Before I was a writer, I was simply a reader. Like many readers, I was somewhat in awe of the process. I had no idea how the books I read were made, or how if I was beginning to then aspire to one day write one myself, how on earth I would manage to string so many words together.

The author and poet Austin Kleon has done the creative world an enormous favor with his concept of showing your work. Part of the mystique of the artistic brand is to make it look easy, effortless. The result is that creativity seems like a black box. In fact, we should show how we make what we make. To help others, to understand our own process, to practice humility. To show people that it’s not impossible to turn their ideas into work.

There was once an exchange between the painter Edgar Degas and the poet Stéphane Mallarmé. Degas was having trouble trying his hand at poetry and so he complained to his friend about his trouble writing, “I can’t manage to say what I want, and yet I’m full of ideas.” Mallarmé’s response: “It’s not with ideas, my dear Degas, that one makes verse. It’s with words.”

But still, how? I can’t answer generally, but I can show how I learned how to string words together and turn them into a book. At my wedding in early 2015, my editor made a suggestion about an idea for a book she thought I might like to kick around. As I write this article, now roughly two and half years later, that book is on its way to bookstores ready to be sold. Books, like poems, are a matter of words. And a hell of a lot of work. What I thought I would do in this article is show almost step by step, what that work is and how it happened in the creation of Perennial Seller. Given the book’s subject matter — creating artistic work that stands the test of time — I’m excited to share how I tried to accomplish that with my own writing. It’s going to be a long post — but that’s because books are a lot of work. Enjoy.

Part I: IDEATION

As Mallarmé was saying, ideas are cheap. Lot of people have them. Even smart people have lots of bad ones. But the truth is every project starts with an idea. They can’t start anywhere else. There would never be any creative work without an idea that came before it.

Often, a book starts with an incredibly vague idea. The original suggestion from my editor had been a book about book marketing. That is, after all, my day job. And so the project began with that idea and a short one page proposal.

As it happens, the book Perennial Seller is not a book about book marketing, but in 2015 I sure thought it would be. Doing so made a ton of sense — at that time, my company Brass Check had five different clients on the New York Times Bestseller list. I began to write the book proposal for what would become Perennial Seller in March of 2015. In fact, here is the original title (a suggestion from my agent) and subtitle I used in the book proposal:

THE NEW RULES OF BOOK PROMOTION:

Why Content and Strategy Trump Tactics Every Time or How to Succeed with Content and Strategy When All the Old Tactics No Longer Work

Taking a step back for a second, if you’re wondering what a book proposal even is, you’re not alone. In the world of nonfiction traditional publishing, most authors don’t get to simply wake up one day and sit down to write a manuscript (even when it’s their sixth book). Before an author writes a single word of the book itself he or she will write down what the idea for the book will be and why people will read (i.e. buy) it — and they have to sell that to someone. It’s like writing a business plan for a book. Proposals can contain an outline, sample chapters, endorsements from relevant tastemakers, and anything else that may attract the attention of an editor at a publishing house, with the goal usually being to secure as high of an advance as possible. A publisher essentially buys the rights to publish a future book by you based on your book proposal.

In my case, my publisher bought the rights to my book about book promotion based on the proposal I’d written. It ended up selling that same month, in March 2015.

It’s important to stress that the iterative phase of the book idea doesn’t necessarily stop once the book proposal sells. Authors frequently (maybe even usually) deliver a book that is substantially different that the book that was laid out in the original proposal. I usually tell authors that the proposal is for the publisher — the book is for themselves. So what is even the point of a proposal anyway? That’s another article for another time, but suffice it to say that even though I’d sold a book about book promotion, by May of 2015 the idea still wasn’t sitting right with me.

Around that time I happened to be reading book called Enemies of Promise by Cyril Connolly. He explored contemporary literature (from 1939) and the timeless challenges of making great art. It was also an honest self-examination of why Connolly, himself a talented writer, hadn’t broken through commercially with his previous work. In the book, Connolly throws down an ambitious gauntlet for authors: Making something that lasts for ten years.

