28 Lessons From Great Writers, Artists And Creators On Mastering Your Craft

Mastery doesn’t just happen. It’s a commitment. Not of 10,000 hours or 20,000 hours, or of any specific number but of a lifetime of work and dedication. It’s an incremental, iterative journey. You don’t magically arrive. Ever. You just strive to get closer.

But there are principles—a process—that must be followed if this is to happen. These principles are lessons we can deduce from the greats, advice they have given to their own students, quotes that have been passed down to us. If we want to be great at what we do—whether that’s writing or painting or public speaking or investing—we would do well to observe and follow them.

1. Always Stay a Student— “It is impossible to learn that which one thinks one already knows,” Epictetus says. The worst thing you can do—at any point of your mastery pursuit—is to assume you have figured it all out. It’s on you if you let pride and ego sneak on you and convince you it’s the case.

2. Seek Out Negative Feedback — You know you are working with a master when they constantly ask how to improve and learn. Anyone who has collaborated with bestselling author and entrepreneur Tim Ferriss know this—if he asks you to take a look at his writing for example, you’d get this question first: “What should I cut?” He wants to know what people didn’t like—so he can improve it or get rid of it.

3. Find Your Torture— On the Howard Stern show, Jerry Seinfeld was explaining how it never gets easier. How it is all work. He joked that “your blessing in life is when you find the torture you’re comfortable with.” For me, that’s writing—I’m grateful that it’s so hard. That Allen Iverson clip: We’re talking about practice. Yeah, love practice. The best ones always do.

4. Be Ok With Sucking — Hemingway said that the first draft of everything is shit. So be OK with producing shit at first. It’s how you get better.

5. Find Your Plus, Minus and Equal — The MMA trainer Frank Shamrock works fighters through a system called +, -, =. Everyone needs to work with someone better than them, equal to them and someone who they can teach. Who are yours?

6. Take Small Steps — As Pat Riley, one of the greatest NBA coaches, put it “Excellence is the gradual result of always striving to do better.” Notice that he says gradual. It’s about the small steps you can take each and every day to make a tiny bit of improvement.

7. Say Little, Do Much — If you are a writer, don’t be the person who tweets “I’m working on my novel.” Be too busy writing for that. Helen Simpson has “Faire et se taire” from Flaubert on a Post-it near her desk, which she translates as “Shut up and get on with it.”

8. Do The Grunt Work — In my own career, I started as an assistant…I worked my way up to being a research assistant. I would have done anything. If I was starting over again, I’d be willing to do more than anything. Because that’s how you learn and how you build relationships. It’s worth noting that Ben Franklin started as an apprentice in a printshop. He did the grunt work (until he was good enough to run far away from it).

9. Do The Deep Work — You need to develop routines and practices to arrive at that place of intense concentration and cognitive focus where real progress is made. Producing a book, that takes deep work. Developing a new insight in science or psychology—that’s the product of deep work. An easy place to start? Remove all time-sucking apps on your phone. See how much better you feel and how much more you’re able to accomplish.

10. Beat Resistance Into Submission — Every artist struggles. Every artist feels something preventing them from getting where they want to go. Then they pick up The War of Art and suddenly have a name for that mysterious force: The Resistance. The biggest enemy of progress in any craft lies within us: The voice that tells us to work tomorrow, that we are not ready, that we are not good enough, that we don’t have what it takes, that we should be off doing this or that thing instead of sitting down on the chair and writing—a voice heard by creatives of any stripe, the ever-present voice of self-sabotage. There’s only one way out: you beat it into submission.

11. Always Ask Questions — Peter Drucker, one of last century’s most prominent business thinker and strategist put it well: “My greatest strength as a consultant is to be ignorant and ask a few questions. I can only ask questions. The answers have to be yours.” In my time as an apprentice I did the same thing. Can you show me an example? Do you mean like this? Here’s what I started with, is this close? Am I doing a good job? What else can I do? The jobs and mentors I was lucky enough to get—most of those opportunities came because I reached out to ask smart people some questions I had (which is a lot better way to get a mentor than asking “Will you be my mentor?”).

12. Follow The Process — The road to mastery is just that, a road. And you travel along a road in steps. Excellence is a matter of steps. Excelling at this one, then that one and then the one after that. This is the process—it is what Nick Saban, the famous coach at Alabama teaches his football players: Don’t focus on winning the championship or even the game you are playing. Focus on the smallest task in front of you—and excel at it. That’s how you get to mastery too, and masterful work. Piece by piece.

13. Access What’s Within You — The reason you follow the process is because you are capable of greater things than you know—producing that work requires wielding talents that no person is strong enough to summon on command (we can only do it by the process, from a flow state). Many artists have trouble looking back on their work, actors have trouble watching their own movies. It feels foreign and strange. That’s because it wasn’t created by them. It was created by the process. It was created by something deep inside them.

14. Don’t Break The Chain —  Jerry Seinfeld once told a young comic that the secret to his success was a big calendar he kept on his wall. Each day, if he wrote, he allowed himself to put a big X across that date on the calendar. After a few weeks, there would be a long string of days in a row of writing. What kept him going was a sense of duty to protect and not break that chain.

