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
On August 29, 2018, I met Ryan for the first time. At the time, I was 2 years into a nomadic ski-bum phase & trying to figure out what to do next. Standing outside the Four Seasons in Vail, CO, where he had just given a talk, I asked Ryan if he had any advice. He said, at an inflection point in his own life, he turned down some high-paying job offers to work as a research assistant for Robert Greene. “Because Robert’s life,” he said, “resembled what I wanted for myself.” He tried to call Robert, and, as he knew it would, it went straight to voicemail. Because Robert’s day, Ryan said, is spent reading, researching, thinking, making notecards, and engaging with ideas. That, he said, is what he wanted his typical day to look like too. “So look at the people five to ten years ahead of you in whatever career you’re considering,” Ryan told me. “Does their life look like one you’d want for yourself? Are they who you want to be? Because that’s the trajectory you would be 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 a 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 you’re 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.