The 50 Best Things I’ve Ever Learned Or Taught Myself About Writing

The new year is almost upon us, and with that comes the inevitable resolution. Whether or not this new “you” includes a more creative or eloquent self, becoming a better writer is an invaluable skill.

So as a Christmas (or “holiday” if that works better) gift, I wanted to post the 50 most important things I’ve learned about writing; tidbits from people much better at it than me, and my own dispatches from lobbing countless salvos at the impervious blinking cursor.

Happy Holidays and a Happy Early New Year to all of you. May your resolutions find footing in the swirling tides of our lives.

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First, let’s baptize ourselves in the exfoliating water, of Steven Pressfield (from: Nobody Wants To Read Your Shit)

In the real world, no one is waiting to read what you’ve written.

Sight unseen, they hate what you’ve written. Why? Because they might have to actually read it. Nobody wants to read anything. Let me repeat that. Nobody—not even your dog or your mother—has the slightest interest in your commercial for Rice Krispies or Delco batteries or Preparation H. Nor does anybody care about your one-act play, your Facebook page or your new sesame chicken joint at Canal and Tchoupitoulas.

When you understand that nobody wants to read your shit, you develop empathy.

A good concept makes the audience see your product from a very specific, sympathetic point of view and by its logic (or faux logic) renders all other points of view and all competing products moot and impotent.

Now that that lozenge is precariously lodged in the back of our throat, let’s try to wash it down.

ON WHAT YOU SHOULD WRITE

1. “The #1 question that writers ask themselves: “I’ve got a million ideas. How do I know which one to work on?” Answer: Write your White Whale. Which idea, of all those swimming inside your brain, are you compelled to pursue the way Ahab was driven to hunt Moby Dick? Here’s how you know—you’re scared to death of it. It’s good to be scared. You should be scared. Mediocre ideas never elevate the heart rate. Great ones make you break out in a sweat.” - Steven Pressfield

ON MINDSET

2. "Being a writer can feel a lot like writing and giving up on writing at the same time. What seems to separate those who write from those who don’t is being able to stand it." - Alexander Chee, from his book, How To Write An Autobiographical Novel

3. "Writing is an act of ego, and you might as well admit it. Use its energy to keep yourself going. You are writing primarily to please yourself, and if you go about it with enjoyment you will also entertain the readers who are worth writing for. Believe in your own identity and your own opinions...Writing is such lonely work that I try to keep myself cheered up." - William Zinsser, On Writing Well

4. “When Kurt Vonnegut wrote, ‘Write to please just one person,’ what he was really saying was write for yourself. Don’t try to please anyone but yourself. . . . The second you start doing it for an audience, you’ve lost the long game because creating something that is rewarding and sustainable over the long run requires, most of all, keeping yourself excited about it. . . . Trying to predict what [an audience will] be interested in and kind of pretzeling yourself to fit those expectations, you soon begin to begrudge it and become embittered—and it begins to show in the work. It always, always shows in the work when you resent it. And there’s really nothing less pleasurable to read than embittered writing.” - Maria Popova, creator of Brain Pickings (from an interview in Tim Ferriss’ Tools of Titans)

You want to write so well that you inspire half your readers to continue writing, and you convince the other half to quit writing, because I’ve read certain books that the writing is almost too good. I’m a masochist though. Only 49% of me wants to quit. My ego always slings the deciding vote.

5. “If you’re a writer, particularly if you’re a writer or a storyteller of any kind, there is something already kind of monstrously wrong with you. Let’s face it, it is an unreasonable attitude to look in the mirror in the morning and think, “You know, there are people out there who would really like to hear my story.” You know, “I’m an interesting guy, and I have interesting things to say.” Look, the numbers overwhelmingly disprove that notion. It’s an insane notion. Most writers fail. So the kind of drive — the kind of compulsion to spend a year or two of your life writing a book in the hope that people will buy it, that’s what’s called narcissism. - Anthony Bourdain from an interview in Men’s Journal.

ON MINDSET

6. The fear of writing isn’t so much about the act of writing, it’s the notion that if you do the thing you say you want to do, one day you won’t be there to protect it. That’s our fear. The thing I get scared of, is not that I’m not good enough, and not that I don’t have anything to say, it’s that when I release my baby into the world, I am not there to defend it. You don’t get to sit behind someone’s shoulder and answer their questions about your piece, article, post or book. Writing is a one way relationship. There is no Q&A. Trying to make something perfect keeps us from ever sharing it. And to write is to share, eventually. I once heard Seth Godin speak at an event. There was a Q&A at the end where a man asked Seth how he knows when the book he is writing is good enough since facts and history keep changing. Seth responded with, “What is it costing you to be perfect?” There is no right or wrong way, but I can say, death by research is no way to go. Eventually you have to write. Eventually you have to let go.

