10 principles learned from Ryan Holiday on making work that lasts

[…] anyone doing any kind of creative work is attempting to do just that: to have impact and to survive. – Ryan Holiday in his book, Perennial Seller

Ryan Holiday is a writer and media strategist. He was the marketing director for American Apparel at 22. While working there he learned fast how the media industry works and how easily it is to manipulate it. Later he wrote his first book about it – Trust me, I’m lying (2012) – trying to come clean and give those tactics up. He then went on to write several other books and started his own creative agency, focusing on consulting other bestselling authors.

Through his writing, he promotes the kinds of life and work principles that most people don’t want to hear about. The kinds that are more difficult to follow or to grasp. And this lands us to one of his other books – Perennial Seller (2017) – the art of making and marketing work that lasts.

While most focus on following every trend, doing what everyone else is doing because ”that’s what you do”, jumping on every flashy opportunity (and losing sight of the big picture) in hopes of succeeding, in Perennial Seller we learn that this type of thinking won’t get us anywhere special, not on the long run.

  • How did The Shawshank Redemption fail at the box office but went on to gross more than $100 million as a cult classic?
  • How did The 48 Laws of Power miss the bestseller lists for more than a decade and still sell more than a million copies?
  • How is Iron Maiden still filling stadiums worldwide without radio or TV exposure 40 years after the band was founded?

The book lists all of the principles and steps in creating work that matters. Along with stories about why and how the greatest products ever made are still alive years after their creators are gone or since their first day into the world – books, movies, bands and even restaurants or other businesses.

[…] classics stay classic and become more so over time. Think of it as compound interest for creative work. […] That’s the dream. To matter, to reach, to last. – Ryan Holiday

1. We need to have a purpose.

That purpose will keep us going when things get tough. When we’ll want to give up. When others we’ll tell us to give up. It will be the reason to get up in the morning. And the one not letting us go to sleep. To start with why. The answer to this question will determine how much we’ll invest in our idea. Everything else has to follow the why. The what, the how, for who and for how much. In other words, the motivation is so strong, that one can not not do it.

From sacrifice comes meaning. From struggle comes purpose. – Ryan Holiday

And the other way around.

2. Without question, we need to know who we’re making anything for.

Everyone is not an answer. We have to choose. Figuring out our target later is not an option. This we’ll mean a great deal in the second part – marketing. Only when we know who are the people we’re making anything for, we’ll be able to make the right decisions along the way. Knowing what we have to do, what we won’t do, what’s essential, what’s irrelevant, what to keep, what to toss. 

The best way I’ve found to avoid missing your target – any target – entirely is to identify a proxy from the outset, someone who represents your ideal audience, who you think about constantly throughout the creative process. – Ryan Holiday

And we must know what our work can do for people.

3. It must be our primary focus.

We can’t just hope that someday the muse will knock on the door. As the saying goes, writers write. And this is true for anyone else – musicians, designers, artists, developers. One of my former colleagues said she doesn’t understand all the hype around events for entrepreneurs talking about entrepreneurship. Entrepreneurs do.

You don’t wait to get hired on something to write. – Sarah Silverman

So many people ”want to be the noun without doing the verb” – Austin Kleon.

4. Creating work that matters can’t be done without sacrifice.

Wanting to have it all might be possible, but in average amounts on each area. This is why only a few people in history managed to last. It’s not easy, it’s not for everyone. Knowing upfront what we’re willing to sacrifice is important.

A willingness to trade off something – time, comfort, easy money, recognition – lies at the heart of every great work. – Ryan Holiday

5. We have to learn to eliminate noise.

Defined as anything and everything that doesn’t represent our main focus, commonly known as distractions. To not say ‘yes’ to everything that comes our way. To see if it fits with our vision first. Not just following quick wins and money. When an idea gets lots of attention, usually everybody wants on board, to not feel left out.

These are precisely the opportunities to avoid. First off, there’s too much competition. Second, the hype obscures whether there is the realistic long-term potential […]. – Peter Thiel

For some examples just look at The Museum of Failure. 😉

6. We have to choose our competition.

Yes, we can do that. Not the other way around. When we create something, we’re not only competing with what’s being done today, we’re competing for attention with every piece of work that’s ever been made. If we look at which works sell today, we can notice that some of the greatest ever created are still on the roll and keep going for tens and hundreds of years.

If you listen to the greatest music ever made, that would be a better way 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. – Rick Rubin

7. We’re looking for timeless, not timely.

We’re talking about work that will stand the test of time. We need to capture what’s timeless even about timely events.

Focus on the things that don’t change. – Jeff Bezos

8. Rushing won’t get us anywhere.

We can’t rush into something on our way to the next ”big thing”, like checking off tasks on some to-do list. We’re here for the longest run possible, not the sprint competition.

Whether a really good book is finished a year earlier or a year later makes no difference. – Stefan Zweig

To make our pursuit, our idea work, we need to understand it inside-out. We have to know how it will fit into context, into the bigger picture, the world, and our purpose.

He’d lock himself in a room, pull the blinds, and tune everything out. He’d look forward and inward and outward and just think. […] he’d spend weeks just looking at an idea, testing whether others had already come up with it, identifying possible problems with it. Only after this period ended would he begin the real work on the project. – Ryan Holiday about Frank Lucas

Something that today is only a luxury for most. Business owners want everything done yesterday. But without any time to fully analyze a problem, the solutions will be superficial.

9. Ideas have no value.

First, if we still think that sharing our idea means that someone else will do it before we get the chance, we’re forgetting one simple fact. Most people don’t want to go through the struggle of doing anything difficult. Most just like the idea of owning the results, taking selfies at the finish line.

Second, when we’re serious, when we really just want to make the best possible product, we can’t just stop when someone else is working on the same idea. If you want to open a coffee shop, don’t look for an area where there are none, launch right next to an already existing one. We don’t know how serious or capable they are. They might not be as good as we are. But how do we know if we’re any good at what we’re doing? 

10. Asking, listening, redoing is part of the creative process.

First, ”creating is often a solitary experience. Yet work made entirely in isolation is usually doomed to remain lonely”.

You don’t have to be a genius to make genius – you just have to have small moments of brilliance and edit out the boring stuff. – Anne Lamott

Second, ”creative people naturally produce false positives. Ideas that they think are good but aren’t”.

The key is to catch them early. And the only way to do that is by doing the work at least partly in front of an audience. A book should be an article before it’s a book, and a dinner conversation before it’s an article. – Ryan Holiday

To be clear, this list ended, but it’s not even close to all the points made in the book. It’s not easy work. If it would, everyone could do it.

The next chapters from the book deal with the more detailed aspects of marketing. If creating something that matters for other people, that will last forever is something on your mind, Ryan Holiday says that ”like every magic trick there is a method behind it”. Learn it from his book.

Resources and further reading

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