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Novak Djokovic almost quit playing tennis in 2010.

A lot of kids dream of being a professional athlete. Djokovic’s earliest memory is being a “seven-year-old boy in Serbia constructing a Wimbledon tennis trophy in my room from improvised materials.” ¹ Unlike most of us with the dream, Djokovic had the talent. One professional tennis player saw him play when he was six years old and said, “This is the greatest talent I have seen since Monica Seles,” then the number 1 player in the world. ²

He turned pro in 2003. By 2008, he was the number three ranked player in the world, a grand slam winner, and in the conversation to win Wimbledon. But after a quarterfinals loss in the 2010 French Open, “I hit a wall,” Djokovic said. He’d been hearing for more than a decade that he had the talent to be number 1. One way to look at that is the way Djokovic looked at it: for more than a decade, he wasn’t enough, wasn’t good enough, wasn’t achieving enough. “I was mentally at one very messed up place.” ³

He first told his parents he was done. Then he went to tell his coach Maria Vajda. When he saw Vajda, he broke down in tears. Vajda encouraged him to let it out and Djokovic did for about as long as it will take me to tell you about someone who was number 1 in their profession.

Rodney Mullen started skateboarding in a little detached garage on his family’s farm in Florida. It wasn’t much, but it was cement—the only cement for miles. It was 1974, a few years before the Ollie was invented. He turned pro in 1980 and over the next ten years, Rodney was the number 1 skateboarder in the sport. He won every freestyle contest he entered but one, and along the way, he invented most of the tricks used today—the flatground ollie, the kickflip, the heelflip and some thirty others. ⁴ In 1989, he started World Industries, the first ever skateboarder-owned company. He sold it in 2003 for $46 million. That year, he was voted the all-time greatest action sports athlete. The following year, he founded Almost Skateboards, which is today one of the most successful companies in skateboarding. Rodney’s in his fifties now and still skateboards every day. He was once asked to what he owes his success, how he got to the top of his profession and has been able to stay there for over four decades:

I’m easily amused…It’s such a gift to be able to look at something and to love it for the sake of it…I have that. I’ve nurtured it in my life. Talent is around. I see people with talent but the one thing they don’t have is that just love of doing it for the sake of it. ⁵

And by now, Djokovic was calming down. “Let’s look back,” Vajda said, “Why did you start playing this sport? Put aside rankings and what you want to achieve, do you really like holding a racket in your hand?” 

Djokovic didn’t say anything for one-mississippi, two-mississippi, “I do. I love holding a racket in my hand. Whether it’s a grand slam final on center court or just a normal public court, I like playing for the sake of playing.” Vajda nodded, “Well that’s your source. That’s what you need to tap into.” 

Still, picking up some burnout symptoms, Vajda told Djokovic to take a few weeks off. Djokovic agreed he would. But he woke up the next day with vitality. He went to the courts, not to train, but to play. “And I never looked back ever since that moment.”

The following season, Djokovic enjoyed one of the greatest seasons in sports history. It was so good that “The 2011 Novak Djokovic tennis season” has its own Wikipedia page. He won 43 straight matches. He won three Grand Slams: the Australian Open, the US Open, and his first Wimbledon. And he finished the year as the number one player in the world. 

“I started to play freely,” he says of that season. “I became the kid that I was when I started playing.” ⁶

It’s strange but true: when you aren’t thinking so much about reaching the pinnacle, you reach it.  

47 years after publishing Man’s Search For Meaning, Viktor Frankl wrote about this paradox. In 1945, he wrote the book in nine days with a conviction that it would be published anonymously. Unlike the dozens of other books he published, the first printing of Man’s Search For Meaning didn’t have his name on the cover. “And so it is both strange and remarkable to me,” Frankl wrote, that it became the book he’s known for. For the rest of his life, Frankl would share what that taught him: “Don’t aim at success—the more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s dedication…In the long run—in the long run, I say!—success will follow you precisely because you had forgotten to think about it.” ⁷

Or suppose it doesn’t. Suppose “success” never follows you. Suppose Rodney Mullen skated for forty years just for the sake of skating and suppose he never won a trophy. Suppose Novak Djokovic played tennis for twenty years just for the sake of playing tennis and suppose he never won Wimbledon. Could we call them “unsuccessful”? I couldn’t.