ON GETTING OUT OF OUR OWN WAY

7. Don’t delete, reappropriate.

Within a piece I’m working on, I use *** to start a new, tangential idea; and I use --- to move things in the “probably not going to make it” pile. I don’t have to fret about deleting my own words. We writers love all our words. By reappropriating I can make sure that all of them still exist somewhere, even if it’s at the bottom of a google doc that I’ll never open again.

The --- goes at the end (bottom) of my piece and the *** goes right before it so that my writing eventually looks like this:

Here is the current draft

***

Here’s what might be in it; or here’s some possible ideas I might keep

---

Here’s what's getting cut

8. At the beginning of an idea (a post, about page, an article, whatever) you have to give yourself permission to suck. When I’m tackling a new “whatever,” I set a timer for 30 minutes and I write. Only one rule in that half hour: I’m not allowed to delete. I try not to even reappropriate (rule #7 above). I get comfortable with the act of creating.

Lo and behold, there is a thought germinating under the mulch in the fourth paragraph that I’ve written. I would have never discovered it had I not gotten out of my own way. Let an editor edit (see: decimate) your stuff. You, you delicate flower, just need to write. In the first 30 minutes, everything stays, everything has a chance. In the early stages of a new piece, we need all the nutrients we can get.

9. “We do not write in order to be understood; we write in order to understand.” - Clive Thompson from his book, Smarter Than You Think

For me the writing process isn’t a manifestation of what I’ve discovered, it’s a discovery of what I’ll manifest. I write to get clear on how I view the world. We tell ourselves we’ll write when we figure it out, but we keep replaying the same two thoughts in our head over and over. Get to the fourth thought. That’s where things get interesting.

10. “I learned that the first three pages of a draft are usually where you clear your throat, that most times, the place your draft begins is around page four.” - Alexander Chee, from his book, How To Write An Autobiographical Novel

11. Never ever waste time researching a specific fact or number during a writing session. Batch research.

“Neil (Strauss) and I, and many other writers, use “TK” as a placeholder for things we need to research later (e.g., “He was TK years old at the time.”). This is common practice, as almost no English words have TK in them (except that pesky Atkins), making it easy to use Control-F when it’s time to batch-research or fact-check.” - Tim Ferriss - Tools of Titans

12. One of the best pieces of advice I’ve received for writing was a mantra: “Two crappy pages per day.” - Neil Strauss

ON EDITING

13. “The great thing about writing (as opposed to climbing Mt. Everest or raising children or going to war) is the work sits still. What we did yesterday stays intact on the page, where we can rethink it, revise it, rework it tomorrow.” - Steven Pressfield

14. Give yourself time to edit when you give yourself time to write. An editing session is your reward. You get to be a critic without feeling like you actually wrote anything. Your writing will feel like your writing after the edit, not after the writing.

Editing is as important of a process as writing. That’s why I always measure the time I’m working on something, not how many words I produced. Gardening is as much pruning as it is planting.

15. The sentence that you’re in love with is usually the thing that is keeping your piece from being coherent. I’ve noticed that my writing becomes more flowery when I either don’t believe in what I’m saying or I don’t know what I’m trying to say. Beware of the beauty and the clutter. Oftentimes they are things we hide behind when we don’t know what we stand for.

“Writing improves,” William Zinsser said, “in direct ratio to the number of things we can keep out of it that shouldn’t be there.”

16. Alexander Chee, on describing a particular writing class, “One afternoon, at her direction, we brought in paper, scissors, and tape, and several drafts of an essay, one that we struggled with over many versions. Now cut out only the best sentences, she said, and tape them on a blank page. And when you have that, write in around them, she said. Fill in what’s missing and make it reach for the best of what you’ve written thus far. I watched as the sentences that didn’t matter fell away. You might think that your voice as a writer would emerge naturally, all on its own, with no help whatsoever, but you’d be wrong. What I saw on the page was that the voice is in fact trapped, nervous, lazy. Even, and in my case most especially, amnesiac. And that it has to be cut free.”

17. Paddy Chayefsky, who’s won three Oscars for screenplay writing, famously said, “As soon as I figure out the theme of my play, I write it down on a thin strip of paper and Scotch-tape it to the front of my typewriter. After that, nothing goes into that play that isn’t on-theme.”

If I’m struggling with how to make something fit, it’s usually because I’m contradicting myself and I just don’t know it yet. As soon as possible, figure out what it is you’re trying to say. If my writing doesn’t make sense, I will go to the top of the piece and write down the points I think I’m trying to make before reviewing my work like a detective. Inevitably, I’ll find the sentence that has murdered my argument.

18. "Every sentence must do one of two things— reveal character or advance the action." - Kurt Vonnegut

19. “The Period. There’s not much to be said about the period except that most writers don’t reach it soon enough. If you find yourself hopelessly mired in a long sentence, it’s probably because you’re trying to make the sentence do more than it can reasonably do—perhaps express two dissimilar thoughts.” - William Zinsser

I can’t tell you how many times a “stuck” passage for me was fixed by looking at a long sentence. Usually, there, at the end of it, was a parasite feeding on the main argument. I didn’t notice the linguistic barnacle because it was camouflaged in pretty language.