15. Don’t Slow Down — In ultra-marathoner Rich Roll’s memoir, Finding Ultra, there is a line I think about often: that it’s not about how fast you go, it’s about who slows down the least—who quits last. Keep going, don’t slow down, that’s how you get better.

16. Read Voraciously — People have been moving West, leaving school, investing their savings, getting dumped or filing for divorce, starting businesses, quitting their jobs, fighting, and dying for thousands of years. They’ve also been doing the job or craft that you’re trying to do for centuries. This is all written down, often in the first person. Read it. You must learn from this knowledge. Do not skip it.

17. Consume Great Art Voraciously — Where does inspiration come from? Many places but one of the best is in the great art from the centuries. Don’t focus on what’s popular now. Root yourself in the great. Rick Rubin, the record producer who has worked with everyone from Jay Z to Adele, urges his artists not to think about what’s currently on the airwaves. “If you listen to the greatest music ever made, that would be a better way,” he says, “to find your own voice to matter today than listening to what’s on the radio and thinking: ‘I want to compete with this.’”

18. Utilize the ‘Draw-Down Period’ — John Boyd was one of the most brilliant strategic minds of the 20th century and the one responsible for the F-15 and F-16 fighter jets. Before he would jump into an idea and go full steam, he had a pre-production phase, a time he called his ‘draw-down period.’ After the ideation phase, you must sit with the discomfort and not immediately rush into creation. Pause and think it through.

19. Be Intentional — One time I asked Robert Greene, author of The 48 Laws of Power and multiple other timeless and important works, how do you make these books that last so long? What’s the secret? His answer was simple: “It starts by wanting to create a classic.” How do you become a master? Same thing: It starts by wanting—needing—to become one.

20. Apprentice Under Someone Great — There is a reason that apprenticeships have been directly related with mastery for centuries. “Go directly to the seat of knowledge,” Marcus Aurelius admonished. Many of history’s greats—from Michelangelo to Leonardo da Vinci to Ben Franklin—they all had a mentor in one form or another.

21. Recommit Every Single Day — Another one from Steven Pressfield: “Turning pro is like kicking a drug habit or stopping drinking. It’s a decision to which we must recommit every day. Twelve-step programs say “One Day at a Time.” The professional says the same thing.” Every day you will face Resistance. Most days will be a challenge. Every day you will have to recommit.

22. Organize Your Knowledge — I’ve already written about my notecard taking process that I learned from Robert Greene when I was his research assistant. All I can say is that since learning it about 10 years ago, it has totally transformed my process and drastically increased my creative output. It’s responsible for helping me publish five books in five years, (along with other books I’ve had the privilege of contributing to), write countless articles published in newspapers and websites, send out my reading recommendations every month, and make all sorts of other work and personal successes possible. Whether you are a barista, movie director or an aspiring entrepreneur, you need to develop a system that catalogs lessons and ideas learned that you can constantly refer back to.

23. Beat Back The Arrogance — These words from Wynton Marsalis, the Pulitzer-prize winning musician and composer, serve as a necessary reminder when you begin to experience success: “You can tell when someone is truly humble, because they consistently observe and listen, the humble improve. They don’t assume, ‘I know the way.’ Humility engenders learning because it beats back the arrogance that puts blinders on. It leaves you open for truths to reveal themselves.”

24. Learn from Everyone—Even the People You Don’t Like — Emerson’s line: “Every man I meet is my master in some point, and in that I learn of him.” A master lives that.

25. Go All In — In The 33 Strategies of War, Robert Greene talks about the “death ground strategy” — that when soldiers have no escape, or are backed into a corner, they fight better and are often impossible to defeat. I moved across the country, left my job to write my first book. It wasn’t a fun side project. I had to step up my game if I wanted to survive. I had to get better if I wanted it to work.

26. Don’t Lie to Yourself — A lot of the advice in this piece is about the sheer quantity of work that you need to produce if you want to reach mastery. There is no way around it—you have to put the hours in. Lots and lots of hours. But don’t lie to yourself how much you need to work. Sleep is important, family is important, reflection is important. Pushing yourself past the point of diminishing returns is not. As Robert Louis Stevenson wrote “Perpetual devotion to what a man calls his business, is only to be sustained by perpetual neglect of many other things.”

27. Forget Passion — Contrary to how most advice goes, you don’t actually need passion to do the marathon of becoming great. Passion runs hot and burns out, while people with purpose—think of it as passion combined with reason—are more dedicated and have control over their direction. There is a great line from Goethe as well: “Absolute activity, of whatever kind, ultimately leads to bankruptcy.” The inventor of the Segway was passionate. Better to have clear-headed purpose.

28. Use Everything Around You — Make use of Seinfeld’s question: “I’m never not working on material. Every second of my existence, I am thinking, ‘Can I do something with that?’” Seek the lessons in everything, every day and apply it to your work.

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As I said in the introduction, we must pay attention to the greats in any field and derive the principles and lessons from their work and apply to our own paths. If you want some more routines from great writers and artists, check out WritingRoutines.com.