“So the trick,” Rodney Mullen says, “is to always peel back and ask, why am I doing this in the first place?  I’m still that kid skating in the garage on the farm, you know? And I cling to that.”

Sources:

[1] Novak Djokovic Champion’s Post-Match Interview | Wimbledon 2021

[2] Serve to Win by Novak Djokavic 

[3] Novak Djokovic | Tennisnet

[4] The Mutt: How to Skateboard and Not Kill Yourself by Rodney Mullen

[5] Rodney Mullen | How to Use Pain to Become The Best in the World

[6] Novak Djokovic on Becoming #1 in the World and Overcoming the Odds

[7] Man’s Search For Meaning by Viktor Frankl

Thank you to Greg Shildkrout and Katie McKenzie for reading drafts of this.

In the middle of shooting the fifth episode of The Newsroom, the show’s lead Jeff Daniels fell to a knee. 

“Give me the line again,” he yelled to the script supervisor. “Give me the line again.” She yelled back the line. He just has to repeat it. He can’t. “Give me it again.” She does once then twice more. He can’t keep a single word in his head. “Ok Jeff,” the director said. “Why don’t you go home?” 

In his two decades of acting, Daniels never struggled like this. This was his first time working for screenwriter Aaron Sorkin. Every actor who gets asked about working for Sorkin inevitably mentions the word “dialogue.” Sorkin is known as a master of writing dialogue. 

And as is the nature of working for a master, expectations are high. “You have to memorize mountains of dialogue,” Daniels said. “And then you have to spit it out at a hundred miles an hour.” That means actors can’t do what actors typically do: memorize their lines in the makeup chair. “I’ve seen day-players come in on Newsroom, and they’re trying to learn three pages of Sorkin in the makeup chair, and the flop sweat hits them. I’ve never seen it anywhere else.” ¹

Daniels would come to call it “getting Sorkinized.” He was the first to fall to a knee in that first season of filming The Newsroom but not the last. “We all, at some point, took a knee.” ²

Daniels tells this story when asked how he decides what jobs to take. He said he has to be at least pretty sure the job will be at least pretty hard. Because if it’s not hard, it’s easy. If it’s easy, he’s not getting better. If he’s not getting better, what is he doing?

We’re not done with Daniels. But before I tell you about what happened after he got Sorkinized, I want to tell you something about trees. Trees live off sunlight. Nutrients produced through photosynthesis fuels a tree’s growth. But easy access to light does a tree no good. Ideally, trees spend their first decades in their mothers’ shade. Because in the struggle for light, forester Peter Wohlleben writes, “they develop wood that is incredibly dense.” Youngsters free from this struggle for light grow fast. That means they develop wood that is airy, with plenty of room for fungi and yeasts and smuts and molds and mildews. A tree that doesn’t have to struggle, in other words, rots. “Developing mighty trunks,” Wohlleben writes, “takes a great deal of energy.” It requires that a tree “struggle for every ray of sunlight.” ³

If you don’t have to struggle a little, you’re not growing. If you always pick up the same pound weights, your muscles don’t get stronger. If you always run at the same pace, you don’t get faster. If you always play the same three chords, you don’t get better at playing the guitar. 

I got to be a fly on the wall for a conversation between Ryan Holiday and Chris Bosh. They talked about something I think about often. Chris said it was something he learned from Kobe Bryant: you gotta love the parts that aren’t fun, you gotta love a little struggle. Playing in the NBA is fun. Practicing and conditioning and sacrificing enough to make it to and in the NBA is a struggle. Publishing books is fun. Writing and researching and thinking and rethinking is a struggle. Filming a scene (when you’ve got all the lines in your head) is fun. Memorizing mountains of lines is a struggle. Acing a client presentation is fun. Preparing and ideating and considering that you might not ace it is a struggle. 

