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RyanHoliday.net - Meditations on strategy and life
Blog

The Best Career Advice I’ve Ever Gotten

At the height of the financial crisis in 1975, Bill Belichick—the now six-time Super Bowl-winning head coach of the New England Patriots—was 23 years old and unemployed. Desperate for a job in football after an assistant position fell through, according to his biographer David Halberstam, he wrote some 250 letters to college and professional football coaches. Nothing came of it except a unpaid job for the Baltimore Colts. 

The Colts’ head coach desperately needed someone for the one part of the job everyone else disliked: analyzing film. 

Most people would have hated this job, especially back then, but it turned out to be the springboard through which the greatest coach in football was launched into his legendary career.

In this lowly position, Belichick thrived on what was considered grunt work, asked for it, and strove to become the best at precisely what others thought they were too good for. “He was like a sponge, taking it all in, listening to everything,” one coach said. “You gave him an assignment and he disappeared into a room and you didn’t see him again until it was done, and then he wanted to do more,” said another.

Most importantly, he made the other coaches look good. His insights gave them things they could give their players. It gave them an edge they would take credit for exploiting in the game. 

It’s a strategy that all of us ought to follow, whatever stage of our careers we happen to be in. Forget credit. Do the work. 

I’m lucky enough someone told me that early on, and I still try to follow it today. Don’t worry about credit, they said. Starting as an assistant in Hollywood, the best thing I could do was make my boss look good. 

Forget credit so hard, they said, that you’re glad when other people get it instead of you.

It ended up being pretty decent advice, but it was nowhere near the right wording. I certainly wouldn’t have moved upwards as quickly as I have if I’d just sat there and worked on the way people thought about my boss.

Now that I’ve been around a bit, I think a better way to express it would be:

Find canvases for other people to paint on.

It’s what I now call the canvas strategy.

I used it as a research assistant for bestselling authors. I used it as Head of Marketing for American Apparel. And I continue to use it with my company Brass Check, advising companies like Google and Complex, as well as multi-platinum musicians and some of the biggest authors in the world.

I even wrote a chapter about it in Ego Is the Enemy.

One of the things I kept coming across in my research was that Belichick wasn’t unique. So many of the greats—everyone from Michelangelo to Leonardo da Vinci to Benjamin Franklin—used the same strategy to become great. The strategy? The canvas strategy.

In the Roman system of art and science, there existed a concept for which we have only a partial analog. Successful businessmen, politicians and rich playboys would subsidize certain favored writers, artists, and performers.

More than just being paid to produce works of art, these artists performed a number of tasks in exchange for protection, food and gifts. One of the roles was that of an anteambulo, literally meaning one who clears the path.

An anteambulo proceeded in front of his patron anywhere they traveled in Rome, making way, communicating messages, and generally making the patron’s life easier. The artists who did this were rewarded with stipends and commissions that allowed them to pursue their art.

That takes humility. The canvas strategy takes humility.

It’s a common attitude that transcends generations and societies—the angry, underappreciated geniuses forced to do stuff she doesn’t like for people she doesn’t respect as she makes her way in the world. How dare they force me to grovel like this. The injustice, the waste.

But when you enter a new field, we can usually be sure of a few things:

  1. You’re not nearly as good or as important as you think you are.
  2. You have an attitude that needs to be readjusted.
  3. Most of what you think you know, or most of what you learned in books or in school, is out of date or wrong.

There’s one fabulous way to work all of that out of your system:

Attach yourself to people in organizations who are already successful and subsume your identity into theirs and move both forward simultaneously.

It’s certainly more glamorous to pursue your own glory, though hardly as effective. Obeisance is the way forward. That’s the other side of this attitude. It reduces your ego at a critical time in your career, letting you absorb everything you can without the obstructions that block other’s vision and progress.

Imagine if for every person you met you thought of some way to help them, something you could do for them, and you looked at it in a way that entirely benefitted them and not you. The cumulative effect this would have overtime would be profound.

You would learn a great deal by solving diverse problems.

You’d develop a reputation for being indispensable.

You’d have countless new relationships.

You’d have an enormous bank of favors to call upon down the road.

That’s what the canvas strategy is about—helping yourself by helping others, making a concerted effort to trade your short term gratification for a longer term payoff.

Whereas everyone else wants to get credit and be respected, you could forget credit. Let others take their credit on credit while you defer and earn interest on the principle.

