4 Lessons from Perennial Seller by Ryan Holiday

There is one book that has provided me with the most insight when it comes to both creating stories as well as finding an audience for them: Perennial Seller by Ryan Holiday.

I will share the lessons I’ve learned, tested and applied along the structure of the book. Which, hopefully, you can apply to your writing as well (assuming you are a writer). Naturally, I recommend to read the book, it’s gold. Whether you are a writer, entrepreneur, musician, painter, anything.

Spoiler alert: the tactics described in the book really work! I’ve used them to approach Ryan Holiday himself – and I got a reply with some valuable advice. I’ve applied this, and it is already starting to bear its fruit. But more on that later.

These are the lessons that I’ve learned in the past eight months while working on my website turnerstories.com. About creating my short fictions stories and, later, my blogposts and podcast. How I am trying to position my website and my work in different ways. Always tweaking and pivoting to see what works. Once the work is published online, it only just begins. Then there’s marketing and promoting the work. Coming from an entrepreneurial background, with a particular focus on marketing, I love this piece of the process almost as much as creating itself. Luckily, I have to say, for I can imagine not every creator is eager or comfortable marketing their product. However, I’m sure that when these people read Perennial Seller, they will be very pleased with the approach and ideas presented. Holiday can really guide you through this. The last part in the process, but by no means the final part, is building your platform. 


#1: The creative process

According to Ryan, the creative process is the most important part of creating something perennial. Whether it is a book, a movie, a painting or a business. 

He states that the work you produce must be so good that people recommend it to their friends. To be honest I still find this difficult, how can you determine that your own work is good enough to create positive feedback and word of mouth? First, you must be really pleased with the work yourself. Really pleased. Then, you have to let others read it. Be it your spouse, family, friends, editor(s) – if you’re lucky. Have at least 5 people read it and ask for their honest feedback and suggestions (you’ll know who to ask, your most critical friends of course, preferably avid readers).

© Alice Achterhof

© Alice Achterhof


Your writing purpose
What is your purpose to write? In other words, why are you creating? Again, not easy. Eventually I understood that I want to write short stories to understand the world we’re living in better, and to understand the future we’re heading towards. In addition, I want to learn more about what it means to be human. I aim to use the stories as mirrors for myself and others. To reflect on our shared human experience.

Don’t be afraid to be controversial, or stand out. Try to break new ground, and own it. If you feel (a bit) scared about what you have produced, you might me on to something.

“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.” – Ryan Holiday on creating perennial work.


Who is your audience?
With this in mind, the next step is to determine who your audience is. Admittedly, for me this has been (and still is) the hardest part. Why? Because you can have a vague idea when you start out, but you’ll never know who will like your work when you put it out there. 

I secretly still believe my stories can relate to anyone. However, this is folly. If you think like this, you have no idea how to reach people. Targeting everyone is basically targeting no one. So, what helped me? Well, I predominantly write somewhat dystopian fairy tales. What else is out there that’s similar to that? Black Mirror, the TV-show is a starting point. Who watches this? Or short fairy tales written by Ransom Riggs, the Brother’s Grimm, J.K. Rowling to name a few. Who reads this? Start from there. Find similar art. Find out who likes those art forms. 

Another great piece of advice, originally from Kurt Vonnegut: write to please just one person. 


Let your work simmer
So, now you’ll find yourself creating, with intent. It sounds so simple. But it never is. I for one have never had a day in which I was able to produce a full short story – perfectly written. Probably no one has achieved this. And rightly so. You’ll need “space time”, you need to let your work rest. What happens to me when I do this, is that the story simmers. It’s always there subconsciously. And then, during a conversation, watching TV, commuting, in bed or when I have a walk, something usually clicks and I jot down ideas in my Notes app (find out more about my note taking strategy). 

I typically write one short story in about 2-3 weeks. I used to be faster, but I have a full-time job, and I started to write these blogposts as well. Oh, I decided it would be fun to launch a podcast with my stories… Time is both my friend and enemy.

You have to make sure people actually read your work as well! To create perennial work is different than trying to create viral work and instant success. That rarely happens. Plus, virality may be great, but you should be careful it doesn’t lead to obscurity. I mean, you’d like your work to be read still in ten years’ time, right?