Chris said he has this thing he says to himself anytime he’s struggling, “I always like to think, ‘how many people would quit right now?’ That’s the first thing I think about. Then I keep going.” ⁴ 

Jeff Daniels kept going. A few months after getting Sorkinized, he won an Emmy Award for Lead Actor in a Drama Series for the first season of The Newsroom. A few years later, he got a call from Sorkin, who had just acquired the stage rights for To Kill a Mockingbird and wanted Daniels to play Atticus Finch. Sorkin warned him that what they were attempting—adapting a book almost universally beloved for the stage—was probably a “suicide mission.” “I didn’t blink,” Daniels said. “I’ve just been going, ‘if you aren’t challenged, then don’t do this anymore.'” ⁵ The play opened on Broadway in December of 2018. It shattered opening week box office records and became the highest grossing play in Broadway history. 

Struggling is not always a good thing, of course, but good things are almost always on the other side of a little struggle. It’s good to be in the shade struggling for some light. It’s good to pick up a weight that feels a little too heavy. It’s good to run a little faster than your pace. It’s good to reach a point where you want to quit—it’s a wall trying to keep everyone else out too. Keep going. 

Sources:

[1] Jeff Daniels | Smartless

[2] Newsroom’s Jeff Daniels on the Rigors and Rewards of Sitting in the Anchor Chair 

[3] The Secret Wisdom of Nature by Peter Wohlleben

[4] Chris Bosh on Stoicism, Embracing the Process, and Staying Present | Daily Stoic

[5] Broadway’s To Kill A Mockingbird | Jeff Daniels, Aaron Sorkin + More | Talks at Google

Thank you to Greg Shildkrout and Katie McKenzie for reading drafts of this.

In 2008, “In The Heights” won a Grammy and four Tony Awards. At Radio City Music Hall, the entire cast and crew went up to receive the final Tony award presented: Best Musical. Two of them picked up the writer and star of the musical, Lin-Manuel Miranda, and put him on their shoulders. There was fist-pumping, waving, screaming, and smiles.

Forty-four seconds later, the lights shifted and everyone in the audience got up and started exiting. But “In The Heights” director Tommy Kail stopped on stage and stood there by himself. 

Kail first saw the script for “In The Heights” in 2000. He met with Lin-Manuel Miranda in 2002. They got to work and “In The Heights” premiered off Broadway in 2005, then opened on Broadway in 2008. 

Kail was 31 years old that night of the Tony’s and eight of those years were spent working on “In The Heights.” As everyone emptied out of Radio City Music Hall, they talked about what after-party they were attending and what they were going to eat and what they were working on next. Kail stood on stage alone and thought, “Well if this is a pinnacle, and it’s over in an instant, and people are already talking about what’s next, it can’t be about this. It has to be about something more than this.” ¹

We’ll come back to Kail. First, an example of a different director with a different result. 

When Edgar Doctorow first adapted his 1971 novel, The Book of Daniel, into a screenplay, the director Sidney Lumet read it. “[I] thought it was one of the best screenplays I’d ever seen,” Lumet wrote.  

Over a decade later, Lumet finally got a studio on board to make the movie. After casting and rehearsals, the first day of shooting arrived. Six cameras and five-thousand extras were on set. Before he got the cameras rolling, Lumet looked over at Doctorow. “He was weeping,” Lumet writes, “It had been a long wait.” Lumet goes on to describe the experience of working on Daniel with Doctorow—the late nights and early mornings, the arguing and the discussing and the asking and the doubting, the hours of shooting, the hours in the cutting room, the hours on the road doing publicity.  

Daniel released on August 26, 1983. The reviews came in first—it was a critical failure. The numbers came in next—it was a box-office flop. “Despite its critical and financial failure,” Lumet wrote, “I think it’s one of the best pictures I’ve ever done.” On the experience of getting to know and work with Doctorow, “it was a first-rate collaboration.” ²

What Kail realized standing on stage that night at the Tony’s is what Doctorow knew: the outcome is a tiny percentage of the experience.  

The “In The Heights” cast and crew stood on the Radio City Music Hall stage for forty-four seconds. That’s 0.000017% of the eight years Kail spent working on it. ³ To let 0.000017% of an experience determine one’s happiness or satisfaction with the work, Kail realized, is insane.

