The following article is an adaption of one of best chapters in my book Conspiracy: A True Story of Power, Sex, and a Billionaire’s Secret Plot to Destroy A Media Empire. The book is out in paperback today and I think is one of my best pieces of writing ever. The New York Times called it “one helluva pageturner” so if you’re looking for something to read this summer, give it a look.

It is easy to confuse strategy and boldness. 

 “Given the same amount of intelligence,” Clausewitz dictum goes, “timidity will do one thousand times more damage in war than audacity.

It was a favored expression of the Roman poet Virgil, for instance, that Fortune favors the bold. 

But the truth is that most difficult ventures and even most stunning victories are as much the result of patience and due diligence than any single, brave stroke. 

For instance in 2012, nearly five years have passed since Peter Thiel had been outed as gay very much against his will by by Gawker Media. It hadn’t taken too long after that Wednesday in December for him to decide that something had to be done, but it had taken four full years since then to conceive of what kind of response might even be possible. Thiel founded and sold PayPal in considerably less time. Gawker itself had gone on to become a company worth hundreds of millions of dollars.

But Thiel, sworn to exact vengeance on the people who he believed had humiliated was not noticeably any closer to his goal. He had made only a single hire, a then-anonymous twenty-something named Mr. A would be tasked with leading Thiel’s conspiracy to destroy Gawker.  

“With patience and resources,” Mr. A would come to say often on his weekly calls with Peter, “we can do almost anything.” Tolstoy had a motto for Field Marshal Mikhail Kutuzov in War and Peace—“Patience and Time.” “There is nothing stronger than those two,” he said, “. . . they will do it all.” In 1812 and in real life, Kutuzov gave Napoleon an abject lesson in the truth of that during a long Russian winter.

Their target, Nick Denton, the founder of Gawker, is not a patient man. Most entrepreneurs aren’t. Most powerful people are not. One of his editors would say of Denton’s approach to stories, “Nick is very much of the mind that you do it now. And the emphasis is to get it out there and be as correct as you can, but don’t let that stand in the way of getting the story out there.” Editorially, Nick Denton wanted to be first—which is a form of power in itself. But this isn’t how Thiel thinks. He would say his favorite chess player was José Raúl Capablanca, and remind himself of the man’s famous dictum: To begin you must study the end. You don’t want to be the first to act, you want to be the last man standing.

How does one do that? Especially against a wily and powerful opponent? 

We can look to Eisenhower in his battles with Joseph McCarthy, then at the height of his power as a demagogue. Though most Americans would come to see Eisenhower as the kindly, friendly “Ike,” they did not realize that beneath that exterior was a cunning strategic mind that knew how to wield power without raising alarms and was, if anything, a patient plodder. Seeing that opposition and publicity were what gave McCarthy his power, he looked for a better opportunity. Eisenhower began to work behind the scenes, directing and pushing for others to limit McCarthy’s power, stripping the man of allies, using his own allies to criticize him, removing opportunities McCarthy would have liked to take advantage of. It’s because of this use of the “hidden hand” that McCarthy never knew that the president was working against him, and so when Eisenhower crushed McCarthy, and crushed him completely using the man’s weaknesses against him, it would be decades before historians could even piece the evidence together.

So the user of special means must scorn the obvious—ignore the conventional wisdom and voices from the sideline. Eisenhower watched as McCarthy attacked his closest friends, pocketing at one point a full- throated defense of George Marshall that he must have wanted to give so badly, because while it might have scored public points against his opponent, it wasn’t the right strategy.

“It’s almost limitless what one could do,” Mr. A said, musing on all the theoretical angles of attack they brainstormed in meetings at Thiel’s house and in late-night phone calls. Given the resources he had to draw on, the limitlessness of the options is nearly true: they could have bribed employees at Gawker to leak information, or hired operatives to ruin the company from the inside. They could have directed hackers to break into Gawker’s email servers. Someone could have followed Nick Denton and, while he dined at Balthazar one morning, stolen his cell phone. A team could have attempted to bug the Gawker offices. You could fund a rival website, operate it at a loss, and slowly eat away at the razor-thin margins of Gawker’s business. Or create a blog that does nothing but report on gossip about Gawker writers—returning the very pressure and scrutiny they’d put on other people. “There are things that were very tempting, an eye for an eye, tooth for a tooth. Retributive justice,” Peter said. “But I think those would’ve ultimately been self-defeating. That’s where you just become that which you hate.” The victory would be pyrrhic, too, easier but at a higher personal cost.

A decision was made to eliminate the strategies that would either be illegal or fall into any one of a number of gray areas. For instance, Thiel could have easily hit Gawker with many meritless cases that he never expected to win in order to bury the company in legal bills, but how effective would that really have been? It’s a brute-force tactic that ignores the strategic value of exploiting your opponent’s fundamental weakness—if one could be found. “There were all these things that you could be tempted to do and it’s not clear they would work any better. So we decided very early on we would only do things that are totally legal, which is a big limitation. But it forced us to think really hard about what to actually do,” says Peter. “We were comfortable taking a very aggressive legal posture, just entirely within the system.”