#2: Positioning your writing

All responsibility and leadership falls onto you, as a creator, Ryan states. And its true. It doesn’t end with just creating. You have to be able to build a website (or have the funds to have someone else do it, but with services like Squarespace, that’s not necessary). 

You have to be a marketer and reach out to other blogs and platforms, you have to set up social media accounts and post interesting content, you need to find fans. You are the CEO of your work, you have to treat your writing like a business.


Find an editor
When I finish the first draft of any story, I send it to a couple of people who either have experience with editing (professionally) or are avid readers like me. All of them provide me with incomparable feedback, resulting in my stories getting better, having more depth or just help eliminate spelling, grammar and continuity errors. 
In the book, Ryan urges you to have an editor, to submit your work to them. Because, naturally you haven’t finished when you completed your first draft. Then the sculpting begins.

“No one creates flawless first drafts. And nobody creates better second drafts without the intervention of someone else. Nobody.” – Ryan Holiday on the importance of having an editor.

But if you just start out, you might not be able to afford a professional editor. (Just like me). Reach out to people you know, people who can give you good and honest feedback.


Your pitch
What do you say when someone asks you what your writing is about? Have you thought about your “pitch”? It is vital that you try to determine who you are aiming for. It goes hand in hand with determining who your audience is. But now you make it more concrete, like a description. Who is the intended audience then? Like I said before, I found this most difficult. So I started comparing my work to what is already known. So in one sentence, people have an idea what kind of stories I write. Ryan argues: consider how someone would describe your book, movie, restaurant, campaign, candidacy – whatever – at a party. For me this became: “My stories can be described as a mix between the TV show Black Mirror and fairy tales by the Brothers Grimm.” So essentially it comes down to dystopian fairy tales. 


Writing goals
One last essential element in the positioning part of the book is about your goals for your writing. Why are you doing this? What do you want to achieve? In terms of creating a perennial seller it should be something along the lines of creating work with a lasting impact and relevance. Of course it is difficult to say whether I have done this. Time will tell. Inherently, fairy tales contain lessons or parables. Usually these parables can speak to any generation. I mean, the fairy tales of the Brothers Grimm have stood the test of time. 

Next to that, setting goals in general as to what you want to achieve with your writing is crucial, for it makes to think about the steps you need to take to get there. A goal could be to get a publishing deal, to be able to earn money with doing something you absolutely love, to get featured in a particular magazine. What is your goal? 


#3: Marketing your work – finding readers

“If you don’t see any salespeople, you’re the salesperson.” – Peter Thiel

Yup, you are. So you better use all the hustle you have. And when you read Perennial Seller, you are a lot more likely to be the salesperson you are required to be. 


Attracting readers
You want people to read your work. But how to attract readers? In the marketing part of the book, Holiday expands on many different ways to get your work in front of others. One of the most important elements to achieve this, is to create word of mouth. 

To begin, take inventory of everything you have at your disposal:

  • Relationships: professional, personal, familial

  • Media contacts

  • Research form past launches of similar books/platforms and use what worked

  • Resources or allies (other bloggers)

  • If applicable: an advertising budget

Tell them about your work. Establish relationships. Make sure your work is easily accessible. How much will it cost people in terms of time and money? He suggests providing your work for free (at least in the beginning) and make it easy to get by.

The more accessible your work is, the easier it will be to market. First you need to create an audience and turn them into fans. Money comes later. (Options to monetize your work later are using a service such as patreon.com, setting up a PayPal donate button, publishing a beautiful eBook on Amazon, contributing to sites like medium.com, etc.).


Drawing in influencers
It’s not easy asking for a favor to someone you know, the next part is even harder. Asking for a favor to someone you don’t know – yet. 

The internet is full of them, influencers, other people with bigger platforms than you have, usually directed towards a particular subject. Who do you admire in your field? Or maybe even in other fields. Your work might complement their message.