“Contemporary books do not keep. The quality in them which makes for their success is the first to go; they turn over night.” — Cyril Connolly, Enemies of Promise

Anyway, I loved the book. Though it was clear to me that because of my track record as an author and because of my company Brass Check I could do quite well with a book marketing book (and monetize it with courses, consulting, etc), the idea just didn’t excite me. It wasn’t an idea that I thought would last. I mean, if I filled it a bunch of strategies that were working right now…who is to say they would still hold true even a year later?

I began to ask, was there enough there for something good? Would the content last? Who was even the audience for this book? Just authors? Was that a big enough, diverse enough audience? I realized something: writing a book about book marketing violated a lot my own advice about book marketing and marketing it general! I’d even written on the subject a few months before in a post for Thought Catalog titled “6 Reasons Your Book Will Fail” in which I wrote specifically about the rules I found myself on the verge of violating:

Too many books fail because it was written in a vacuum, without ever considering anything beyond your own immediate tastes and needs. You wrote without ever thinking: How the hell are people going to hear about this and why would they care if they do? You thought about why you wanted to write it, but not why anyone else needed it. […] Your book will fail because of your inflated self-importance. Do you know how many people are eagerly anticipating your book? Unless your last name is King, Lewis, Evanovich, Gladwell, Patterson, Kingsolver, Child, or R.R. Martin, the answer is next to nobody.

Such a book about book marketing would be unlikely to last — the tactics change too often, the audience was too small and I’m not sure the world actually needed another book marketing book.

As I kicked around the book some more, I remember very vividly a conversation with my writing and business partner Nils Parker. I was speaking at a conference in Puerto Rico to business executives and entrepreneurs from all over the Caribbean. It occurred to me that a book about book marketing would be too niche to ever get in front of an audience like this. Not everyone wants to write a book, after all. In the conversation, I told Nils about the Cyril Connolly quote — about lasting for ten years. His response: Now that is a better idea for a book. As we chatted, it became clear that authors were not the only people interested in making something that lasts. It’s the universal dream.

From this breakthrough, the book pivoted. Instead of being for authors it would be about authors and for everyone engaged in a creative field. It’s obvious when you think about it: Who doesn’t want to make something that sells and sells for years? Who doesn’t want to be responsible for a classic? Thus, Perennial Seller was born.

As I said, book proposals are really just the entry point to an idea. Almost every single one of my books has become something very different in the research and the writing process. In the case of my books, I scribble down my ideas and thoughts on 4x6 notecards, collecting them in big boxes, organized by theme. You can see here, where I created the notecard that would begin to serve as the basis for this book. [Note: excuse all the terrible handwriting you’re going to see in this post!]

“I want this to be

-high level

-fundamentals

-mindset driven”

“So little of what we do keep — the result is we have to produce more, market harder, sell out worse.”

“Not that books are so terrible to use as a model. Imagine a world where Homer had continuous copyright. Or Shakespeare. They’d make JK, Oprah, ALW look like they had ‘baby money.’” (that’s a Jay Z quote)

“- Can you make something that stands test of time

- Can you position/brand…

- Can you set up marketing channels…

- Can you capture a platform that…”

Ideas change. They morph. But they should be going in the right direction. Towards classic-ness timelessness, reach. That’s what I was trying to do with the idea for Perennial Seller.

Structure (What’s The Best Way To Arrange This Idea)

With the idea for the book beginning to form, the next question I had to address was how to present such a book. Think about it like this: A lawyer has their case and then they must structure their argument. Or, if you remember 9th grade, you outline your 5 paragraph essay before you start writing — not while you’re in the middle of it. A book is the same way. You have to figure out the best way to arrange and organize the information you are going to give to the reader. I always lay this out before I have written a word. I think you need to know the structure while you are researching — so you can find the material needed to best make your case.

Here’s my notecard with the structure where I first decided on the 4 part structure of Perennial Seller.

“Writing is marketing

Positioning is marketing

Marketing is marketing

Platform is marketing”

This notecard became the four sections of Perennial Seller: 1) The Creative Process, 2) Positioning, 3) Marketing, 4) Platform. The point being: I had begun this book thinking about how to teach people to market their work, and then I realized that to do a good job marketing you had to get several things right before hand, and then I realized that those things apply to more than just marketing — they apply to all creative work.

