This was David Ogilvy's rule: “Never use jargon words like reconceptualize, demassification, attitudinally, judgmentally. They are hallmarks of a pretentious ass.” The other one is: “Never use two words where one will do.” Write like you talk.

[20] Cut out the jargon

Hemingway advised fellow writer Thomas Wolfe “to break off work when you ‘are going good.’—Then you can rest easily and on the next day easily resume.” Brian Koppelman has referred to this as stopping on “wet edge.” It staves off the despair the next day and brings a fresh perspective to your writing.

[18] Stop on the “wet edge”

The bulk of the work is researching — collecting stories, anecdotes, and data to marshal your argument. The writing is stringing those pieces together. Ryan has used stuff he has found in in-flight magazines, discovered snippets on social media, even heard things mentioned on TV. As Shelby Foote <a href="http://www.theparisreview.org/interviews/931/the-art-of-fiction-no-158-shelby-foote">put it in an interview </a>with The Paris Review : “I can’t begin to tell you the things I discovered while I was looking for something else.”

[2] Always be researching

When Thomas Mann described a writer as “someone to whom writing does not come easy,” he was putting it lightly. Walker Percy said “that writing is like suffering from a terrible disease for a certain period of time. Then when you finish you get well again.” Challenges help you improve and grow. Embrace them.

[22] It’s OK that it’s hard

Ryan Holiday has found that picking one song—usually something he is not proud to listen to—and listening to it on repeat, over and over and over again is the best way to get into a rhythm and flow. It not only shuts out outside noise but also parts of the conscious mind you don’t need to hear from while you are writing.

[11] Listen to the same song on repeat

Great artists work. Mediocre artists talk a lot about tools. Software does not make you a better writer. If classics were created with quill and ink, you’ll probably be fine with a Word Document. Don't let technology distract you from your goal — to write. Helen Simpson has “Faire et se taire” from Flaubert on a Post-it near her desk, which she translates as “Shut up and get on with it.”

[13] Don’t let the tools distract you 

Ryan Holiday's editor Niki Papadopoulos once told him, “It’s not what a book is. It’s what a book does .” This is why musicians follow the “car test” (how does the song sound in a car driving down the highway). It’s just about whether you like it…but about what it does for the people buying it.

[19] Make something that does a job

You need what the strategist and theorist <a href="https://www.thepaintedporch.com/products/war4?_pos=1&_sid=2cfb11897&_ss=r">John Boyd </a>called the “draw-down period.” Take a break right before you start. To think, to reflect, to let things settle. Articulate your thoughts and start with a clear mind.

[10] Embrace draw-down periods

“To have something to say,” Schopenhauer said, “by itself is virtually a sufficient condition for good style.” Share your ideas instead of worrying about the outcome of expression.

[6] Have something to say

Thucydides had Herodotus. Gibbon had Thucydides. Shelby Foote had Gibbon. Every playwright since Shakespeare has had Shakespeare. Everyone has a master to learn from. Be it Elon Musk or Adam Grant, let someone inspire and teach you.

[7] Have a model in mind

Success requires greater investment in the creative process. Pay for professional help that aids your creative process. There’s a saying: If you think pros are expensive, try hiring an amateur.

[5] Work with great people 

Each morning, Ryan<a href="https://ryanholiday.net/the-most-important-thing-you-can-do-each-morning/"> journals in three small notebooks</a>. The whole ritual takes 15 minutes and by the time he is finished, he is centered, calm and most importantly, primed to do the actual writing. Journaling also helps you stay mindful.

[16] Journal every morning

Don’t talk about projects until you’re finished. Save that carrot for the end. Talking and doing fight for the same resources. Staying mum about your progress until you reach a milestone also prevents embarrassment if you unexpectedly quit.

[17] Don’t talk about the book (as much as you can help it)

Many a times, Ryan has thought of a great line or solved an intractable writing problem while running or swimming. Exercise is also an easy win every day. Writing can go poorly, but going on a run always goes well.

[14] Get some strenuous exercise every day

James Altucher has a great rule that you can steal: Write what you’re afraid to say. If your stuff isn’t scaring you, you’re not pushing yourself enough. Writing things down also creates a channel for you to express yourself.

[15] Write about the things you’re afraid to talk about.

When you get stuck, talk the ideas through with someone you trust. As Seth Godin observed, “no one ever gets talker’s block.” Sharing ideas with others also helps us refine them.

[21] Talk it out

As <a href="https://geni.us/fAD1O">Vivian Gornick </a>explains, “What happened to the writer is not what matters; what matters is the large sense that the writer is able to make of what happened.”

[23] Remember…it’s all material 

The best way to start writing a book is to produce “two crappy pages a day.” It’s by carving out a small win each and every day — getting words on the page — that <a href="https://medium.com/the-mission/here-with-2-years-of-exhausting-photographic-detail-is-how-to-write-a-book-fda1a6b40802">a book is created </a>. Hemingway once said that “the first draft of anything is shit,” and he’s right.

[12] Make little progress each day

A book is made of books. “The greatest part of a writer’s time is spent in reading; a man will turn over half a library to make one book,” Samuel Johnson said. As Ryan Holiday was putting together the bibliography for <a href="https://store.dailystoic.com/pages/courage">Courage </a>, he counted something like 300 books he was directly sourcing from.

[1] Read. Read. Read.

Ryan Holiday turned in a book proposal for his next book before the latest one came out. "When I have a commitment that I know I have to meet, resistance doesn’t have the time or space to creep in. Right now I am on a book year path for the next four years. It keeps me honest and keeps me working. Meet deadline, or death."

[4] Make commitments

<a href="https://www.thepaintedporch.com/products/confederacy-of-dunces-anniversary?_pos=1&_sid=cdbc4ba8b&_ss=r">A Confederacy of Dunces </a>was rejected by publishers. After the author’s suicide, it won the Pulitzer prize. People don’t know shit. YOU know. So love it while you’re doing it. Success can only be extra. You can't control everything. What you can, however, is your work. Focus on that.

[9] Focus on What You Control

Print and put a couple of <a href="https://ryanholiday.net/print-out-good-advice-and-put-it-where-you-work-you-wont-be-able-to-run-away-from-it/">important quotes up on the wall </a>to help guide you (either generally, or for a specific project). Ryan had a quote from Machiavelli on the wall to inspire the style and ethos of a book he was working on.

[3] Put good advice where you work

You don’t “find the book as you write.” You have to do the hard work of solving the problem first. You have to figure out the best route, too. Before you start to write, articulate the idea in one sentence, one paragraph and one page. Nassim Taleb wrote in <a href="https://www.thepaintedporch.com/products/selfhelp3?_pos=1&_sid=e9558a5cb&_ss=r">Antifragile </a>that every sentence in the book was a “derivation, an application or an interpretation of the short maxim” he opened with.

[8] Know where you’re going

Similar ideas to [8] Know where you’re going

Writing a book: Getting started