Yet this is what we do. The poker champion turned author Annie Duke calls it “resulting.” ⁴ Resulting is using the quality of an outcome to determine the quality of what precedes the outcome. It’s letting the Tony awards or the box office results have sway over your happiness or your satisfaction with the work you did. It’s letting the 0.000017% dictate if the other 99.999983% was good or worthwhile or fun or etc. 

On the last run of closing day at Vail one winter, my friend broke his collarbone. It was our 152nd day of skiing that season. His would end with a ride on a ski patrol sled and then to the hospital for surgery. As I wheelchaired him to the car, I made a comment about how it doesn’t get much worse than breaking a bone on the last run of closing day. “Yea it does,” he said, “not having the season we just had.” 

Despite the injury, it was a first-rate season.

Outcomes are an instant, only 0.000017% of the whole pie. Try not to get caught resulting. Treat yourself to the 99.999983%.

Sources: 

[1] Tommy Kail | Little Known Facts 

[2] Making Movies by Sidney Lumet

[3] Thank you Connor Crump for help calculating percentages 

[4] Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts by Annie Duke

Thank you to Joe Donohue and Katie McKenzie for reading drafts of this.

On January 19, 2006, NASA launched the space probe New Horizons. The primary mission was to do a flyby of Pluto. On July 14, 2015, it did. “New Horizons’ almost 10-year, three-billion-mile journey,” NASA explained the day the probe made its approach to Pluto, “took about one minute less than predicted when the craft was launched in January 2006.” ¹

NASA predicted New Horizons’ decade-long journey with 99.99998% accuracy. ² Before launch, NASA was 99.99998% sure about what the next ten years held for New Horizons. 

Can you imagine? If life were more like astrophysics? If you could know how a decision would shake out with 99.99998% accuracy? If before you started a business or wrote a book or quit a job, you were 99.99998% sure it’d all work out?

When I told Ryan Holiday I wanted to start writing on this site, I told him I was just waiting until I knew for certain what I wanted to write about. I told him I started a Google Doc where I’d been writing potential posts to see if any patterns or themes emerged. “Just start,” he said. “You’re trying to map out the whole game. You can only dial up the first couple plays.” 

He then reminded me of the line from Robert Greene, “The need for certainty is the greatest disease the mind faces.” ³

We like certainty. We’d like to see the whole game mapped out before we decide if we’d like to play or not. We’d like the thing we are thinking about doing to be like a trip to Pluto. We want to be 99.99998% sure that the article is good before we publish it. That the party’s going to be fun before we go. That the joke will land before we take it on stage.

Jerry Seinfeld has told a lot of jokes on a lot of stages. If you were to ask me to name a comedian who is certain about their material before going on stage, I would have said Jerry Seinfeld. But then I heard this…

Every time he goes on stage, he said, he tries some new material. If it works, he tells it the next night. If it doesn’t work, he tweaks it or drops it. If you’ve seen him on TV or Netflix—“What you see is what worked. But you’re only seeing 1.5% of what I’ve tried.” ⁴

Jerry Seinfeld can forecast with 1.5% accuracy. He published a book titled with the question every comedian says to every other comedian about a new bit, Is this anything? He says there’s a follow-up question when you see that comedian later, Did it get anything? “All comedians are slightly amazed when anything works.” ⁵

So I’m trying to remind myself that most things are more like comedy than astrophysics. That you can’t be certain. That it’s not a trip to Pluto. That you can’t be 99.99998% sure. And that needing to be is the greatest disease the mind faces—it will prevent you from doing anything.

_

Sources:

[1] NASA’s Three-Billion-Mile Journey to Pluto Reaches Historic Encounter

[2] I first learned about New Horizons’ Pluto flyby in The Psychology of Money by Morgan Housel

[3] Mastery by Robert Greene

[4] Jerry Seinfeld | Sunday Sitdown with Willie Geist

[5] Is This Anything? by Jerry Seinfeld

Thank you to Greg Shildkrout and Katie McKenzie for reading drafts of this. Your feedback made it 99.99998% better.