During the course of the ideation and structural brainstorming, I had essentially ditched the entire concept I had begun with. I was no longer writing the “Book Marketing Book” as my proposal had promised. I was tackling something much bigger and much more important: How to make anything last. How to make Perennial Sellers.

PART II: RESEARCH

As I explained in a video on how I wrote Ego Is the Enemy, once you have the structure, now the real research starts. I read books, articles, research papers, listen to podcasts and talks, watch documentaries and anything else I can get my hands on. (An Imgur album outlining that process can be found here.)

And I take notes on everything I read and see. I already had many hundreds of notecards about writing and creativity assembled from my research over the years. I’ve written about exactly how this notecard system works elsewhere, but at its core it’s a method taught to me by my mentor or bestselling author Robert Greene for organizing and using all of the information I read or hear, and all of the thoughts that I have. Every book I write has a dedicated box that holds every notecard that will eventually be written into the book. But I don’t only take from my books. I jot down things I like from podcasts, documentaries, conversations, and random thoughts I have.

Here’s an example of a notecard — it’s a quote by filmmaker Jon Favreau about the creative process:

“The ones that get closest to it last the longest.” — Jon Favreau (I heard this quote while listening to Favreau interviewed WTF with Marc Maron.)

All of the notecards like this one get filed into a box like the one below for when it’s time to being writing.

I do this so that I don’t ever not know what to write about. I’ve never really had “writer’s block” on a book — because I have so much material already there in the form of ideas and notes, organized in accordance with the structure. My job each morning is just expanding it into prose.

Early on in the process, I am just collecting general notecards about a project in the loose buckets of the structure. Soon enough, themes begin to emerge. For the Marketing section (on the left) we can see the headings, “Marketing is impt,” “WOM” (for Word of Mouth), “Assets,” “Free,” “Press,” and “Influences.” In another section, this time for the Platform section, we see “Platform,” “Network,” “Next book,” “List,” “Brand,” “Empire,” “Media,” “Reach,” “Long sprint,” and “1k” (for one thousand fans). The Platform headings became several of the subsections of the book, including these examples:

What’s a Platform?

Build Your List. Build Your List. Build Your List.

Your Network Is Your Net Worth

Settle In for the Long Haul

Reach Out to New Fans

Build an Empire

Above, we see a few specific notecards from the “Free” chapter of the Marketing section of the book. The one notecard on the top right about Bic ended up in the Marketing section of the final book like this:

The first Bic pen was priced at nineteen cents. A half century later, it’s roughly the same price when you adjust for inflation. Keeping the price low has made it the default pen for millions of people. Instead of running expensive celebrity ad campaigns, Bic’s marketing strategy is simply to keep its price low — and that’s not an easy thing to do.

During the research phase each story, anecdote and example that will appear in the book is transferred onto a notecard and then filed away for safe keeping until it’s time to write.

For Perennial Seller, I also conducted dozens of interviews with the very people who know the most about achieving longevity in their chosen creative endeavors. The vast majority of these interviews were conducted over email so that I could turn them into bonus materials to promote the book during the week of the launch — a lesson I learned while writing Growth Hacker Marketing. And that’s exactly what I did — you can read numerous interviews I did as research for the book as well as case studies if you email the address listed in the book.

With most of these interviews, research materials, etc. I print them out, which will have tremendous advantages for editing. It makes moving them around much easier and more efficient.

This scan shows my printed interview with Barbara Cave Henricks, which I conducted via email. Barbara is president and founder of Cave Henricks Communications, a prestigious PR firm (which has represented authors like Jack Welch and Clayton Christensen). I printed it out and marked the passages by hand. I’ve also taken one of the quotes from her first answer and physically cut it out with a scissors in order to move it to where I needed it at the time. I then transcribed the quote onto a notecard, which was used in the ‘Settle In for the Long Haul’ section of the final manuscript. She states, “I urge authors to consider how long it took them to write their books and see them published and devote at least that much time to publicizing them.” Other passages highlighted in this early interview made it into the final book as well.

The notecard containing a quote from the interview I conducted with Barbara Cave Henricks.

Part III: WRITING

At the risk of being obvious again, writing starts at the beginning — with the intro. I write in order, breaking the book up into small pieces. Writing a book is a long hard slog that can be incredibly discouraging. Progress is in short supply — the end seeming very far away. By breaking the book up in small pieces you create the illusion of progress, a sense that I am crossing stuff off the list.

