How Does He Do It?
Ryan Holiday’s 17th book, Wisdom Takes Work, releases on October 21st. As his research assistant for the past 7 years, it’s around this time with each new book that I’m asked even more often a question I’m often asked, How does he do it? How does he manage and maintain this prolific output? The truth is…I don’t exactly know. But I’m fascinated by it too.
The work it takes to be consistent, productive, persistent, prolific, and wise—that’s the theme of this SIX at 6…
Alright…Can You Farm?
The stand-up comedian Mitch Hedberg worked his ass off for years and years to become a great comedian. When his comedy finally started breaking through and finding an audience, people started asking him to do other things. People would ask to write movie scripts, to be an actor, to host this show and write for that one. “They ask me to do things that’s related to comedy but not comedy,” Hedberg said. “It’s as though if I was a cook, and I worked my ass off to become a good cook, they say, ‘Alright, you’re a cook—can you farm?” I once heard Ryan say: “Compound interest is one of the most powerful forces on earth. And you can apply that to your own work.” The first rule of compounding, they say, is to never interrupt it unnecessarily. There’s a tendency for creators to break this first rule of compounding, interrupting their progress every time there’s a new trend, tool, algorithm, opportunity, or offer to try their hand at another medium. He experiments and modifies from time to time to be sure, but the core of what Ryan does hasn’t really changed since he started working towards becoming a writer: he reads to collect material to write his books. He has never interrupted his progress towards becoming a great cook, if you will, by jumping on offers to try to farm.
You Reap What You’ve Sown
When Ryan first sat down to try to write about Abraham Lincoln in what would open Part 3 of Wisdom Takes Work, the writing wasn’t coming easily. He wouldn’t say he was experiencing writer’s block because he doesn’t believe there’s such a thing. Rather, it was a signal: he needed to do more work. So he immersed himself in notecards he’d previously made from Lincoln biographies he’d previously read. He read many more biographies and made many more notecards. He interviewed people who knew more about Lincoln than he did. And after spending hundreds of hours immersed in all things Lincoln, when he sat down to try again to write about the man, the writing came easy. He wouldn’t say he was experiencing a visit from the muses because he doesn’t believe there’s such a thing. Rather, it was a signal: he had done the work. “Wisdom,” Ryan writes in the new book, “is a lagging indicator of work done long ago, the fruit nurtured from the seed planted long ago. You can only reap what you have sown.” And so it goes with creative output: it’s the fruit nurtured from seeds planted in the past. Ryan writes elsewhere: “This is what keeps me moving—knowing that I have to keep filling and refilling the creative well. Knowing that creative output is a lagging indicator of a lot of hours of tedious work. Knowing that if I want to publish more books in the future, the only question is, am I doing the work now?”
While They’re Deciding, Make Even More Art
In the early-1960s, Andy Warhol made hundreds of plywood box sculptures, meticulously constructed, painted, and silkscreened to exactly replicate the corrugated cardboard shipping cartons that brands used to deliver bulk goods—Heinz ketchup, Brillo soap pads, Kellogg’s corn flakes, and Campbell’s tomato juice—to grocery stores. On April 21, 1964, Warhol exhibited these box sculptures at New York City’s Stable Gallery. Across multiple rooms, he arranged hundreds of boxes to stage various steps of the supply chain: boxes were scattered like new arrivals in a warehouse, organized like inventory in a stockroom, set up like product in an end-cap display, and stacked four-high, as if waiting to be wheeled away on a dolly cart. The exhibit was a spectacular failure. Critics wrote nasty things about Warhol. Fans were baffled by the sculptures. Even longtime friends and supporters backed away, distancing themselves so as to not be thought associated with him. “Warhol refused to linger over the setback,” we’re told, “taking instead the advice he would often give to other artists: ‘Don’t think about making art. Just get it done. Let everyone else decide whether it’s good or bad, whether they love it or hate it. While they’re deciding, make even more art.’” There’s a great video of Ryan receiving a call from his agent with news that his book had debuted at #3 on the New York Times bestseller list. That’s great news, Ryan said, “and I’ll get back to work on the next book.” The best way to not let a project’s spectacular success get you too high or its spectacular failure get you too low, Ryan likes to say, is to be already working on the next project by the time the many deciding factors decide that success or failure.
Get Tied Down
The musical Hamilton opened on Broadway in the summer of 2015 and quickly became a sensation. Famous people were in the audience every night. There were afterparties. There were people telling the show’s creator Lin-Manuel Miranda that he was a genius. Asked, “What about your life allowed you to be able to handle the crazy success of the show?”—Lin said, “Vanessa [Lin’s wife]…and my first kid. He was born two weeks before rehearsal started.” So instead of attending afterparties with famous people calling him a genius, Lin went home to his wife and newborn. “All the noise and things that derail folks—like the getting invited to parties and the famous people—I had to say no to ninety percent of it,” Lin said. “Because I had to sleep eight hours and I knew I was gonna wake up twice and change diapers. My family really saved my ass, because I think that’s how you lose it.” Ryan often similarly credits his wife and kids for having not been derailed by his success and all the temptations that come with it. “People are concerned that having kids or getting married will tie you down” he says. “And it does. It objectively does. But it ties you down to reality. It tethers you to the earth. It keeps you from spinning off the planet.”
Fuck The Marshmallows
In his book Turning Pro, Steven Pressfield tells the story of watching a famous horse trainer working with his thoroughbreds. “I had imagined that the process would be something hard-core like Navy SEAL training,” Pressfield writes. “To my surprise, the sessions were more like play.” The work was serious and demanding, but the trainer’s main concern was getting the horses to love running. “Horses understand the whip,” the trainer explained, “but I don’t want a racer that runs that way. A horse that loves to run will beat a horse that’s compelled, every day of the week. I want my horses to love the track. I want my exercise riders to have to hold them back in the morning because they’re so excited to get out and run.” Pressfield then references the famous marshmallow test where children who were able to sit for three minutes with a marshmallow on the table in front of them without eating it were rewarded with two marshmallows when the experimenter returned. But similar to the way a horse that loves to run will beat a horse that’s compelled, Pressfield adds, one who does their work for its own sake will always beat those doing it for future rewards. “[In the Bhagavad Gita] Krishna said we have the right to our labor, but not to the fruits of our labor,” he writes. “He meant that the piano is its own reward, as is the canvas, the barre, and the movieola. Fuck the marshmallows.”
This seems to be Ryan’s attitude, which I think is ultimately the answer to how he does it, how he manages and maintains his prolific output: he finds the labor rewarding. He loves the track. He’s not in it for the marshmallows.