In June 2018, I cold emailed my favorite writer. I thanked him for his work then offered to work for him for free. 6 months later, I was hired full time as a research and writing assistant. Since then, I’ve helped or observed Ryan Holiday research, write, publish, and market 5 bestselling books, grow his email lists by some 500,000 subscribers, and publish an article a week read by who knows how many people. 

I wrote this piece when Ryan was working on his 12th book, The Boy Who Would Be King. It’s about how the influential figures in a boy’s life helped shaped who he became. But I was hesitant to publish it. I was afraid to put my writing out there and afraid to not get it right and afraid to not perfectly capture all I’ve learned from one of the most influential figures in my life.

Then I got my copy of Ryan’s 13th book, Courage Is Calling: Fortune Favors the Brave, a book I saw come together chapter by chapter in individual Google docs. I reread part 1. Part 1 is about conquering fear. Part 1 cannot be read without feeling like you want to go be a little bit brave, like you want to go do the thing you’ve been afraid to do. So here it goes. Here’s what I’ve learned so far from one of the most influential figures in my life.

(Note: This intro once included the story of how I met Ryan, but one of the first things I learned from him was to get straight to the point. If you’d want to read about how I stumbled into working for my favorite writer, you can read that story here.)

Be Aware of The Trajectory You’re On

When I was first introduced to Ryan’s work, I’d been traveling the world and working odd jobs. I loved it. Then I heard Ryan talk about working for Robert Greene. Robert’s life, he said, resembled one Ryan wanted for himself. When I looked around, at the people five and ten years ahead of me, I saw I was on a path I didn’t want to be on. We often think, ‘once I get this promotion…’ or, ‘once I get that job title…’ What we should do is look at people past that promotion and with that job title. Does their life look like one you want for yourself? Are they who you want to be? Because that’s the trajectory you’re on. 

You Are The Sum Of Your Influences

My friend Colin and I used to watch YouTube videos of our favorite lacrosse players and then go outside and try to mimic them. Later, when he was breaking school records in high school and college, people talked and wrote about his unique style of play. But I saw him for what he was: a beautiful mashup of his favorite players. I once asked Ryan about his unique writing style. He said he found artists he liked and borrowed from them. “The key is that no one has the same combination of influences as you,” he said. “It feels like me because I’m the only person to combine my interests in my way.” 

Production is a Function of Process

A lot of people ask Ryan how he produces so much. My dad has a custom apparel business, and I worked in the factory growing up. While he produces some 60,000 items of decorated apparel each year, no one asks him how he does it. How he does it is he has a warehouse of garments and fabrics and spools of thread and rolls of cad-cut film and thermo film that get pulled and pieced together by skilled embroidery and press operators and then cleaned and trimmed and ironed and inspected and folded and boxed then shipped. Ryan’s production is a function of a similar process. He has a warehouse of notecards with ideas and stories and quotes and facts and bits of research, which get pulled and pieced together then proofread and revised and trimmed and inspected and packaged and then shipped. If you develop a process and commit to that process, Ryan says, books come out the other side. They aren’t feats of genius or works of magic or flashes of inspiration. They’re products of process.

Capture Everything Interesting You Come Across

Each one of Ryan’s books is comprised of thousands of notecards. What he does is he captures everything interesting he comes across. If there’s a good story in a book or a good line in a movie or a good lyric in a song, he writes it down on 4×6 index card and puts it in a box. When he goes through that box, he finds themes and makes connections that later become the idea for a book or a chapter or an article or a daily email or a talk or a product or a. That box of notecards is like an external brain, a tangible memory bank, a private search engine, an idea warehouse, a factory for creative output. It’s very powerful. Whether your job is to make things with your brain or your someone who can’t start a commute or a workout or a load of laundry without first putting on a podcast, capture everything interesting you come across. Cultivate your external brain. 