Like many writers, I am prone to strange rituals. As I said, my books tend to be broken up in many small sections (I tend to have lots of short chapters instead of a few long ones). When writing these short chapters, I use separate Google Docs for each one but there comes an important inflection point in my progress, where I begin to combine these independent chapters into one Word Document. I basically go from online writing to offline editing and re-writing. (Each day I resave this Word Document in Dropbox with the acronym of the title, the phrase “working draft” and the date — so TOITW-Working-Draft-5–22.) One of the first times I start to feel optimistic about a book — Hey, this is starting to become something — is that transition from Google to Microsoft. I love looking at the file names tick the days off in Dropbox. All that is immensely pleasurable — almost as much as whatever I am saying. I am obsessed with that symmetry and progress.

Music is another ritual. I need it in the background while I write. I use the music not only to shut out outside noise but to shut off parts of my conscious mind. I’ve found that picking one song — usually something I am not proud to say I am listening to — and listening to it on repeat, over and over and over again is the best way to get into a rhythm and flow. Basically I treat the music as sort of disposable, instant flow tool. I use it until it stops working, and then I move on to the next song. I use the same song that I am writing to when I run later, or if I go for a walk. It’s just creating a continuity to the creative process.

My desk in Austin.

Another important piece of the writing phase is where to write. I do most of my writing while I sit at my desk in my office either at my place in the city or on my farm, mostly. I tend to work better at my place at the city — it has all my books and these floor to ceiling bookcases filled with them, it just feels right.

For Perennial Seller, I started the actual writing on July 13th, 2015. To me, writing is a job, a profession, and the best way to be a professional is to set professional hours. So I don’t cram, I don’t do spurts when inspiration strikes, I don’t do it in a bathrobe or from bed. I write every day and I treat it like work. I am sharpest and least imposed on in the morning so that’s when I write. I have a ritual: I get up, I shower, I get dressed as though I am going to a job and then I show up to work. I write in a journal first. I play with my son. And then I sit down and tackle whatever writing I have assigned for myself that day. I start at around 8–9 at the latest — and by 11 or 12, I am pretty much done.

But at the end of the day, it’s mostly just sitting there and stringing the words (and the notecards) together.

From that notecard, the first two paragraphs of the very first draft of the introduction to the book were written:

In 1938, the literary critic Cyril Connolly sat down to write a book that he hoped would last for ten years. In his eyes and with a world war looming in the background, this was the mark of success. Something that would last for a decade — at least.

Now, the book was reprinted and updated in 1948 and again in 2008 and here we are talking about it today. So he succeeded, and then some. Most people haven’t heard of the book — despite it’s great title, Enemies of Promise — but in his way, according to his goals, it was a success.

Six days later, that first draft was significantly beefed up and changed in Google Docs (I’d begun writing the first drafts of other sections in the meantime):

The very next day, I made further changes:

Three months into writing the book, in mid-September, I’m still working on the right wording for the intro:

Right before the manuscript went to the publisher for the first time, there was one last round of changes:

And it’s important to remember that plans change. The notecard said “Open w/ Cyril Connolly, Segue to John Fante.” Turns out I had a lot of segueing to do: The example of John Fante doesn’t appear until p. 63 of the final book, which begins Pt. 2.

A Big Moment

It also helps that I write fast. By October 15, 2015 I had a 39,000-word early draft of the manuscript for Perennial Seller to send to my editor and agent. It wasn’t yet perfect, but I was making progress. In fact, I’d made it from the beginning of the idea to the end — now I just needed to tweak and improve and re-write until I got it into publishable form (I thought this would take a few months. I did not think I would still be doing that 18 months later.)

Part IV: EDITING

If writing a book is the most difficult, the editing process is the most grueling. 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.”

What is the important thing that writers do when they finish a draft? They hand it to an editor. An editor. Not: They send it to some friends for some thoughts. Although they may get great help from friends, it’s ultimately the editor with whom writers collaborate. The industry term is illustrative: A writer submits a manuscript to an editor.

