chances that your prototype is perfect the first time? WD-40 is named after the forty attempts it took its creators to nail the working formula. The Great Gatsby was rejected several times. The script for Back To The Future was rejected over 40 times. The script for the Best Picture winner, American Beauty, was revised twice in consultation with the director, Sam Mendes, before it went out to actors, and then when Mendes got into the editing process of the film itself he ended up cutting together something nearly 180 degrees removed from what he thought he was making during principal photography. Precisely zero of my ten books were immediately accepted by my publisher—and they were right to kick them back at me. In being forced to go back to the manuscript, I got the books to where they needed to be. I know that now, but at the time it was infuriating to be told, “It’s not quite there yet.”*

As infuriating as it may be, we must be rational and fair about our own work. This is difficult considering our conflict of interest— which is to say, the ultimate conflict of interest: We made it. The way to balance that conflict is to bring in people who are objective. Ask yourself: What are the chances that I’m right and everyone else in the world is wrong? We’ll be better off at least considering why other people have concerns, because the reality is, the truth is almost always somewhere in the middle.

Every project needs to go through this process. Whether it’s with an editor or a producer or a partner or a group of beta users or just through your own relentless perfectionism—whatever form it takes is up to you. But getting outside voices is crucial. The fact is, most people are so terrified of what an outside voice might say that they forgo opportunities to improve what they are making. Remember: Getting feedback requires humility. It demands that you subordinate your thoughts about your project and your love for it and entertain the idea that someone else might have a valuable thing or two to add.

Nobody creates flawless first drafts. And nobody creates better second drafts without the intervention of someone else.

Nobody.

Not even you.

This was originally published on Writing Routines.

•••

If you’re looking for a way to keep this maxim in mind, Writing Routines recently released a print version of Hemingway’s quote:

“The First Draft of Anything Is Shit”

Learn more here.

Every year, I try to narrow down all the books I have recommended and read for 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.

I know that people are busy, and we don’t always have time to read as much as we like. Nothing wrong with that (though if you want to read more—don’t look for shortcuts—make more time!). What matters is that when you do read, you pick the right books.

This list is now 125,000+ 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. But…before I get into my favorites this year, I wanted to tell you about something I’m really excited about for 2019. We are kicking the year off with a 14 Day—New Year, New You—Challenge for Daily Stoic. The one we did in October was awesome, and I had an amazing time doing it alongside thousands of you. This one is going to be even better and actually has some reading related challenges that I think you’ll love. Give it a look.

Also if you want signed or personalized copies of my books as Xmas gifts this year, BookPeople.com is offering those, and we also have some cool gift ideas in the Daily Stoic Store!

***

A Calendar of Wisdom: Daily Thoughts To Nourish the Soul by Leo Tolstoy 

I read one page of this book every single day in 2018. It’s basically a collection of Tolstoy’s favorite passages from the ancient and classic texts, with excellent supplements from his own considerable wisdom. Each day draws on Chinese, Jewish, Stoic, Christian, Indian and Arabic sources (he quotes everyone from Emerson to Marcus Aurelius to Lao-Tzu) and manages to give good, actionable advice from all of these differing schools. It’s no wonder the Communists banned and suppressed this book, because it challenges everything they were trying to deny about human nature and the human experience. But luckily it did survive and has finally been translated into English. This book should be much, much, more popular and I promise your mornings will be improved if you start them with it.

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

This was definitely the best business/leadership book I read this year. It was recommended to me by the lacrosse player Paul Rabil when I did his podcast. What a book! It proves that we have really missed what makes great teams and organizations work. It’s not star players, it’s not even how much they can spend–it’s whether they have great captains. Athletes like Bill Cartwright on the Chicago Bulls, Carla Overbeck on the US Women’s Soccer team, Yogi Berra of the New York Yankees and Jack Lambert of the Pittsburgh Steelers were not by any means the most famous or the most talented players, but they were the glue that held the team together. Walker’s chapter on “carrying the water” had some great insights re: Ego is the Enemy and I think this incredibly well-written book should be studied by anyone trying to build a great organization (or trying to find a role for themselves inside one). Related, and lesser known recommendation: Everyone should read Sadaharu Oh’s autobiography, A Zen Way of Baseball. He’s the greatest home run hitter of all time, a Zen master, and basically nobody outside of Japan knows who he is. Brilliant and beautiful book. 

Victoria: The Queen: An Intimate Biography of the Woman Who Ruled an Empire by Julia Baird and Clementine: The Life of Mrs. Winston Churchill by Sonia Purnell 

I read so many biographies this year and these two biographies of two extraordinary British women were two of my absolute favorites. I knew nothing about Queen Victoria but Julia Baird does an amazing job of making her accessible and interesting–and captures just what life was like for a woman in the 19th century, even if she was a queen! I knew a lot more about Churchill but Sonia Purnell’s examination of Winston’s better half was truly revelatory. (Churchill said the best decision he ever made in his life was marrying Clementine and this book make it clear just how many times she saved his ass). Both of these books are entertaining, insightful and teach a ton about the times the subjects lived in. Any other biographies I liked this year? Thank you for asking! I was riveted (and appalled) by Jeff Benedict and Armen Keteyian’s biography of Tiger Woods and probably talked to more people about about this book than anything else I read this year. I got around to reading Walter Isaacson’s biography of Da Vinci just in time to go see The Last Supper in Milan. Truly excellent book about one of history’s all time greats. Evan Thomas Being Nixon: A Man Divided is one of the best books I’ve ever read about a politician. It’s worth reading whatever country you live in and whatever your political beliefs are. A final book I’d add this collection would be Rosanne Cash’s memoir, Composed. I heard about it from Steven Pressfield and it’s excellent. 

Honorary Mentions: Robert Greene’s The Laws of Human Nature came out this year and it was well-worth the half-decade wait since Mastery. He is a living treasure and everyone should read this new one. I think the best book I’ve ever written, Conspiracy, came out this year as well (The New York Times said it was genius, so that counts for something…). Camus’ The Fall was the best novel I read this year. I really enjoyed the new series of translations that Princeton University Press has done of Cicero and Epictetus and Seneca. They are worth reading for sure. Kate Fagan’s book What Made Maddy Run? was one of the books I most recommended to sports coaches and parents I know. Finally, I made a concerted effort to read more eastern philosophy this year and really got a lot out of Readings in Classical Chinese Philosophy by Philip J. Ivanhoe which is a collection of most of the classic Confucian and Taoist writings. After that I read The Bhagavad Gita, which is something I wasn’t ready for before, but glad to finally understand. 

Anyway, that’s a lot of books I just mentioned and they should keep you plenty busy. However, if you want more, you can check out the best of lists I did in 2017, 2016, 2015, 2014, 2013, 2012 and 2011.

And of course, you can get a lot of these books on Scribd, which is basically unlimited ebooks and audiobooks (and a New York Times subscription) all in one app for one low monthly price. Worth trying for sure.