As they had decided from the outset, Thiel would not be a claimant in any of these cases and, equally early, Thiel claimed to be interested only in litigating and funding claims that could be expected to survive appeal, were they fortunate enough to reach a positive verdict. “We had the idea early on that there must have been any range of legal violations,” Peter tells me, echoing the thrust of Mr. A’s pitch to him in Berlin the previous April, “but I wanted to find a cause of action that wasn’t libel.” 

The First Amendment was unappealing not because Thiel is a libertarian, though he is, but because as a strategist he understood that it was Gawker’s strongest and most entrenched position: we’re allowed to say anything we want. It challenges the legal system and conventional wisdom where they are the most clearly established. Forget the blocking and tackling of proof and precedent. At an almost philosophical level, the right to free speech is virtually absolute. But as Denton would himself admit to me later, free speech is sort of a Maginot Line. “It looks formidable,” he said, “it gives false confidence to defenders, but there are plenty of ways around if you’re nimble and ruthless enough.” That’s what Thiel was doing now, that’s what his legal time was paid to find. 

Someone from Gawker would observe with some satisfaction to me, many years away from this period of preliminary strategizing from Thiel, that if Thiel had tried to go after Gawker in court for what it had written about him, litigating damages and distress from being outed, for example, he certainly would have lost. This was said as a sort of condemnation of the direction that Thiel ultimately did attack Gawker from. Which is strange because that was the point. The great strategist B. H. Liddell Hart would say that all great victories come along “the line of least resistance and the line of least expectation.” John Boyd, a fighter pilot before he was a strategist, would say that a good pilot never goes through the front door. He wins by coming through the back.

And first, that door has to be located.

“The gating resource here was not capital,” Thiel said. “The gating resource was the ideas and the people and executing it well. It’s not like lawsuits haven’t been brought in the past. It’s something that’s been done, so we were required to think very creatively about this space, what kind of lawsuit to bring.”

In the first year that this conspiracy is picking up steam, Gawker Media would post something like 100,000 articles across its eight sites. Almost none of these pieces see an editor before they go live. In 2012 alone, Gawker would find itself the recipient of multiple leaks of celebrity photos, it would unmask a famous internet troll, it would go after politicians, break technology news, publish controversial first-person essays, repeat gossip, and antagonize the sports world. Most of its posts were ephemeral, simple aggregation of the news and trends of the day. Not all, though.

Contained within Gawker’s hundreds of thousands of articles, Mr. A and Peter Thiel were sure, were the seeds of destruction. How many? One? A handful? A hundred? Thiel had limited him in terms of what the range of violations he was comfortable funding would be, so now his legal team would need to really look, not for the obvious but for the ones that everyone else had missed.

That would be their door. That’s how they would destroy Gawker. 

As an investor, Thiel’s question is always: What do I know about this company that other investors don’t know? In other words: Do we have an edge? It’s only with some sort of informational asymmetry, goes his thinking, that one can not only beat the market but dominate it, and get the kind of return that takes a $500,000 check and turns it into a billion. Or pulls off what no one else thought possible. 

Peter Thiel was looking for Gawker’s version of Al Capone’s tax evasion, a legal mistake that no one else had bothered to enforce, something dismissed potentially even by the person on the other side of the story. The conspirators wanted valid causes of action that did not involve the simple fact of whether a journalist has a right to say something or not. They wanted examples of Gawker’s potentially violating the law, violating a copyright, violating the rights of others in ways that might not be protected under the generous shield offered by the Constitution to reporters and citizens. Not just the kinds of cases that a judge would allow to proceed, but ones that would resonate with a jury of ordinary people in whatever jurisdiction they might find themselves. 

Gawker was designed to give someone an opportunity like this, even if they did not know Thiel was plotting against them. They had always pushed the boundaries. They had courted controversy. They had blown apart the old model of journalism. They published first and edited (and fact checked later). A Gawker writer once explained why he liked working at Gawker, what drew him there: “Ultimately, I would rather work at a place that’s bold enough to fuck up than one that is too afraid to ever risk it.” But would someone ever spend $550 an hour to crawl through everything they ever did to find that mistake? Would they take them to court over it? Who would to get sucked into a knock-down, drag-out fight with the outlet that will say anything and everything? The overwhelming belief of their enemies, as was true of Walter Winchell decades before, was that to sue Gawker was to touch pitch.

Gawker bet they were unbeatable. 

Thiel was willing to call the bluff. 

And he within just a matter of weeks, he would find the perfect weak spot in their defenses. It’s name was Hulk Hogan. 

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.