Writing looks fun, but doing it professionally is hard. Like really hard. “Why on earth am I doing this?”-hard.

Which is probably why so many people want to write, yet so few actually do. But there are ways to make it easier, as many writers can tell you. Tricks that have been discovered over the centuries to help with this difficult craft.

In another industry, these tricks would be considered trade secrets. But writers are generous and they love to share (often in books about writing). They explain their own strategies for how to deal with writer’s block to how to make sure your computer never eats your manuscript. They give away this hard-won knowledge so that other aspiring writers won’t have to struggle in the same way. Over my career, I’ve tried to collect these little bits of wisdom in my commonplace book (also a writer’s trick which I picked up from Montaigne) and am grateful for the guidance they’ve provided.

Below, I’ve shared a collection of writing hacks from some amazing writers like Kurt Vonnegut, George Orwell, Stephen King, Elizabeth Gilbert, Anne Lamott, and Raymond Chandler. I hope it’s not too presumptuous but I snuck in a few of my own too (not that I think I’m anywhere near as good as them).

Anyway, here’s to making this tough job a tiny bit easier!

[*] When you have an idea for an article or a book—write it down. Don’t let it float around in your head. That’s a recipe for losing it. As Beethoven is reported to have said, “If I don’t write it down immediately I forget it right away. If I put it into a sketchbook I never forget it, and I never have to look it up again.”

[*] The important thing is to start. At the end of John Fante’s book Dreams from Bunker Hill, the character, a writer, reminds himself that if he can write one great line, he can write two and if he can write two he can write three, and if he can write three, he can write forever. He pauses. Even that seemed insurmountable. So he types out four lines from one of his favorite poems. What the hell, he says, a man has to start someplace.

[*] In fact, a lot of writers use that last technique. In Tobias Wolff’s autobiographical novel Old School, the character types the passages from his favorite books just to know what it feels like to have those words flow through his fingertips. Hunter S. Thompson often did the same thing. This is another reason why technologies like ebooks and Evernote are inferior to physical interaction. Just highlighting something and saving it to a computer? There’s no tactile memory there.

[*] “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

[*] Tim Ferriss has said that the goal for a productive writing life is “two crappy pages a day.” Just enough to make progress, not too ambitious to be intimidating.

[*] They say breakfast (protein) in the morning helps brain function. But in my experience, that’s a trade-off with waking up and getting started right away. Apparently Kurt Vonnegut only ate after he worked for 2 ½ hours. Maybe he felt like after that he’d earned food.

[*] Michael Malice has advised “don’t edit while you write.” I think this is good advice.

[*] In addition to making a distinction between editing and writing, Robert Greene advises to make an equally important distinction between research and writing. Trying to “find where you’re going” while you’re doing it is begging to get horribly lost. Writing is easier when the research is done and the framework has been laid out.

[*] Nassim Taleb wrote in Antifragile that every sentence in the book was a “derivation, an application or an interpretation of the short maxim” he opened with. THAT is why you want to get your thesis down and perfect. It makes the whole book/essay easier.

[*] Break big projects down into small, discrete chunks. As I am writing a book, I create a separate document for each chapter, as I am writing them. It’s only later when I have gotten to the end that these chapters are combined into a single file. Why? The same reason it feels easier to swim seven sets of ten laps, than to swim a mile. Breaking it up into pieces makes it seem more achievable. The other benefit in writing? It creates a sense that each piece must stand on its own.

[*] Embrace what the strategist and theorist John Boyd called the “draw-down period.” Take a break right before you start. To think, to reflect, to doubt.

[*] On being a writer: “All the days of his life he should be reading as faithfully as his partaking of food; reading, watching, listening.” John Fante

[*] Don’t get caught up with pesky details. When I am writing a draft, I try not to be concerned with exact dates, facts or figures. If I remember that a study conducted by INSERT UNIVERSITY found that XX% of businesses fail in the first FIVE/SIX? months, that’s what I write (exactly like that). If I am writing that on June XX, 19XX Ronald Reagan gave his famous “Tear Down This Wall” speech in Berlin in front of XX,XXX people, that’s how it’s going to look. Momentum is the most important thing in writing, so I’ll fill the details in later. I just need to get the sentences down first. “Get through a draft as quickly as possible,” is how Joshua Wolf Shenk put it.

[*] Raymond Chandler had a trick of using small pieces of paper so he would never be afraid to start over. Also with only 12-15 lines per page, it forced economy of thought and action—which is why his stuff is so readable.

[*] In The Artist’s Way, Julia Cameron reminds us that our morning pages and our journaling don’t count as writing. Just as walking doesn’t count as exercise, this is just priming the pump—it’s a meditative experience. Make sure you treat it as such.

[*] Steven Pressfield said that he used to save each one of his manuscripts on a disk that he’d keep in the glovebox of his car. Robert Greene told me he sometimes puts a copy of his manuscript in the trunk of his car just in case. I bought a fireproof gun safe and keep my stuff in there—just in case.

[*] My editor Niki Papadopoulos at Penguin: “It’s not what a book is. It’s what a book does.”

[*] While you are writing, read things totally unrelated to what you’re writing. You’ll be amazed at the totally unexpected connections you’ll make or strange things you’ll discover. As Shelby Foote put it in an interview with The Paris Review: “I can’t begin to tell you the things I discovered while I was looking for something else.”

[*] Writing requires what Cal Newport calls “deep work”—periods of long, uninterrupted focus and creativity. If you don’t give yourself enough of this time, your work suffers. He recommends recording your deep work time each day—so you actually know if you’re budgeting properly.