Consistent Contributions Compound   

I once drove a van along Australia’s East coast. From Wilsons Promontory to Cairns. 2876 miles. Though technically every day we were driving to Cairns, we didn’t wake up in Byron Bay and go, “today, we are driving to Cairns.” We woke up in Byron Bay and said, “today, we are driving two hours to Brisbane.” We woke up each day and covered a little more ground. On a note card, Ryan makes a to-do list every day. Though technically every day he has to work on a book, the to-do list never says, “work on book.” It says things like, “write chapter 3” or “finish intro to part 2”. He wakes up and covers a little more ground on the project. He doesn’t wait for inspiration. He shows up, makes a small but positive contribution to the project, and knows that if he does it enough days in a row, a publishable book is inevitable. Tim Ferris once asked Ryan to what he attributes his ability to get shit done. This, he said, it’s the cumulative process of making a little progress every day. “Compound interest is one of the most powerful forces on earth. And you can apply that to your own work. Every day, if you wake up and you work on something, you get a little bit closer and it grows.” 

You Control How You Respond

There were two chefs who alternated shifts at this cafe I worked at in New Zealand. When a customer made a modification to the dish they ordered, the one chef always cursed the customer—if we thought the pork benny would taste better with salmon, we woulda called it the f*ckin salmon benny. The other chef would always go, “I can do that,” and then make the best salmon benny you ever had. Ryan’s definition of Stoicism is: you don’t control the world around you, you only control how you respond. He’s written about the presumptuousness of the timeless question, What is the meaning of life? As though the world is going to tell you. No, “the world is asking you that question,” he writes. “In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well.” That’s how you give life meaning, “and how to turn every obstacle into an opportunity.” 

You Can’t Avoid Getting Some Of That Mud On You

During my freshman year of high school, I was sitting in English class playing tic-tac-toe against myself. We were tied two-two in a best of five series when I looked to my right. My soon-to-be friend Connor was doing long-division problems in the back of his notebook. In one of my favorite Epictetus passages, he talks about pretending that everyone you spend time with is covered in mud. Every time you rub shoulders with someone, you can’t avoid getting some of that mud on yourself. The people you spend time with, he’s saying, either pull you down with them or pull you up to them. The latter was and is true of being friends with Connor. I’ve also realized it’s true of mentorship. Mentors don’t tell you how to do things. They show how they do things. They show you the standards and expectations they hold themselves to. They show you that they eat lunch with a book in their lap. They show you that they step away each day for some strenuous exercise. They show you, when you check your email at 9 am, that they’ve already written one article and put edits in on another. And over time, you might not even realize you got some of that mud on you.  

Stay A Student 

In November 2016, I moved to Colorado for a job ski instructing. My roommate in employee housing had never skied before. He surprised me when he said he too was hired as a ski instructor. His plan was to use the week before on-mountain training to get just adequate enough to then use those two weeks of training as somewhat of a private lesson. It worked. And he was actually one of the better instructors. The reasons were One: unlike better skiers, he could remember what it was like to not know what he knows. Two: unlike more experienced instructors, he brought to his teaching the excitement of someone who had a recent revelation they want to share. One of the great pieces of writing feedback Ryan once gave me was, “Write for a reader who doesn’t know what you know nor care like you care.” The point was that what I wrote assumed a bunch of knowledge and interest on behalf of the reader. “The job,” he said, “is putting these ideas in packaging that makes them useful, interesting, and relevant to people.” The curse of knowledge makes it hard to be good at this and the curse of experience makes it hard to be good at this for long. The antidote is to, as Ryan’s written, “always stay a student.” To try to remember what it was like to not know what you know. And, to bring the excitement of someone who just had a revelation they want to share.

Which brings me to the final lesson I want to share here…

Build A List

In Perennial Seller, Ryan writes, “If I could give a prospective creative only one piece of advice, it would be this: Build a list. Specifically, an email list.” So I’m starting to build an email list. If you subscribe in the box below, you’ll immediately receive an email from me titled, The Principles of Process: The 5 C’s to Consistent Creative Output. It’s 5 things that have shown up again and again in the processes of creators—authors, shoe designers, songwriters, playwrights, chefs, TV producers, screenwriters, philosophers—I’ve studied and observed.

And then every Sunday around 6 AM (CT), you’ll get an email from me with SIX things I learned, thought were interesting, or found useful from my reading and researching that week. (Read previous issues of the SIX at 6 newsletter here). It’s free and you can unsubscribe if you find it isn’t useful, interesting, and relevant to you.