The strategy part of it is the hardest. It’s easy to be bitter, to hate even the thought of subservience, to despise those who have more means, more experience, more status than you, to tell yourself that every second not spent doing your work or working on yourself is a waste of your gift to insist, I will not be demeaned like this.

Once we fight this emotional and egotistical impulse, the canvas strategy is easy. The iterations are endless.

  • Maybe it’s coming up with ideas to hand over to your boss.
  • Find people, thinkers, up and comers to introduce them to. Cross wires to create new sparks.
  • Find what nobody else wants to do and do it.
  • Find inefficiency and waste and redundancies. Identify leaks and patches to free up resources for new areas.
  • Produce more than everyone else and give your ideas away.

In other words, discover opportunities to promote their creativity, find outlets and people for collaboration, and eliminate distractions that hinder their progress and focus. It’s a rewarding and infinitely scalable power strategy. Consider each one an investment in relationships and in your own development.

If you pick up this mantle once, you’ll see what most people’s egos prevent them from appreciating. The person who clears the path ultimately controls its direction, just as the canvas shapes the painting.

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July 21, 2020by Ryan Holiday
Blog

If You’re Not Seeking Out Challenges, How Are You Going to Get Better?

If it’s easy, you’re not growing. 

It’s like lifting weights: if you can do it without trying, you’re not going to get any stronger.

The whole point—of life, of working out, of work—is to push yourself, and to grow as a result of pushing against and through that resistance. 

A couple years ago, after a book signing, someone proposed to me that I might write a book about the billionaire Peter Thiel’s conspiracy against Gawker Media and its founder, Nick Denton. 

There were more reasons to say no than yes: It was outside my wheelhouse; it would be a ton of work; it would be the kind of project that would upset a lot of people. And frankly, it was personally quite risky… to be writing about a powerful gossip merchant and a right-wing billionaire who had just shut down a media outlet he didn’t like. 

I was also just about to have my first kid and it seemed like it would be terribly difficult to manage a newborn and a new kind of book… particularly one that required me to read something like 20,000 pages of legal documents just to get started. 

So you can imagine what I said. I said yes. 

Although I knew it would be hard, and I knew that it might not work, I could also see that it might be the most interesting thing I ever did. And if it did work, it would be a book unlike almost any other I’d ever write. But mostly, I said yes because a writer betrays their craft if they do not push themselves.

In fact, I think that’s true of all crafts. If you’re not seeking out challenges and getting better through them, what are you doing? And what are you doing it for?

One of my favorite passages in Meditations is this one:

Practice even what seems impossible. The left hand is useless at almost everything, for lack of practice. But it guides the reins better than the right. From practice.

Not everything that’s hard is good of course, but almost everything good is hard. Think about all the things you’re good at. There was a time when you weren’t good at them, right? When they were hard. But you worked at it. Despite feeling deficient and frustrated, and fighting the urge to quit, you saw a glimpse of goodness, you clawed out a bit of progress, you felt a glimmer of confidence, and you chose to keep at it. To keep pushing. And you grew from the fight against the resistance. 

Even more, you found something on the other side of it all—a you that you realized you didn’t entirely know and had possibly never met. You learned something incredibly valuable about yourself: you’re capable of more than you know. 

That’s why we have to fight those urges to quit. That’s why we have to keep at it. That’s why we have to seek out challenges. Because would we know anything about ourselves if we never did?

In my writing career, I have grown from each of the challenges I took up. I was asked to write a piece about Stoicism for Tim Ferriss’ website in 2009—one of the first times my work would be in front of a large audience. Tim is a tough editor and I grew for having that experience. The things I wrote and researched for Robert Greene were so beyond my depths that I was constantly worried I’d be exposed as a fool, but with time, I grew—because of the material and ideas I was exposed to. My first book was like flying off a cliff without a parachute and trying to build a plane on the way down… I made it but just barely. 

In 2016, having reaped the benefits of those decisions, I was sitting in a nice, comfortable spot. I had two books under contract, nearly finished. I had a backlist that was selling. I had a niche applying ancient philosophy basically all to myself. 

So when I got those two surprise emails, first from the billionaire Peter Thiel and later from the founder of Gawker Media, Nick Denton, the decision to write a book about them was essentially gambling all those gains. If it didn’t work, wouldn’t it set me way back in the business? Wasn’t it very likely that I would fail with this project? Isn’t narrative non-fiction a totally different genre than what I know how to do? Isn’t it insane to compete with those other pros?