Why? Because when people are close to their own projects or their own talents, they can lose the ability to see objectively. They might think they’ve taken a project or their talent as far as it can go, and, strictly speaking, given an individual’s limitations and inexperience, this may be true. But ultimately, to take a project where it needs to go, you’ll need to rely on an editor to help you get there. This is the most counterintuitive part of any creative process — just when you think you’re “done,” you’ll often find you’re not even close to being finished.

With my manuscript for Perennial Seller, I first had Nils Parker — who is a sensationally talented (and professional) writer and editor — edit it. Then I had another writer by trade and business partner of mine, Jimmy Soni, edit the whole manuscript after Nils. Only then did the manuscript get sent to my editor at Portfolio, Niki Papadopoulos. I am not exactly sure how many times I submitted a draft of Perennial Seller to Niki, but it was so many that I even included a footnote about it in the book itself: “I am adding this footnote to mark what is my fifth submission of the manuscript for this book. How many passes and rounds of editing that constitutes is impossible to track, but it means I’ve heard the ‘not there yet’ response at least four times.”

To give you an idea of the scale of revisions, these screenshots illustrate the days I spent chugging away, editing and re-writing on this book. It’s more than a year.

Here are the first few hundred words of the introduction, marked up by me as I was editing one of the first copies of the book I printed out.

This early editing pass is filled with arrows to move paragraphs around, crossed out sections that won’t make the cut, notes to myself about where to expand on the point I’m making, and how to do so. Even though it is very early in this process I’ve still made some proofreading edits as well. Notice that it’s just a printed Word document at this point.

Despite this rather extensive edit, these initial intro pages aren’t finished.

As you can see from the next draft I printed for markup, there’s still many concept-level (I call them meta-notes) that need to be addressed.

“Need to stress this is about right mindset.”

The note to myself that I “need to stress this is about right mindset”, from an early printed draft, shows that although just because I’m editing doesn’t mean I’m totally done writing and can move on to what is often thought of as editing — grammar, punctuation, and the like. I must make sure that this important idea gets properly incorporated and emphasized in Part I.

Making Perennial, perennial

One of the unique challenges this book presented to my editor and I was how to address trying to make Perennial Seller a perennial seller, and how to go about writing about it in the book. My editor thought that it was “too self-referential to be in the book itself,” and while I agree in some ways, it did feel as though it was necessary to address it.

The note from my editor: “Imagine this book being read in 2040, in Thai. What translates?” (the note is crossed out because I had addressed it) So as you can see, the perennial-ness of Perennial Seller was on the publisher’s mind throughout the process:

Communicating with the publisher

Here is the conversation from the “submission” of the Perennial Seller manuscript to my publisher. This means I officially sent it in and there are contractual implications for a manuscript “submission,” so this is a hugely important milestone for both parties. I can’t imagine any less fanfare:

From: Ryan Holiday Sent: Thursday, October 20, 2016 10:13 AM To: Niki Papadopoulos; Stephen Hanselman Subject: Perennial Submission Here you go! Ryan From: Niki Papadopoulos Date: Thu, Oct 20, 2016 at 10:15 AM Subject: RE: Perennial Submission To: Ryan Holiday, Stephen Hanselman Awesome! Start the next one. :)

A little over a week later, Niki got back to me with some encouragement as well as some homework:

From: Niki Papadopoulos Date: Fri, Oct 28, 2016 at 2:46 PM Subject: PERENNIAL edits back to you To: Ryan Holiday Cc: Stephen Hanselman, Leah Trouwborst I liked the new additions on art and genre. In the attached I mostly worked on smoothing the introduction, and I queried a few concepts that weren’t clear. In particular, the terms “marketing” and “platform” need more robust definitions — whether your own or someone else’s. But telling us about a thing isn’t the same as defining it. After this comes back to me, I’m going to ask you to do two things with that version: 1. Read aloud a printed version that I send to you and make comments/changes in the margins. Old school. 2. Highlight all of the examples that are about book publishing, and decide if you are happy with this balance. Believe it or not, I am not asking you to do these things in order to torture you. I want to encourage you to challenge yourself as a writer and to engage on a deeper level with your work. We have until early next year to transmit the manuscript to copyediting, so take your time. Niki

