Perennial Seller by Ryan Holiday: Notes21 min read

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I love Ryan’s work. And I’ve read many of his books (see below). But I was compelled to read Perennial Seller after Ahref’s Head of Marketing, Tim Soulo, recommended it in his course, Blogging for Business (notes available in my commonplace book).

While I enjoyed it I felt there could have been more for the reader to act on. I understand Ryan’s decision to focus on principles in an effort to write a timeless book, but it would have been nice to know what to do other than “create great work.”

For more on why things catch on, I recommend reading Jonah Berger wonderful book Contagious.

The Five Big Ideas

Make creating great work your primary focus.

Be a verb rather than a noun (in other words, make creating a “need” rather than a “want”).

“The Dip” is inevitable in any creative endeavor.

Nobody creates better second drafts without the intervention of someone else (e.g. an editor).

The best marketing you can do for your book is to start writing the next one.

Perennial Seller Summary


In every industry, certain creations can be described as “perennial.” By that Ryan means that, regardless of how well they may have done at their release or the scale of audience they have reached, these products have found continued success and more customers over time.            

Part I: The Creative Process

Derek Halpern says you need to “create content 20% of the time. Spend the other 80% of the time promoting what you created.” Ryan makes an interesting counter argument,

The kind of important, lasting work we are striving for is different—we’re talking about making something that doesn’t rely on hype or manipulative sales tactics. Because those methods aren’t sustainable. And they do an injustice to great work.            

Ryan on creating great work,

To be great, one must make great work, and making great work is incredibly hard. It must be our primary focus. We must set out, from the beginning, with complete and total commitment to the idea that our best chance of success starts during the creative process.              

Austin Kleon says, “Lots of people 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.” (Sam’s note: Austin has a wonderful book on creativity called, Show Your Work which I highly recommend.)            

“You must have a reason—a purpose—for why you want the outcome and why you’re willing to do the work to get it. That purpose can be almost anything, but it has to be there.” (Sam’s note: This echoes Simon Sinek’s thesis in Start with Why).

Ask yourself,

Why are you creating?

Why are you putting pen to paper and subjecting yourself to all the difficulties you will certainly face along the way?

What is your motivation?

“If you’re to create something powerful and important, you must at the very least be driven by an equally powerful inner force. If there is anything to romanticize about art, it’s the struggle and the dedication required to get it right—and the motivating force that makes it all possible.”               

“In the course of creating your work, you are going to be forced to ask yourself: What am I willing to sacrifice in order to do it? Will I give up X, Y, Z? A willingness to trade off something—time, comfort, easy money, recognition—lies at the heart of every great work. Sometimes more, sometimes less, but always a significant sacrifice that needs to happen. If it didn’t, everyone would do it.”                

Ryan’s analogy for creating art,

“Art is the kind of marathon where you cross the finish line and instead of getting a medal placed around your neck, the volunteers roughly grab you by the shoulders and walk you over to the starting line of another marathon.               

There is inevitably a crisis and a low point in every creative work. You will run into what author and marketer Seth Godin calls “the Dip.” The existential crisis where you’ll have to ask yourself: Is this even worth it anymore?

Ryan on creating work that matters,

Creating something that lives—that can change the world and continue doing so for decades—requires not just a reverence for the craft and a respect for the medium, but real patience for the process itself. By patience, I’m not referring just to the amount of time that creation will take, but also the long view with which you evaluate your own work. And the long view can be really long.

Ryan on creativity,               

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.

The risk for any creator is over-accounting for what’s happening right in front of them.               

“The best we can do is sit down and create something, anything, and let the process organically unfold. Tolerating ambiguity, frustration, and changes in the grand plan and being open to new experiences are essential to creative work. Indeed, they are what makes creativity work.”—Scott Barry Kaufman

Holding multiple contradictory ideas in your head at the same time is an essential phase of creativity. (John Keats called it “negative capability”). You have to be able to tolerate this and then refine your idea like mad until it gets better.               

“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.”    

“An audience isn’t a target that you happen to bump into; instead, it must be explicitly scoped and sighted in. It must be chosen.”

There is a small publisher whose slogan is “Find your niche and scratch it!”               

“Successfully finding and “scratching” a niche requires asking and answering a question that very few creators seem to do: Who is this thing for?”               

“For any project, you must know what you are doing—and what you are not doing. You must also know who you are doing it for—and who you are not doing it for—to be able to say: THIS and for THESE PEOPLE.”

The best way Ryan’s 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 then think about constantly throughout the creative process.               