Perhaps, I thought, but there is also almost no chance that I won’t emerge as a better writer. That was why I jumped at the chance. Forget the business logic. I figured it would make me better at my calling and that was reason enough to do it. 

I got down to work.

It was even harder than I thought. It kicked my ass. It made me feel stupid. I doubted myself everyday. 

But when I emerged, to paraphrase Marcus Aurelius, my left hand was now stronger. It could guide the reins… my practice had seen to that. 

When the book came out, it received rave reviews. The New York Times called it “a profound masterwork,” said I was a “genius” and had written “a helluva pageturner.” (I’ll take it!) Its movie rights were optioned (I can’t say who will play Peter Thiel, but it should be very cool). That was all good.

From a sales perspective, it was slower-going. The book has done very well but has struggled to find its own audience for exactly the reason some people warned me not to take the project on. It was different. It was weird. It wasn’t what people expected from me. It didn’t fit in a nice neat box.  

Yet neither this success nor this struggle is why I look at that book as a massive win for me. 

Defining it early on as an opportunity for growth meant that I controlled the outcome. Even if it had sold another 100,000 copies it would not have made it more successful to me—because the success is there for me on the page. It’s in my mind. It’s in my toolkit, which I am using right now on this article. 

I got better because it was hard. Because I took a risk. Because there was so much resistance. 

This is the essence of “the obstacle is the way” philosophy of Stoicism. Each obstacle, everything that goes wrong is just an opportunity to practice a virtue—to give you a chance to work with your non-dominant hand. One obstacle gives you a chance to practice controlling your temper, another perseverance, another a chance to take a long walk through the park. There is always something you can do.

Including right now, today. 

You are going to face plenty of little crossroads—decisions about how to do things and what things to do. Should you walk the 15 minutes to your meeting or take an Uber? Should you pick up the phone and have that difficult conversation or leave it to an email? Should you apologize and take responsibility or hope it goes unnoticed? Should you swim in the outdoor pool or enjoy the warmth of the indoor one? 

As you weigh these competing options, lean towards the hard one. Let it steer you away from the drift of least resistance. Seneca talked about how a person who skates through life without being tested and challenged is actually depriving themselves of opportunities to grow and improve. 

Jump into the colder pool. Have the tougher conversation. Walk instead of drive. Take ownership where you can. Choose the more difficult option. Seek out the challenge. Lean into it. 

Iron sharpens iron, resistance builds muscle. 

You’ll be better for it—not only for the improvement that comes from the challenge itself, but for the willpower you are developing by choosing that option on purpose. When you have two choices, choose the one that challenges you the most. 

Choose the one, as Marcus would agree, that allows you to take the reins in any situation.

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July 14, 2020by Ryan Holiday
Blog

Every Situation Has Two Handles. Which One Will You Grab?

The last few months have been rough for me, as they have been for most people. Most of my talks have been cancelled. Without retail stores open, physical book sales have fallen by a third. We had two new employees start work on February 15th, in new offices we just had renovated, which now sit empty. 

There have been trying supply chain and inventory issues with Daily Stoic. My retirement accounts were savaged and then bounced back and then savaged like everyone else’s. We estimate our total business losses, so far, to be well into the mid-six figures, and that hurts a lot less than watching my son cry that he can’t see his friends at school. My other son had ear infections we couldn’t go to the doctor for, and the stray cat we rescued managed to get pregnant and have kittens before we could get her fixed. 

So like I said, it’s been rough. That’s one way to see it, anyway. I could also choose to see it as not so bad, considering the fact that, unlike 130,000 other Americans and at least 400,000 others worldwide, none of my family members nor I have died in a pandemic.

Still, it has been rough. It would be untrue to deny it, even if other people have it much, much rougher. But just because something is objectively difficult or complicated or unenjoyable, doesn’t mean that’s what you should focus on. 

“Every event has two handles,” Epictetus said, “one by which it can be carried, and one by which it can’t. If your brother does you wrong, don’t grab it by his wronging, because this is the handle incapable of lifting it. Instead, use the other—that he is your brother, that you were raised together, and then you will have hold of the handle that carries.”

