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RyanHoliday.net - Meditations on strategy and life
Blog

Life Comes at You Fast. So You Better Be Ready.

In 1880, Theodore Roosevelt wrote to his brother, “My happiness is so great that it makes me almost afraid.” In October of that year, life got even better. As he wrote in his diary the night of his wedding to Alice Hathaway Lee, “Our intense happiness is too sacred to be written about.” He would consider it to be one of the best years of his life: he got married, wrote a book, attended law school, and won his first election for public office.

The streak continued. In 1883, he wrote “I can imagine nothing more happy in life than an evening spent in the cozy little sitting room, before a bright fire of soft coal, my books all around me, and playing backgammon with my own dainty mistress.” And that’s how he and Alice spent that cold winter as it crawled into the new year. He wrote in late January that he felt he was fully coming into his own. “I feel now as though I have the reins in my hand.” On February 12th, 1884 his first daughter was born.

Two days later, his wife would be dead of Bright’s disease (now known as kidney failure). His mother had died only hours earlier in the same house, of typhoid fever. Roosevelt marked the day in his diary with a large “X.” Next to it, he wrote, “The light has gone out of my life.”

As they say, life comes at you fast. 

Have the last few weeks not been an example of that?

In December, the Dow was at 28,701.66. Things were good enough that people were complaining about the “war on Christmas” and debating the skin color of Santa Claus. In January, the Dow was at 29,348.10 and people were outraged about the recent Oscar nominations. In February, when the Dow reached a staggering 29,568.57, Delta Airlines stock fell nearly 25% in less than a week, as people argued intensely over a message from Delta’s CEO about passengers reclining their seats. Even in early March, there were news stories about Wendy’s entering the “breakfast wars” and a free stock-trading app outage that caused people to miss a big market rally.

And that was just in the news. Think about what you busied yourself with at home during that same period. Maybe you and your wife were looking at plans to remodel your kitchen. Maybe you were finally going to pull the trigger on that Tesla Model S for yourself—the $150,000 one, with the ludicrous speed package. Maybe you were fuming that Amazon took an extra day to deliver a package. Maybe you were frustrated that your kid’s room was a mess. 

And now? How quaint and stupid does that all seem?

Depending on the day you look, years of market gains have now been taken back. 47 million people are projected to be added to the unemployment rolls in the US. The death count from what was dismissed as a mere respiratory flu and the left’s latest hoax is now inching towards 170,000 and there are millions more confirmed cases worldwide. There have been runs on supplies. Hospitals are maxing out ventilators. The global economy has essentially ground to a halt. 

Life comes at us fast, don’t it?

It can change in an instant. Everything you built, everyone you hold dear, can be taken from you. For absolutely no reason. Just as easily, you can be taken from them. This is why the Stoics say we need to be prepared, constantly, for the twists and turns of Fortune. It’s why Seneca said that nothing happens to the wise man contrary to his expectation, because the wise man has considered every possibility—even the cruel and heartbreaking ones.

And yet even Seneca was blindsided by a health scare in his early twenties that forced him to spend nearly a decade in Egypt to recover. He lost his father less than a year before he lost his first-born son, and twenty days after burying his son he was exiled by the emperor Caligula. He lived through the destruction of one city by a fire and another by an earthquake, before being exiled two more times.  

One needs only to read his letters and essays, written on a rock off the coast of Italy, to get a sense that even a philosopher can get knocked on their ass and feel sorry for themselves from time to time. 

What do we do?

Well, first, knowing that life comes at us fast, we should be always prepared. Seneca wrote that the fighter who has “seen his own blood, who has felt his teeth rattle beneath his opponent’s fist… who has been downed in body but not in spirit…”—only they can go into the ring confident of their chances of winning. They know they can take getting bloodied and bruised. They know what the darkness before the proverbial dawn feels like. They have a true and accurate sense for the rhythms of a fight and what winning requires. That sense only comes from getting knocked around. That sense is only possible because of their training.

In his own life, Seneca bloodied and bruised himself through a practice called premeditatio malorum (“the premeditation of evils”). Rehearsing his plans, say to take a trip, he would go over the things that could go wrong or prevent the trip from happening—a storm could spring up, the captain could fall ill, the ship could be attacked by pirates, he could be banished to the island of Corsica the morning of the trip.

By doing what he called a premeditatio malorum, Seneca was always prepared for disruption and always working that disruption into his plans. He was fitted for defeat or victory. He stepped into the ring confident he could take any blow. Nothing happened contrary to his expectations. 