“Just as we should ask “Who is this for?” we must also ask “What does this do?” A critical test of any product: Does it have a purpose? Does it add value to the world? How will it improve the lives of the people who buy it?” 

One of the best pieces of advice Ryan received as a creator was from a successful writer who told him that the key to success in nonfiction was that the work should be either “very entertaining” or “extremely practical.”               

“You want what you’re making to do something for people, to help them do something—and have that be why they will talk about it and tell other people about it.”              

“The bigger and more painful the problem you solve, the better its cultural hook, and the more important and more lucrative your attempt to address it can be.”

Ask yourself,               

What does this teach?

What does this solve?

How am I entertaining?

What am I giving?

What are we offering?

What are we sharing?

What are these people going to be paying for?

“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).”               

Goethe observed that the most original artworks “are not rated as such because they produce something new” but because they are saying something “as though it had never been said before.”               

The higher and more exciting standard for every project should force you to ask questions like this:

What sacred cows am I slaying?

What dominant institution am I displacing?

What groups am I disrupting?

What people am I pissing off?

“You cannot violate every single convention simultaneously, nor should you do it simply for its own sake. In fact, to be properly controversial—as opposed to incomprehensible—you must have obsessively studied your genre or industry to a degree that you know which boundaries to push and which to respect.”               

“You want to provoke a reaction—it’s a sign you’re forging ahead.”

“Your work may shock people, they might not be willing to accept it right away—but that’s also a sign that you’ve created something fresh and truly original.”               

“Deep, complex work is built through a relentless, repetitive process of revisitation.”               

“Ignore what other people are doing. Ignore what’s going on around you. There is no competition. There is no objective benchmark to hit. There is simply the best that you can do—that’s all that matters.”

“It takes time and effort and sacrifice to make something that lasts.”

Part II: Positioning

The first wake-up call for every aspiring perennial seller must be that there is no publisher or angel investor or producer who can magically handle all the stuff you don’t want to handle.               

Perennial sellers are made by indefatigable artists who, instead of handing off their manuscripts to nonexistent caretakers—“kissing it up to God,” to use a Hollywood expression—see every part of the process as their responsibility. They take control of their own fate. Not simply as artists but as makers and managers.               

Instead, prior to release, considerable effort needs to be spent polishing, improving, and, most critically, positioning your project so that it has a real chance of resonating with its intended audience.

We have to take this thing that means so much to us and make sure that it is primed to mean something to other people too for generations to come. That it will stand out among a crowded field of other creators sincerely attempting to do the exact same thing. That it will be the best that it is capable of being and that the audience it is intended for is primed to love it. And the best person in the world to accomplish this difficult task? You.                

The competitive landscape for creating something that lasts is not one for the entitled or the half committed.               

Once you understand that this project’s chances of success or failure rest entirely on you, you must undertake a paradoxical and difficult task: finding and submitting your work to the feedback of a trusted outside voice (or, in some cases, voices).               

But ultimately, to take a project where it needs to go, you’ll need to rely on an editor to help you get there.               

As infuriating as it may be, we must be rational and fair about our own work.               

Ask yourself: What are the chances that I’m right and everyone else in the world is wrong? We’ll be better off at least considering why other people have concerns, because the reality is, the truth is almost always somewhere in the middle.               

“Remember: When people tell you something’s wrong or doesn’t work for them, they are almost always right. When they tell you exactly what they think is wrong and how to fix it, they are almost always wrong.”—Neil Gaiman

Getting feedback requires humility. It demands that you subordinate your thoughts about your project and your love for it and entertain the idea that someone else might have a valuable thing or two to add.

Nobody creates flawless first drafts. And nobody creates better second drafts without the intervention of someone else. Nobody.   

Sometime after the bulk of the creative production is done but before a work is fully wrapped up, a creator must step back and ask: “OK, what was I trying to make here? Did I get there? What do I need to change or fix in order to successfully do so?”              

A similar exercise that I like to do with all my projects is one I call “One Sentence, One Paragraph, One Page.” It goes like this: Put the website or the beta version of your app or your manuscript aside and grab a piece of paper or open a blank Word document. Then, with fresh eyes, attempt to write out exactly what your project is supposed to be and to do in … One sentence. One paragraph. One page. This is a ______ that does ______. This helps people ______.               

When you know what genre you’re in and you know what you’re trying to accomplish, it becomes clearer which decisions matter and which don’t.               

You say to them: “Here’s what I’ve been aiming for. Do you think I am close? What do I need to change with my [writing, design, music, art, etc.] to get where I’m trying to go?”               

Regardless, you must start somewhere—ideally somewhere quantifiable. By which I mean: 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?               