Prior to “submitting” the manuscript, I had sent Niki a few drafts of it. The first draft shared with my publisher was 39,000 words, which I sent in on Oct 30, 2015. A couple months later, on January 25, 2016 I sent a much improved version of the manuscript to my editor with the click of an email. Throughout this whole process I’d actually been working on my next book, The Daily Stoic, which was set to be published approximately 9 months from the date of this email about Perennial Seller:

From: Ryan Holiday Date: Mon, Jan 25, 2016 at 9:40 AM Subject: Perennial Seller (draft) To: Niki Papadopoulos, Stephen Hanselman Ok here it is. Niki, I wanted to get this off my plate and into the editing process so I can focus exclusively on Daily Stoic. It’s the only way that makes sense to me with the release dates, because as soon as DS is done I’ll need to be thinking mostly about the marketing for Ego and for DS. Excited to hear what you all think

A look at a section of the book across several drafts

Let’s take a look at how one section in the book evolved across several drafts.

In the earliest stages, ideas like the one below were simply written down on the aforementioned notecards:

Here’s what an early draft looked like after I’d written it up and taken a pass at editing it:

A page from the same section in a a subsequent early draft…

And yet another draft of the same section, with even more edits:

After countless rounds of feedback you’re still finding things to cut or change. Eventually it gets designed. Excerpts from the “Free. Free. Free.” section once more, this time designed and laid out how it would look as a page in the book. Notice that the example of 50 Cent has moved to the lead paragraph for this section. In the original draft I showed you earlier it was the very last paragraph, almost an afterthought.

At this point I am well on my way to having a finished manuscript, but I realized one of my notecards with the example of Soulja Boy which was perfect for this section had not made it into the book yet.

So I made sure to add that in the margin the next time I edited the book to ensure that it would make it into the book at the eleventh hour.

The “Free. Free. Free.” section has gotten tighter and tighter across the editing process, thus now most of the edits are pretty light. But elsewhere in this draft, extensive edits are still happening even this late in the game:

Word choice can also change a lot in the course of editing a manuscript. In this example, I initially described what John McPhee said as “dire.” Later, I decided that word choice was too over-the-top and changed it to “hyperbolically.”

In one of last edits I did for the book I changed the description of the McPhee quote again, this time to “dramatically.”

“Dramatically,” is how it now appears in commercial copies.

Often, writer and editor will disagree, as we see on this page:

In one comment, my editor with Portfolio asks me to cut an example from the book that demonstrated the importance of giving away content for free. The issue was that the story I was telling might ruffle a few feathers at his imprint at Penguin. Not wanting to cause any trouble, I tweaked it slightly to be more diplomatic. I won’t show the examples here but there are some not so nice responses I have scribbled in the margins from time to time as well over frustrating notes.

Copy Editing

If editing as a whole is the most grueling process of a book’s creation, then copy editing is the least pleasant phase of that process. Copy editing often feels like being audited — every question feels judgemental and no one likes being subjected to scrutiny. There’s an element of: ‘Who are you to tell me these things’ to it as well. Below is one of my least favorite exchanges in this round of copyediting where a whole sentence (an important one) was deleted without permission and I almost missed it.

Copy editing is not without merits though. It is where grammar and punctuation get fixed as well as accuracy and consistency. Basically, this is what most people think of when they think of editing, and it is not fun. Copy edits are often pedantic — the style guide says that Internet should be capitalized even though few normal humans do so. Or they involve a copy editor making changes that mess with the style and tone of the book. Copy editors do serve as an additional round of fact checking so the process is valuable.

Galleys

The above images are from the title page of the very first galley copies which are printed after copy editing. A book galley is essentially an advanced, uncorrected copy for limited distribution only. Sometimes galleys are basically the finished book but I tend to keep editing through them. This particular galley was the one that Tim Ferriss read while he was staying at my house in Austin — only Tim had time to read the Introduction and Part 1 while he was in town, so he ripped out those pages for me to use and took the rest of the galley with him to read later. The bindings on galleys are cheap, especially on the early galley copies, so this was easy to do. Notice the massive tear through its pages.

Tim tends to be a ruthless editor and most of his edits are suggestions to cut. Several large passages that were in the galley are not in the finished book. Why? Because he rightly pointed out how unnecessary they were.

