It’s a Keeper: The Art of Creating Timeless Work

In late 1997, Jerry Seinfeld had a decision to make: produce a 10th season of his eponymous show, or call it quits.

NBC had just offered him $5 million per episode, more than three times what any network had offered any television personality in the past, and over 100 times what he’d made in the early seasons.

Yet he turned them down.

Was it a smart move? In the digital era, that kind of decision can be hard to fathom. The sense of immediacy that has guided content creation over the last decade would lead many artists to accepting such a deal. $100 million is a lot of money for anyone.

Today, Seinfeld makes an estimated $400 million a year in royalties for his role as an actor and executive producer of the show.

The figure might seem staggeringly high, but those who have studied how the entertainment industry’s wealthiest make their money will find it unsurprising.

It’s not the viral content that makes the money. Nor is it the content aimed at targeting trends. It’s the work that stands the test of time.

Prince knew it. That’s why he fought so vehemently to protect his copyright.

Ted Turner knew it. That’s why he bought MGM studios, only to sell it back, but hold onto the film rights. The value was in the content, not the brand.

Ryan Holiday knows it too. The 30 year-old Director of Marketing for American Apparel and New York Observer editor is also a successful writer, penning five non-fiction books over the last five years.

In a recent article entitled Forget Going Viral. Here’s How To Create Work That Lasts Forever, Holiday went into unprecedented depth to explain his strategy for creating timeless work, and it stands in opposition to everything defining modern content creation.

Holiday advocates for building slowly and steadily in order to demonstrate value. Doing so takes discipline, especially when critics start branding artists failures when they choose not to make meteoric leaps forward with every project.

This criticism has leeched into, and subsequently subverted, the upper echelon of management and distribution in the entertainment industry over the recent years. After a slew of indie film directors made a successful transition into blockbusters, untested filmmakers found themselves thrust into projects with nine-figure budgets and inflated expectations. For every Patty Jenkins and Wonder Woman there are two or three Josh Tranks and Fantastic Fours – talented creators who find themselves over their heads, and may never work on big projects again as a result.

In contrast, Holiday knew it would take several books before his experience and reputation would lead to the trust of both his publisher and audience, as well as the success he deserved. When it did come, he was ready.

“My first book, Trust Me, I’m Lying, got relatively little support from my publisher because I was an unproven author, but by the time my third book, The Obstacle Is the Way, came out, I started getting more attention. By my fourth and fifth books, I had a strong enough track record that I began to get strong retail placement and larger marketing budgets. Now with my sixth book, Perennial Seller, I’m able to write my own ticket marketing-wise, they want to keep me happy, rather than the other way around.”

It’s the ideal result, one that most artists aim for: autonomy. The state in which excellence can fully flourish.

While the decision over whether something is truly timeless ultimately rests on its audience, Holiday’s strategy sets the best foundation for making it possible.

Of course, even reaching that point takes time, commitment, and a whole lot of work. So get to it.

Read Ryan Holiday’s full breakdown of his strategy here.

Seriously, do it. It’s not just an insightful read for writers, but anyone looking to ensure their work stands strong forever.

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