22 Rules for Creating Work That Stands the Test of Time

Ryan Holiday
9 min readMay 28, 2018

Very few of us sit down to create art or work they hope will disappear. Whether you’re an entrepreneur, a writer, a designer, a journalist, a producer, a filmmaker, a comedian, a blogger, an actor, a whatever, the whole point is to make something meaningful, something that lasts. To make something “imperishable,” to achieve, as a translator once said of Aleksander Solzhenitsyn’s work, a certain “changeless freshness.”

Yet so often this fails to happen. It is not a stretch to say that the lives of most creative works are greedy, faddish and short.

Does it really need to be that way? Or are there rules and principles to follow that increase our chances of enduring and surviving — to become an elusive perennial seller? I think there is, and I’ve written extensively on the topic (including a book with the same title, which I suggest you check out). Here, as best as I understand it, are some rules for standing the test of time.

[*] It Starts By Wanting to Create a Classic — Where do we properly begin our pursuit of a perennial seller? As my mentor Robert Greene put it, “It starts by wanting to create a classic.” You don’t do this by accident. The intention must be clear from the beginning.

[*] Remember, Ideas Are Cheap — An aspiring creator once wrote to the filmmaker Casey Neistat about whether he could pitch him about an idea he had. Casey’s response was swift and brutally honest: “I don’t want to hear your idea,” he said. “The idea is the easy part.” The difference between a great work and an idea for a great work is all the sweat, time, effort, and agony that go into engaging that idea and turning it into something real.

[*] Don’t Talk About The Work, Do The Work — “Lots of people,” as the poet and designer Austin Kleon puts it, “want to be the noun without doing the verb.” To make something great, what’s required is need. As in, I need to do this. I have to. I can’t not.

[*] Endure The Marathon — Take the construction on La Sagrada Família in Barcelona, which broke ground in 1882 yet whose completion is slated for 2026 — the hundred-year anniversary of the architect’s death. The months and years and decades fall away. Matthew Weiner worked on the script for Mad Men on the side for years, referring to it as his mistress, yet finishing it was not the end — or even the halfway point — because no one wanted the show. So he literally carried it with him in a bag for years, watching it get critiqued and rejected time and again. Making a classic is a marathon, not a sprint.

[*] It Can’t Be Hurried — “Literature is a wonderful profession,” a wiser and older friend once explained patiently to the aspiring novelist, Stefan Zweig, “because haste is no part of it. Whether a really good book is finished a year earlier or a year later makes no difference.” Art can’t be hurried. It must be allowed to take its course. It must be given its space — and can’t be rushed or checked off a to-do list on the way to something else.

[*] Push Through “The Dip” — There is inevitably a crisis and a low point in every creative work. We all run smack into what author and marketer Seth Godin calls “the Dip.” The existential crisis where we’ll have to ask ourselves: Is this even worth it anymore? And it won’t be the desire to get rich or famous that drives us out of that valley of despair — it will need to be something deeper and more meaningful.

[*] The Journey Will Not Be Fun — Elon Musk has compared starting a company to “eating glass and staring into the abyss of death.” There’s no shame in walking away if fun is all you’re after. Zappos and Amazon offer to pay employees to quit their job at the end of a ninety-day trial period. Why? Because not everyone is right for this life — and it’s better to realize that sooner than later.

[*] Seek Inspiration In the Greats — 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.’ It’s stepping back and looking at a bigger picture than what’s going on at the moment.” He also urges them not to constrain themselves simply to their medium for inspiration — you might be better off drawing inspiration from the world’s greatest museums than, say, finding it in the current Billboard charts.

[*] Become a Supreme Craftsman — Young aspiring writers like to point to Jack Kerouac, who supposedly wrote On the Road in a three-week drug-fueled blitz. What they leave out is the six years he spent editing and refining it until it was finally ready. As one Kerouac scholar told NPR on the book’s fiftieth anniversary, “Kerouac cultivated this myth that he was this spontaneous prose man, and that everything that he ever put down was never changed, and that’s not true. He was really a supreme craftsman, and devoted to writing and the writing process.”

[*] Patience, Patience, Patience — The old idea that “if it’s worth doing, it’s worth doing right” is at the core of great businesses. It certainly makes things a bit more intimidating, but necessarily so if lasting greatness is your intention. As Larry Page, one of the founders of Google, explained, “Even if you fail at your ambitious thing, it’s very hard to fail completely. That’s the thing people don’t get.”

[*] Test Your Work — The songwriter Max Martin, who has written for everyone from Céline Dion to Adele, subjects his nearly finished songs to something he calls the “L.A. Car Test,” where he blares the song through the stereo of a car racing up and down a beautiful stretch of the Pacific Coast Highway in Los Angeles. How does it sound? What does it add to the experience? These are the questions he asks himself during the scenic drive. Why? Because he understands that that’s what his music is for: to brighten people’s days, to invigorate their drives, and to heighten their ordinary life experiences. All work has a purpose — and it either achieves it or it doesn’t for the the audience. Don’t launch what hasn’t been tested.