And then even as late as the second pass — the final pass before the book goes to print — I was still tweaking and editing.

Here, I’ve cut out a quote, taped it to a notecard, and taped that into the pages of the manuscript I was editing as a reminder to myself to ask my editor if she thought it made sense to place it here. This was to be the very last edit before the book went to print.

Oh and sometimes you just have to take a 2 minute break to doodle on a draft:

Part V: PUBLISHING

Title, Subtitle, Cover Design

Nobody just hands you the perfect title, subtitle, cover, and artwork. Anyone can pick a cover for a book or throw together a safe title, but who can know the best choice for either of those decisions? Only the author.

On his books, Tim Ferriss spends hundreds of hours rigorously testing everything from his title to his cover ideas to his chapter titles. This process produced the title for his first book — the runaway mega-bestseller The 4-Hour Workweek — and set him up with perfect branding for an entire franchise (The 4-Hour Body, The 4- Hour Chef). You get a sense of what generates a response and what doesn’t by creating multiple cover options and bringing in a sample of friends with good taste and expertise to vote on them (tools like SurveyMonkey and Google Docs make this quite easy). Another client, Neil Strauss, spent nearly a year agonizing over whether to title one of his books Game Over or The Truth — both titles had advantages and disadvantages, and he knew it would take time and brainpower to gure out which was best. I remember shouting in exasperation at one point, “Neil, just choose!” But he’s the multimillion-bestselling author for a reason.

Most of the time, however, the opposite is true. I see creators who have had their design work done on Fiverr.com (for five dollars) or had a friend (or some person they knew) make their website for a few dollars. I cringe when I see these projects. It’s clear the creators have taken a shortcut or settled. “Why’d you choose that name?” “My daughter liked it.” “How do you like your cover?” “It’s good enough.” “The design of this feature is confusing.” “I know, but we’ll fix it later.” Obviously, these are choices anyone is free to make, but they are more in line with a side project than a career-defining would-be perennial seller. It’s certainly not how professionals would treat their work.

In the case of Perennial Seller, I weighed all of my options for title, subtitle, and design against each other, talked to people whose opinions I respect, and made decisions on what I believe are the strongest possible options for the book.

Here’s are two early title pages for Perennial Seller, which were just the first pages of the Word document. As you can see, the early subtitle was, “How To Make and Market A Classic,” which ended up not standing the test of time.

A later version of the title page is shown here, still using Word, and all of the markup and comments have been printed with the text so that the person who is editing by hand can see all of the changes. I got this draft back with a paper clipped note attached, “Excited to finalize this cover soon…” We were already much closer to the finished product as we had decided on the subtitle that would ultimately end up on the cover: The Art of Making and Marketing Work That Lasts. With the subtitle, I chose that because “The Art” implies a prescriptive element and “Lasts” is a little more flexible of a term than “Stands the Test of Time” (which was another option we played with).

Later on, my publisher and I had to go through several design concepts for the actual cover of the finished book. Here are a few early concepts we played with that made the book look old and used symbols that played on the themes in the book. Notice that all these concepts still have “The” in the title, which we later got rid of. Why did I ditch “The” in the title? After talking to my business partners at Brass Check, we decided that calling the book “The Perennial Seller” made it sound like it was referencing the book itself (i.e. book was THE perennial seller) and not the concept of perennial sellers in general.

Even though “Perennial Seller” seemed to be the strongest option and there were compelling reasons for choosing that, in January of this year I was having second thoughts. To test a few other options and hopefully assuage some of my concerns I asked a few people whose opinions I trust to weigh in via an online survey, which offered up dozens of title and subtitle options including “The Perennial Problem” and “The Perennial Ache.” Ultimately, “Perennial Seller” won out.

Prior to the next round of concepts, my editor and I discussed what our inspirations were for the Perennial cover. She kept coming back to Little Red Book of Selling. I found myself drawn to Satan Is Real and Unlabel by Marc Ecko, both of which were designed to look very old or like library books. My thinking was that doing something unique and retro with the cover would help sell our idea of “something that lasts” and create a talking point. I also was heavily inspired by F. Scott Fitzgerald’s All the Sad Young Men book cover, pictured above.

The combination of those cover inspirations are these red colored concepts.