WATCH: Ryan Holiday speaks about premeditatio malorum

Second, we should always be careful not to tempt fate. 

In 2016 General Michael Flynn stood on the stage at the Republican National Convention and led some 20,000 people (and a good many more at home) in an impromptu chant of “Lock Her Up! Lock Her Up!” about his enemy Hillary Clinton. When Trump won, he was swept into office in a whirlwind of success and power. 

Then, just 24 days into his new job, Flynn was fired for lying to the Vice President about conversations he’d had with Sergey Kislyak, the Russian ambassador to the United States. He would be brought up on charges and convicted of lying to the FBI. 

Life comes at us fast… but that doesn’t mean we should be stupid. We also shouldn’t be arrogant.

Third, we have to hang on. Remember, that in the depths of both of Seneca’s darkest moments, he was unexpectedly saved. From exile, he was suddenly recalled to be the emperor’s tutor. In the words of the historian Richard M. Gummere, “Fortune, whom Seneca as a Stoic often ridicules, came to his rescue.”

But Churchill, as always, put it better: “Sometimes when Fortune scowls most spitefully, she is preparing her most dazzling gifts.”

Life is like this. It gives us bad breaks—heartbreakingly bad breaks—and it also gives us incredible lucky breaks. Sometimes the ball that should have gone in, bounces out. Sometimes the ball that had no business going in surprises both the athlete and the crowd when it eventually, after several bounces, somehow manages to pass through the net. 

When we’re going through a bad break, we should never forget Fortune’s power to redeem us. When we’re walking through the roses, we should never forget how easily the thorns can tear us upon, how quickly we can be humbled. Sometimes life goes your way, sometimes it doesn’t. 

This is what Theodore Roosevelt learned, too. 

Despite what he wrote in his diary that day in 1884, the light did not completely go out of Roosevelt’s life. Sure, it flickered. It looked like the flame might have been cruelly extinguished. But with time and incredible energy and force of will, he came back from those tragedies. He became a great father, a great husband, and a great leader. He came back and the world was better for it. He was better for it.

Life comes at us fast. Today. Tomorrow. When we least expect it. Be ready. Be strong. Don’t let your light be snuffed out.

April 28, 2020by Ryan Holiday
Blog

All You Need Are a Few Small Wins Every Day

We have a false picture about how success happens.  Because we often see only the results and almost never the process of things, we tend to think that the finished product—a book, being in shape, being wise—is impressive, and therefore the process by which that event was created must have been equally brilliant. 

In fact, it’s usually the opposite. 

Success, like the proverbial sausage, is much less pretty when you see how it’s made. 

I make no pretensions about being wise or in shape, but I do know books well. I also remember equally well how I thought authors created them back when I was solely a reader. I assumed it must be some magical, special process.

If only that were so…

The single best rule I’ve heard as a writer is that the way to write a book is by producing “two crappy pages a day.” It’s by carving out a small win each and every day—getting words on the page—that a book is created. Hemingway once said that “the first draft of anything is shit,” and he’s right (I actually have that on my wall as a reminder). 

While it would be wonderful if books could be created through raw genius, if we could spit fire each time we sat down at the keyboard, that’s not how it goes. Instead, the best writers have routines that put their asses in the chair and create opportunities to move the ball slightly forward each day. Enough of these small actions strung together—reviewed, dissected, iterated upon—produces publishable work. 

It might even produce things that sell like crazy or take people’s breath away.

That might be less glamorous, but the upside is that it means it’s much more accessible. 

Businesses are also built by humble means—good ones, anyway. Sure, the WeWorks of the world get all sorts of attention for their ambitious plans for taking over the world, and their stratospheric valuations can make it seem like a viable strategy. But just as often, these companies collapse or implode, and in the end not even the bones or foundation remain… because they never existed in the first place. They were fictions, created in a flash while no one was watching.

Trees that grow tall and live long grow slowly—especially at first—but then grow steadily. They may be underground a long time, and a vulnerable sapling for longer still, but like a good idea or a new habit, once the roots are in, they’re hard to dislodge. So it goes with businesses and net worths. Plutarch tells the story of a rich Delian ship-owner who was asked how he built his fortune. “The greater part came quite easily,” he said, “but the first, smaller part took time and effort.”

How does that work?