[*] Software does not make you a better writer. Fuck Evernote. Fuck Scrivner. You don’t need to get fancy. If classics were created with quill and ink, you’ll probably be fine with a Word Document. Or a blank piece of paper. Don’t let technology distract you. As Joyce Carol Oates put it in an interview, “Every writer has written “by hand” until relatively recent times. Writing is a consequence of thinking, planning, dreaming — this is the process that results in “writing,” rather than the way in which the writing is recorded.”

[*] Talk about the ideas in the work everywhere. Talk about the work itself nowhere. Don’t be the person who tweets “I’m working on my novel.” Be too busy writing for that. 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.”

[*] Why can’t you talk about the work? It’s not because someone might steal it. It’s because the validation you get on social media has a perverse effect. You’ll less likely to put in the hard work to complete something that you’ve already been patted (or patted yourself) on the back for.

[*] When you find yourself stuck with writer’s block, pick up the phone and call someone smart and talk to them about whatever the specific area you’re stuck with is. Not that you’re stuck, but about the topic. By the time you put your phone down, you’ll have plenty to write. (As Seth Godin put it, nobody gets “talker’s block.”)

[*] Keep a commonplace book with anecdotes, stories and quotes you can always use—from inspiration to directly using in your writing. And these can be anything. H.L. Mencken for example, would “methodically fill a notebook with incidents, recording scraps of dialogue and slang, columns from the New York Sun.”

[*] As you write down quotes and observations in your commonplace book, make sure to do it by hand. As Raymond Chandler wrote, “when you have to use your energy to put words down, you are more apt to make them count.”

[*] Elizabeth Gilbert has a good trick for cutting: As you go along, ‘Ask yourself if this sentence, paragraph, or chapter truly furthers the narrative. If not, chuck it.’ And as Stephen King famously put it, “kill your darlings, kill your darlings, even when it breaks your egocentric little scribbler’s heart, kill your darlings.”

[*] Strenuous exercise everyday. For me, and for a lot of other writers, it’s running. Novelist Don DeLillo told The Paris Review how after writing for four hours, he goes running to “shake off one world and enter another.” Joyce Carol Oates, in her ode to running, said that “the twin activities of running and writing keep the writer reasonably sane and with the hope, however illusory and temporary, of control.”

[*] Ask yourself these four questions from George Orwell: “What am I trying to say? What words will express it? What image or idiom will make it clearer? Is this image fresh enough to have an effect?” Then finish with these final two questions: “Could I put it more shortly? Have I said anything that is avoidably ugly?”

[*] As a writer you need to make use of everything that happens around you and use it as material. Make use of Seinfeld’s question: “I’m never not working on material. Every second of my existence, I am thinking, ‘Can I do something with that?’”

[*] Airplanes with no wifi are a great place to write and even better for editing. Because there is nowhere to go and nothing else to do.

[*] Print and put a couple of important quotes up on the wall to help guide you (either generally, or for a specific project). Here’s a quote from a scholar describing why Cicero’s speeches were so effective which I put on my wall while I was writing my first book. “At his best [Cicero] offered a sustained interest, a constant variety, a consummate blend of humour and pathos, of narrative and argument, of description and declamation; while every part is subordinated to the purpose of the whole, and combines, despite its intricacy of detail, to form a dramatic and coherent unit.” (emphasis mine)

[*] Focus on what you’re saying, worry less about how. As William March wrote in The Bad Seed, ”A great novelist with something to say has no concern with style or oddity of presentation.”

[*] A little trick I came up with. After every day of work, I save my manuscript as a new file (for example: EgoIsTheEnemy2-26.docx) which is saved on my computer and in Dropbox (before Dropbox, I just emailed it to myself). This way I keep a running record of the evolution of book. It comforts me that I can always go back if I mess something up or if I have to turn back around.

[*] Famous ad-man David Ogilvy put it bluntly: “Use short words, short sentences and short paragraphs.”

[*] Envision who you are writing this for. Like really picture them. Don’t go off in a cave and do this solely for yourself. As Kurt Vonnegut put it in his interview with The Paris Review: “…every successful creative person creates with an audience of one in mind. That’s the secret of artistic unity. Anybody can achieve it, if he or she will make something with only one person in mind.”

[*] Do not chase exotic locations “to do some writing.” Budd Schulberg’s novel The Disenchanted about his time with F. Scott Fitzgerald expresses the dangers well: “It was a time everyone was pressing wonderful houses on us. ‘I have a perfectly marvelous house for you to write in,’ they’d say. Of course no one needs marvelous houses to write in. I still knew that much. All you needed was one room. But somehow the next house always beckoned.”

[*] True enough, though John Fante said that when you get stuck writing, hit the road.

[*] Commitments (at the micro-level) are important too. An article a week? An article a month? A book a year? A script every six weeks? Pick something, but commit to it—publicly or contractually. “Quantity produces quality,” as Ray Bradbury put it.

[*] “Don’t ever write anything you don’t like yourself and if you do like it, don’t take anyone’s advice about changing it. They just don’t know.” –Raymond Chandler

[*] Neil Strauss gave me another helpful iteration of that idea (which I later learned is from Neil Gaiman): “When someone tells you something is wrong with your writing, they’re usually right. When they tell you how to fix it, they’re almost always wrong.”

[*] Ogilvy had another good rule: “Never use jargon words like reconceptualize, demassification, attitudinally, judgmentally. They are hallmarks of a pretentious ass.”

[*] Print out the work and edit it by hand as often as possible. It gives you the reader’s point of view.

[*] 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 (Rounders, Billions) has referred to this as stopping on “wet edge.” It staves off the despair the next day.

[*] Keep the momentum: “Never stop when you are stuck. You may not be able to solve the problem, but turn aside and write something else. Do not stop altogether.” Jeanette Winterson

***

That taps me out for now. But every time I read I compile a few more notecards. I’ll update you when I’ve got another round to share.

In the meantime, stop reading stuff on the internet and get back to writing!

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