And the final result with the final title, subtitle and all of the design and font. The three covers side by side by side for comparison:

The cover is such a gut feel. You know it when you see it. But I knew the book should:

Have a unique or unusual design to signal that it’s not like other books It should look weathered and old to symbolize that it has itself stood the test of time It should be subdued and classic.

Finishing the cover design is a satisfying piece of the creative process, but in keeping with one of the motifs in the book, this process seemingly does not end. I still needed to make decisions about the inside flaps of the book jacket. The publisher initially suggested flat black interior flaps and while I was okay with the color change, I was not okay abandoning the old book theme. I wanted to make sure there was some transition from old look to new.

Legal review

One of the last hurdles that all traditionally published books encounter is legal review. The publisher works with an in-house lawyer to make sure nothing in the book is, well, illegal. In the case of Perennial Seller, there were only a handful of very minor concerns, which we addressed.

From: Niki Papadopoulos Date: Thu, Nov 17, 2016 at 2:39 PM Subject: PERENNIAL fair use queries from legal To: Ryan Holiday Cc: Stephen Hanselman, Leah Trouwborst I shared select parts of this manuscript with Linda Cowen, our in-house counsel, to see if she thought particular song lyrics constituted fair use or would require permission. Most of them were fine, except for the attached three queries. If you let me know what you’d like to do in each case, we can make the change to the manuscript internally. Niki

Audiobook

Even when it comes time to do the audiobook, I am still making changes. I read my own books for the audiobooks, and I make sure to note down pronunciations, names, etc. so as not to waste time the in studio (since it takes so long anyway). Here, you can see I’ve decided to change the word choice from “flipping” to “scrolling.” The finished book will be updated and corrected with all of the things I catch when I read the audiobook so that the physical book and the audiobook match almost perfectly.

Here’s an email I sent to Niki with a few of the mistakes I noted down:

From: Ryan Holiday Date: Sun, Jun 4, 2017 at 11:58 PM Subject: Manuscript/Audiobook mistakes PS To: Niki Papadopoulos, Vivian Roberson Hi Niki & Vivian, Caught a few things reading the audiobook for Perennial that we should change for whatever printing comes next, as well as for ebook before release. pg 39 “The answer, of course, is that was created by the process.” Change to “The answer, of course, is that it was not created by them, it was created by the process.” pg 76. Footnote. Should say “used THE ‘car test” pg 100 “Nothing has sunk more creators…” Sentence has a THAT in it that shouldn’t be there pg 130 “when I was flipping through my music library” flipping should become “scrolling.” pg 143/145 Web is capitalized so is Internet (as well as on several other pages). But I know I caught this in copy-editing and earlier rounds. I don’t capitalize those words and feel it makes me look quite stupid to do so. Please revert how I intended in any instances. pg 166 change two hundred thousand to four hundred thousand pg 168 change sentence to “We offered a free T-shirt to any student on campus — to be picked up at their LGBTQ center.” pg 169 Delete “And that’s a useful way to think about….” replace with “And that’s a useful standard for good advertising: is it about your ego or is about doing something of value?” The existing sentence does not make much sense pg 179 “to bear on” becomes “to bring to bear on” pg 189 “that one day I might recommend” not “recommended” pg 198 “found a of a prestos book PR firm” not firms pg 215 change to “working for bigger and more famous musicians and while designing materials for big music…” delete as well as pg 215 “Which charts are” should just be “Charts are” Thank you R

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And then one day copies of your own book arrive. You remember when it was just an idea. You remember the times you thought about quitting, but now it exists. It’s one of the coolest feelings ever. And, of course, you still find errors. There will be things on the cover that you need to tweak (*cough* errors introduced by your publisher) and you’ll catch them and be distracted by them.

But really there won’t be time for that because then the marketing begins. And then by the time that ends, the next race will begin. A lot of people sit down to write a book. Many don’t make it past that point. Plenty get something finished, but are intimidated by the maze that is publishing, promoting, selling. Of the relative few that make it through there, only some have the stamina to start the next one. As Craig Newmark told me when I interviewed him for Perennial, and asked him what it was like to create something like Craiglist which has become such an institution, he said “It feels nice for a moment, then surreal, then back to work.”

The same goes for books.

See you next time.