This is a critical life question and particularly relevant right now in light of the mountain of adversity we are facing, individually and collectively. Which handle will we grab?

When I look at the last three months, I don’t grab onto the things that were taken from me. I could grab on to blame or despair. I could grip the anger and frustration and impotence. I could even latch onto some pretty valid excuses to sit around and wait for all the chaos to pass, or…

I could look at what I’ve been able to accomplish despite a quarantine and the obstacles it has presented: 

  • I’ve run and biked and walked more than 1,200 miles
  • I’ve written close to 100,000 words
  • I’ve launched four new challenges and courses for Daily Stoic
  • I’ve recorded over 40 hours of content for the Daily Stoic podcast and YouTube channel
  • I’ve gotten in the pool with my kids almost every day
  • I’ve read a few dozen books and filled over a thousand notecards
  • We’ve had 360 meals together as a family
  • I haven’t missed a bathtime or a bedtime
  • We cleaned out the garage
  • With sales from the Daily Stoic Alive Time Challenge, we raised enough money to provide 75,000 meals
  • We donated $100,000 to Alan Graham’s Community First! Village

Not a bad handle to seize hold of, right?

If you’ve ever been stuck in Los Angeles traffic at night, you know it’s miserable. But if you’ve ever flown into Los Angeles at night and seen the lit-up city from above, you’ve noticed how from a different perspective this same miserable experience can suddenly seem almost beautiful and serene. We call one a traffic jam, the other a light show.

The chaos of international politics can strike fear in us—wars break out, property gets destroyed, people get killed. Yet if you zoom out just slightly—across time, rather than space in this case—all those terrifying CNN updates seem to blur together into an almost coordinated dance of nations lurching towards a balance of power. We call one journalism, the other history.

Same thing, different perspective.

Life is like that. We can look at it one way and be scared or angry or worried. Or we can look at it another way and see an exciting challenge. We can choose to look at something as an obstacle or an opportunity. We can see chaos if we look close, we can see order if we look from afar. 

We can focus on our lack of agency in what has happened or we can focus on what we do control, which is how we respond.

Isaac Newton did some of his best research when Cambridge closed due to the plague. Shakespeare wrote King Lear while he hid out from the plague as well. Ian Fleming, the creator of James Bond, wrote Chitty Chitty Bang Bang while he was laid up in the hospital, expressly forbidden from working on something as tough as a novel. Malcolm X educated himself in prison and turned himself into the activist the world needed. Seneca produced some of his best writing in exile. Marcus Aurelius wrote Meditations while Rome was being scourged by the twin evils of plague and war. 

This is what the idea of Alive Time vs. Dead Time, which I’ve written about before, is really all about: which handle will you grab? The one that bears weight? Or the one that won’t take you anywhere?

So yes, things are rough right now. That’s not your fault. But what you do during these rough times? That’s on you. How are you going to look at things? Will you choose to be miserable or awed? Will you choose to sit around and wait for things to get back to normal or make the most of every second of every day? Will you choose to focus on all the ways this has been a rough few weeks? Or will you choose to step back and look at all the things you still have and still can do?

It’s up to you. It’s always up to you. Because there are always two handles. 

I’ve come to see this pandemic as a radical lifestyle experiment that would have been impossible under any other circumstances. What does zero travel look like? Or full remote work for the team? What if your outside income sources evaporate? What if you completely eliminated meetings? What if you politely excised subtractive people from your life? What if you stopped eating out? What if your day didn’t have to be built around anything you didn’t want to do? What if there was a lot less peer pressure? 

This has been an opportunity to try different things… things that, as it turns out, I much prefer to how things were before. Things I’ll be trying to preserve when “we go back to normal” (which of course, we won’t). 

Given the immense devastation and tragedy of this pandemic, that hardly makes up for what has happened. It would be blasé and offensive to claim that it does. Dialing in a bit better at home, becoming more productive, finding things you like better than what you’re supposed to like—these hardly compensate for the rising death tolls. 

But the Stoics would urge us still not to dismiss this progress we have made as meaningless. Because it isn’t. It’s the only handle we can grab right now. It’s the only meaning and good that can come out of this suffering and uncertainty. 

Which is why I will continue to grab what Thomas Jefferson—paraphrasing Epictetus—would call the “smooth handle.” Because what else am I going to do? What would be better?

I urge you to do the same.

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July 7, 2020by Ryan Holiday
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