Creating anything of consequence or magnitude requires deliberate, incremental and consistent work. At the beginning, these efforts might not look like they are amounting to much. But with time, they accumulate and then compound on each other. Whether it’s a book or a business or an anthill or a stalagmite, from humble beginnings come impressive outcomes.

A friend of mine, Pete Williams, once surprised me with a stat a few years ago: 10% improvements across just, say seven, categories in a business would combine to mean doubling your profits. 

This is the approach that I apply to my writing, to my business, and my personal life: When I am not creating, I look for areas I can make small tweaks. How can the subject lines of my emails be better? Could my art be better? Where do I have leaks (of time, money, energy) in my business? Are there habits or systems that are holding me back? What groundwork can I lay now that might come in handy in the future? What investments can I make? What deals can I make (or renegotiate) to improve the health of my finances or the quality of my products?

In one of his most famous letters to Lucilius, Seneca gives a pretty simple prescription for the good life. “Each day,” he wrote, “acquire something that will fortify you against poverty, against death, indeed against other misfortunes, as well and after you have run over many thoughts, select one to be thoroughly digested that day.” 

One gain per day. That’s it. 

George Washington’s favorite saying was “many mickles make a muckle.” It was an old Scottish proverb that illustrates a truth we all know: things add up. Even little ones. Even at the pace of one per day. 

The Stoics believed it was the little things that added up to wisdom and to virtue. What you read. Who you studied under. What you prioritized. How you treated someone. What your routine was like. The training you underwent. What rules you followed. What habits you cultivated. Day to day, practiced over a lifetime, this is what created greatness. This is what led to a good life.

“Well-being is realized by small steps,” Zeno would say looking back on his life, “but is truly no small thing.” Which is why today and every day, you need to think about those little things. They are worth sweating. You need to create good habits. You need to stick to your rules. You can’t make excuses to yourself, saying “Oh, this doesn’t matter.” 

Because it adds up. Because it determines what you’ll accomplish, and what you won’t. Most important, it determines who you are.

No longer naive about the process, today I focus on improving a little bit every day, personally and professionally. I know that cumulatively this has enormous impact. It’s not as sexy as transformative reinvention or bold, risky bets, but it’s dependable and it works. It’s something I control. 

No one can stop me from showing up. From getting better in the areas that most people don’t pay attention to. From what I do when nobody’s watching.

Epictetus called it fueling the habit bonfire. That’s what I try to do day in and day out. 

Even this article is an example. How it turned out is a far cry from where it started—as an idea on a notecard, to an item on my to-do list which became a commitment I honored, which became a piece I spent time on across several days, which I returned to when I had tweaks and improvements, which was edited by a team, and then finally published.

Is it the best thing ever written? Absolutely not. But I am better for writing it, and it is better for the work I put into it, and the piece I write next will be better still. 

April 21, 2020by Ryan Holiday
Blog

The Important Thing Is to Not Be Afraid

In scary times, it’s easy to be scared. Events can escalate at any moment. There is uncertainty. You could lose your job. Then your house and your car. Something could even happen with your kids.

Of course we’re going to feel something when things are shaky like that. How could we not? 

Even the Stoics, who were supposedly masters of their emotions, admitted that we are going to have natural reactions to the things that are out of our control. You’re going to feel cold if someone dumps a bucket of water on you. Your heart is going to race if something jumps out from behind a corner. These are things the Stoics openly discussed.

They had a word for these immediate, pre-cognitive impressions of things: phantasiai. No amount of training or wisdom, Seneca said, can prevent us from having these reactions. 

What mattered to them, and what is urgently needed today in a world of unlimited breaking news about pandemics or collapsing stock markets or military conflicts, was what you did after that reaction. What mattered is what came next. 

There is a wonderful quote from Faulkner about this very idea. 

“Be scared,” he wrote. “You can’t help that. But don’t be afraid.”

A scare is a temporary rush of a feeling. Being afraid is an ongoing process. Fear is a state of being.

The alertness that comes from being startled might even help you. It wakes you up. It puts your body in motion. It’s what saves prey from the tiger or the tiger from the hunter. But fear and worry and anxiety? Being afraid? That’s not fight or flight. That’s paralysis. That only makes things worse. 

Especially right now. Especially in a world that requires solutions to the many problems we face. They’re certainly not going to solve themselves. And inaction (or the wrong action) may make them worse, it might put you in even more danger. An inability to learn, adapt, to embrace change will too. 

There is a Hebrew prayer which dates back to the early 1800s: כל העולם כולו גשר צר מאוד והעיקר לא לפחד כלל. “The world is a narrow bridge, and the important thing is not to be afraid.”