With a concrete number in mind, it’s a lot easier to establish and empathize with what your audience is going to need.               

You must create room for the audience to inhabit and relate to the work. You must avoid the trap of making this about you—because, remember, you won’t be the one buying it.               

Today, in order to even have a chance at people’s attention, your project has to seem as good as or better than all the others.          

Three critical variables determine whether that will happen:               

Positioning is what your project is and who it is for.

Packaging is what it looks like and what it’s called.

The Pitch is the sell—how the project is described and what it offers to the audience.

Work that is going to sell and sell must appear as good as, or better than, the best stuff out there. Because that’s who you’re competing with: not the other stuff being released right now, but everything that came before you.         

That’s why it’s critical that you be able not only to clearly and concisely explain who and what you are, but also to show it, too.       

If your goal is to create a perennial seller, you can’t measure yourself against people who aren’t aiming for the same thing—you can’t be endlessly checking industry charts or lists, and you can’t be distracted by the trends and fancies of other creators who are hopelessly lost.              

Knowing what your goal is—having that crystal clear—allows you to know when to follow conventional wisdom and when to say “Screw it.”

Part III: Marketing

“Marketing is your job. It can’t be passed on to someone else.”

“The mark of a future perennial seller is a creator who doesn’t believe he is God’s gift to the world, but instead thinks he has created something of value and is excited and dedicated to get it out there.”

“No one has the steam or the resources to actively market something for more than a short period of time, so if a product is going to sell forever, it must have strong word of mouth. It must drive its own adoption. Over the long haul, this is the only thing that lasts.”

“The strategy of perennial success is about trying to create work and products that will sell over the long term, but ideally we also want to sell in the short term.”               

“Selling in perpetuity and launching strong are not mutually exclusive.”               

“The first thing anyone planning a launch has to do is sit down and take inventory of everything they have at their disposal that might be used to get this product in people’s hands.”               

“As creators, we have to get more comfortable with giving people a taste of our work—or, in some cases, giving some people the entire meal for free. That’s how we build an audience and gather momentum.”               

What is the right price to create a perennial seller? Ryan’s answer is “as cheap as possible without damaging the perception of your product.”               

One of the best ways to build a readership, viewership, listenership, user base, or customer base early on is by making it cheap.

According to Amazon’s data, the cheaper a book is, the more copies it sells (and, counterintuitively, makes more money than if it were expensive).               

As a general rule, the more accessible you can make your product, the easier it will be to market. You can always raise the price later after you’ve built an audience.               

“Try to find the people least likely to get a request from someone like you, and approach them first, instead of going where everyone else is going.”               

“The most newsworthy thing to do is usually the one you’re most afraid of.”               

Don’t be afraid of pissing people off either. (Sam’s note: As Dan Kennedy says, “If you haven’t offended someone by noon each day, then you’re not marketing hard enough.”)               

Publicity is about temporarily breaking through the noise and contributing to the word of mouth that a product eventually needs to succeed.               

“Advertising can add fuel to a fire, but rarely is it sufficient to start one.”               

When it comes to creating a perennial seller, the principle to never lose sight of is simple: Create word of mouth.  

Part IV: Platform               

Becoming a perennial seller requires more than just releasing a project into the world. It requires developing a career.         

In Ryan’s definition, a platform is the combination of the tools, relationships, access, and audience that you have to bear on spreading your creative work—not just once, but over the course of a career.

“Creating a perennial seller and word of mouth is possible when you have high-level supporters who are willing to evangelize what you do and bring other people to your work.”            

“If you want people to consume your work and to know what you do next, you have to make it possible for them to hear about it as easily and regularly as possible.”

The best marketing you can do for your book is to start writing the next one.

Ryan on achieving mastery,

It’s not enough to make one great work. You should try to make a lot of it. Very few of us can afford to abandon our gift after our first attempt, convinced that our legacy is secured. Nor should we. We should prove to the world and to ourselves that we can do it again … and again.

“One of the things all creatives must do during their downtime is explore new ways of reaching new fans.”               

A great example of profiting from haters: Colonel Parker, the infamous manager of Elvis Presley, came up with the idea to sell “I Hate Elvis” memorabilia so that Elvis could profit from his haters too.

Other Books by Ryan Holiday

The Daily Stoic

Ego Is the Enemy

The Obstacle Is the Way

Recommended Reading

If you like Perennial Seller, you may also enjoy the following books:

The 22 Immutable Laws of Marketing by Al Ries

Contagious by Jonah Berger

Predictably Irrational by Dan Ariely

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