After you have created the best work you’re capable of, you have to reach out to others to help you gain traction to your blog. In Perennial Seller, many useful tips are shared in order to do this (which I used to get a reply from Ryan Holiday himself):

  • Research into the influencers you want to approach. Ideally, they influence you already. If they don’t, dive in. Who has a big following in the field you’re aiming for? Who seems to have a hunger for content that you produce? Who is regarded as a trendsetter?

  • In making the ask, it is best not to ask for the thing your want directly. Establish a relationship. Talk about how they have inspired you (to do what you do).

  • Be a human being. Be genuine.

  • Don’t go where everyone else is going. Find the people who aren’t besieged by requests.

  • Make it about how your work makes the influencer look good to their fans.

  • Most people with platforms provide non fictional work on their blogs. Sometimes I found that a message in one of my stories perfectly complemented theirs’. I pointed this out and some people really liked that idea. For instance, my story The Money Tree, resonated well with followers of debt and financial management blogs.


#4: Building your writing platform

There is a popular theory, developed by Kevin Kelly, that a creator needs 1,000 true fans in order to make a living. True fans are people who would buy anything you produce. If you’ll be consistent in providing regular content, you could make a living this way. In general, I think the article is essential in understanding marketing.

“A platform is the combination of tools, relationships, access, and audience that you have to bear on spreading your creative work.” – Ryan Holiday

According to Holiday your platform consists of: your website, social media channels, your friends, influencers who appreciate what you do, media outlets, the community your work exists in, your email list (for tips on growing your email list I recommend checking out Pat Flynn, Sumome, and tips shared in the book itself) and much more. 

A platform is something you must seek to continuously feed with your creative work and effort to get it under people’s attention. It’s something you must control and nourish yourself. It is the most important thing you have in communicating with your audience.


Your social media presence
Managing your social media accounts can be fun, but requires a lot of time – and skills! Photoshopping the right images, staying in touch with fans and influencers, following interesting people/accounts, testing the response to your posts, etc.

Not every channel may work, although things can change. Figure out which channel best fits your work. For me Instagram works the best in terms of forwarding people to my website and content response, followed by Twitter. Facebook has proven to be more difficult.


Relationship management
You have to invest in your network of relationships, contacts and influencers. Holiday advices you to be generous, do favors and help others with their products. It’s all about developing a relationship and offering value. Then, hopefully, the favor will be returned one day. 

The most important relationship described in the book is the one with your fans. What your fans think and want is the most important thing. And you should serve them well.


Building a body of work
Building a platform takes a lot of time and dedication. A lot. People need to hear about you multiple times and from different angles, before they are willing to give your work a look.

Success requires an unstoppable author. You must continue to produce work. Then market it. Keep in touch with your relationships. And again, and again. 

“The best marketing you can do for your book is start writing the next one” – Ryan Holiday on building a body of work.


Using the tactics learned to get additional advice from Ryan himself

As you’ve seen earlier, I tried to incorporate the tactics taught in Perennial Seller, to approach Ryan himself. And it WORKED! I got a response to the question I posed in the mail: I have a question, if you would be in my position what are the first few things you would do to reach 250.000 people in a year with my site?



Immediately, I sought to follow his advice. I turned to put my work on medium.com, Reddit, Thrive Global, and I recently launched a podcast as an anthology series of my stories. Ideal if you’re commuting, to listen to a short fiction story of about 25-35 minutes. (Find the podcast here.) 

I started out writing solely fictional stories. With these blogposts, I entered the non fiction arena as well. With these posts I seek to describe my writing journey and the lessons I’ve been learning while doing it.


Perennial Seller has provided me with a map that I can use to find my writing destination. My dream of publishing my stories and novels worldwide, that I can live off my writing. It isn’t a one-day walk, nor do I expect it to be. But the directions Ryan Holiday provides, get me one step closer every day, week and month. 

So, whatever you want to write about, Perennial Seller will be an excellent companion on your journey towards your writing goals. Especially if the hustle of marketing your creative work seems daunting.

Write. Publish. Market. Repeat.



Disclaimer: some links in the text above refer to Amazon. Those are affiliate links and if you would buy something, I receive a small commission. Feel free to choose another retailer or not use the link. I incorporated it, because I need to even out the costs of hosting my site and I don’t want advertisements on the site :-).