[*] Go Where No One Has Gone Before — It’s hard to stand out in a space filled with giants. Listen to what the authors of Blue Ocean Strategy tell us: seek out new clear waters. Or remember Peter Thiel’s line: Competition is for losers. It’s the work that was bold and brash and new when it came out that tends to still feel fresh decades later.

[*] Obsess With Details — A master is painstakingly obsessed with the details. If you ever peer inside an Apple computer, you’ll find they’re beautiful on the inside too. The people who design them see the entire product as a work of art — as their masterpiece. They don’t cut corners, even on the parts most people will never see.

[*] Find Your ‘Editor’ — What is the important thing that writers do when they finish a draft? They hand it to an editor. An editor. Nobody creates flawless first drafts or anything. And nobody creates better second drafts without the intervention of someone else. Nobody.

[*] Every Part of the Process Matters — That saying “You can’t judge a book by its cover”? It’s total nonsense. Of course you can judge a book by its cover — that’s why books have covers. They’re designed to catch people’s attention and draw them toward the work — and away from all the other works that stand equal on the shelf. When Steve Jobs launched NeXT — his first company after Apple fired him — he spent something like $100,000 on a logo from one of the best designers in the world. Every single part and element of the process matters.

[*] Know Your ‘Why’ — Elon Musk knows that his mission is to get a human being on Mars and he believes that the future of humanity rests on it. Do you have that kind of clarity? Honestly, most of us would be well served by just one percent of that level of clarity. Your “why” doesn’t need to be public — but if you can’t define your goal for yourself, how will you know if you’ve achieved it? How will you know how to make decisions in situations where that goal is threatened or jeopardized?

[*] Take the Long View — Jeff Bezos, the founder of Amazon, reminds his employees: “Focus on the things that don’t change.” Don’t base your work on the fad of the moment, base it on something that won’t change.

[*] Be Uniquely Yourself — An essential part of making perennial, lasting work is making sure that you’re pursuing the best of your ideas and that they are ideas that only you can have (otherwise, you’re dealing with a commodity and not a classic). Don’t try to be like other people. Try to be like you. Not only will this process be more creatively satisfying, it will be better for business. Remember what Seneca said, that what’s required is “confidence in yourself and the belief that you are on the right path, and not led astray by the many tracks which cross yours of people who are hopelessly lost, though some are wandering not far from the true path.” Ignore the competition. Focus on your path.

[*] Make More Than One Thing — Good work compounds and it is the best way to increase your chances of success. Making is also marketing. Woody Allen: “If you make a lot of films occasionally a great one comes out.” You increase your chances of enduring with each shot you take.

[*] Who Is This For? — The best way to keep your ideal audience in mind is by identifying a proxy from the outset, someone who represents your ideal audience, who you then think about constantly throughout the creative process. Stephen King believes that “every novelist has a single ideal reader” so that at various points in the process he can ask, “What will ______ think about this?” (For him, it’s his wife, Tabitha.) Ask yourself: Who is buying the first one thousand copies of this thing? Who is coming in on the first day? Who is going to claim our first block of available dates? Who is buying our first production run?

[*] Build a Platform — Ideally, you have an audience to launch to. As Kevin Kelly’s 1,000 True Fans theory goes: “A creator, such as an artist, musician, photographer, craftsperson, performer, animator, designer, videomaker, or author — in other words, anyone producing works of art — needs to acquire only 1,000 True Fans to make a living.” A platform is the combination of the tools, relationships, access, and audience that you have to bear on spreading your creative work. So start building your platform now — at the very least, build your email list!

[*] Get Lucky — It would be dishonest to talk about creating a classic, perennial seller, and pretend that luck has nothing to do with it. Because luck matters a lot. No matter what we have heard from our parents, hard work does not trump all. At the very, very top, the world is not a simple meritocracy, and it never has been. As Nassim Taleb puts it, “Hard work will get you a professorship or a BMW. You need both work and luck for a Booker, a Nobel or a private jet.”

Ryan Holiday’s book Perennial Seller: The Art of Making and Marketing Work that Lasts is a meditation on the ingredients required to create classic books, businesses, and art that does more than just disappear. His writing has been translated into 30 languages and sold over a million copies worldwide while his creative firm, Brass Check, has worked with companies like Google, Taser and Amazon. You can join the 90,000 people who get his weekly articles.

This was originally published on Thought Catalog.

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Ryan Holiday

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’ http://amzn.to/24qKRWR