The wisdom of that expression has sustained the Jewish people through incredible adversity and terrible tragedies. It was even turned into a popular song that was broadcast to troops and citizens alike during the Yom Kippur War. It’s a reminder: Yes, things are dicey, and it’s easy to be scared if you look down instead of forward. Fear will not help.

What does help?

Training. Courage. Discipline. Commitment. Calm. But mainly, that courage thing—which the Stoics held up as the most essential virtue. 

One of my favorite explanations of this idea comes from the Canadian astronaut Chris Hadfield. “It’s not like astronauts are braver than other people,” he says. “We’re just, you know, meticulously prepared…” Think about someone like John Glenn, the first American to orbit the earth, whose heart rate never went above a 100 beats per minute the entire mission. That’s what preparation does for you. 

Astronauts face all sorts of difficult, high stakes situations in space—where the margin for error is tiny. In fact, on Chris’ first spacewalk his left eye went blind. Then his other eye teared up and went blind too. In complete darkness, he had to find his way back if he wanted to survive. He would later say that the key in such situations is to remind oneself that “there are six things that I could do right now, all of which will help make things better. And it’s worth remembering, too, there’s no problem so bad that you can’t make it worse also.” 

That’s the difference between scared and afraid. One prevents you from making things better, it may make them worse. 

After the stock market crash in October 1929, America faced a horrendous economic crisis that lasted ten years. Banks failed. Investors were wiped out. Unemployment was some 20 percent. Herbert Hoover, who’d only been in office barely six months when the market collapsed, tried and failed repeatedly for the next 3.5 years to stem the tide. FDR, who succeeded him, would have never denied that things were dangerous and that this was scary. Of course it was. He was scared. How could he not be? Yet what he counseled the people in his now-legendary first inaugural address in 1933 was that fear was a choice, it was the real enemy to be fought. Because it would only make the situation worse. It would destroy the remaining banks. It would turn people against each other. It would prevent the implementation of cooperative solutions. 

And today, whether the biggest problem you face is the coronavirus pandemic or the similarly dire economic implications—or maybe it’s both those things plus a faltering marriage or a cancer diagnosis or a lawsuit—you have to know what the real plague to avoid is. 

This life we’re living—this world we inhabit—is a scary place. If you peer over the side of a narrow bridge, you can lose the heart to continue. You freeze up. You sit down. You don’t make good decisions. You don’t see or think clearly. 

The important thing is that we are not afraid. That we don’t overthink things. That we don’t get distracted with the worst-case scenario on top of the worst-case scenario on top of the collision of two other worst-case scenarios. Because that doesn’t help us with what’s right in front of us right now. It doesn’t help us put one foot in front of the other, whether it’s on a spacewalk or a tough business call. It doesn’t help us slow our heart rate down whether we’re re-entering the earth’s atmosphere or watching a plummeting stock portfolio. It doesn’t help us remember that we’ve trained for this, that there is a playbook for how to proceed. 

Remember, Marcus Aurelius himself faced a deadly, dangerous pandemic. His people were panicked. His doctors were baffled. His staff and his advisors were conflicted. His economy plunged. The plague spanned fifteen years of his reign with a mortality rate of between 2-3%. Marcus would have been scared—how could he not have been? But he didn’t let that rattle him. He didn’t freeze. He didn’t relinquish his ability to lead. He got to work. 

“Don’t let your imagination be crushed by life as a whole,” he wrote to himself, as it was happening. “Don’t try to picture everything bad that could possibly happen. Stick with the situation at hand, and ask, ‘Why is this so unbearable? Why can’t I endure it?’ You’ll be embarrassed to answer.” 

The crisis could have crippled him. But instead he stood up. He not only endured it, but he was a hero. He saved lives. He prevented panic from turning the battle into a rout. 

Which is what we must do today and always, whatever we’re facing. 

We can’t give into fear. We have to repeat to ourselves over and over again: It’s OK to be scared, just don’t be afraid. We repeat: The world is a narrow bridge and I will not be afraid. 

We have to focus on the six things, as Chris Hadfield might say, that we can do to make it better. And we can’t forget that there are plenty of things we can do to make things worse. Foremost among them, giving into fear and making mistakes.

Rather, we have to keep going. Like the thousands of generations who have come before us. Because time marches in only one direction—forward. 

April 6, 2020by Ryan Holiday
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