20. “A clear sentence is no accident. Very few sentences come out right the first time, or even the third time. Remember this in moments of despair. If you find that writing is hard, it’s because it is hard.” - William Zinsser

The illusion of the talented writer sitting at a computer and mashing out a masterpiece in one go is a myth. Writing is like an archeological dig. It is an unearthing of words, not a transcription of them. There’s a strange feeling of being impressed by something I wrote and having no recollection of when I wrote it or how I came up with it. That’s because these words were sculpted by multiple artists in me, at different times; each one contributing something to the final piece; Frankenstein’s prose, if you will. Writing is part 3-D modeling and part sculpting. Both creative processes are happening at the same time. Adding the form, theme, style and plot from within, and from the outside, chiseling away lazy, excess, and contradictory writing until they meet somewhere in the middle to reveal your masterpiece.

21. “It is a rookie workshop mistake to go home and address everything your readers brought up directly, and if there is a problem inherent to workshop, it is that some people credulously do that. A reader experiencing what they called a pacing problem could be experiencing an information problem—lacking information that would make sense of the story for them about the character, the place, the situation—and problems with plot are almost always problems that begin in the choice of point of view. I learned to use a class’s comments as a way to sound the draft’s depths, and as a result had a much better experience of the workshop overall.” - Alexander Chee

ON FICTION WRITING

22. Again, I’m going to let Steven Pressfield do the heavy lifting. From Nobody Wants To Read Your Shit:

Writing a novel is not for the faint of heart. Consider what you’re letting yourself in for: a two- to three-year siege with no external validation or reinforcement, no paycheck, and no day-to-day structure except that which you impose yourself. Support from friends and family? Dubious. Future rewards? Iffy at best. And we’re not even talking about the work. Will your significant other understand?

The best advice for the mate of a novelist is to sit down, pour yourself a stiff brandy, and make sure in your heart that this is a starship you’re really ready to blast off in. No one, trust me, can write a novel and not become completely submerged in it. You have to or you can’t keep going. Think about how crazy that is. You, the writer, are having conversations all day (and all night) with personalities who don’t exist.

Those with whom you spend every working hour, and about whom you care most passionately possess no corporeal reality. You have entered a realm whose depths and dimensions are known to you alone. You can try to involve your spouse, yeah, but that glassy, semi-panicky look in his/her eyes is real. He/she has just realized that they’re linked for life with a person they do not know.

One of the weirdest things in the world is to look in the mirror (I mean really look) when you’re in the throes of writing a novel. You don’t even recognize yourself. You are dealing with the Muse now. You are on her turf. She owns you. You have ceded your psychic autonomy to forces based in a different dimension of reality. This is the Foreign Legion, baby, and I don’t mean France. It’s a rush. It’s the rush. But it also can scare the shit out of you. I’m not kidding when I say that your closest, and possibly only confidant has now become your cat, your dog, your goldfish. They don’t get you either, but at least they’re not the mother or father of your children. Why do so many novelists become drunks or addicts? Why do so many take the gas pipe? You’re playing with dynamite when you type CHAPTER ONE.

Writing a novel is like crossing the continent in a prairie schooner. You, the pioneer, must master the art of delayed gratification. You have to break the trek down in your mind into mini-treks whose distance and demands your sanity can handle. Can you do a first draft in three months? Too daunting? How about a rough sketch in three weeks? Still too scary? Maybe a rough-rough in seven days? Remember, the enemy in an endurance enterprise is not time. The enemy is Resistance.

I think that about sums it up.

ON NON - FICTION WRITING

This list was long, but leaving it to William Zinsser makes the most sense.

23. “Every successful piece of nonfiction should leave the reader with one provocative thought that he or she didn’t have before. Not two thoughts, or five—just one. So decide what single point you want to leave in the reader’s mind.”

24. “Grip the reader at the first sentence and end on a great sentence. They are the power to pull in at the beginning, and to uplift when letting go.”

25. “Surprise is the most refreshing element in nonfiction writing.”

26. “Most nonfiction writers have a definitiveness complex. They feel that they are under some obligation—to the subject, to their honor, to the gods of writing—to make their article the last word. It’s a commendable impulse, but there is no last word.”

ON SELLING

For me, no one beats Ash Ambirge when it comes to writing persuasive shit to convince people to buy from you. Here are some of her best bits through the years:

27. Can’t figure out who you’re selling to? Ask yourself these three questions:

• What do they do on Sunday mornings?

• What do they do on Monday mornings?

• Why?

28. Rules of Selling

• People Love To Buy

• People Will Always Look For A Reason Why They Don’t Need Something

• People Are Naturally Suspicious

• People Want To Feel Better About Themselves

29. You don’t sell features. You don’t sell benefits of those features. You sell psychological benefits to someone’s pain.

Don’t sell the feature (24/7 security) or the benefit (someone is always there when you need it). Sell the psychological benefit (you will be able to sleep at night).

It’s not “weekly calls and accountability groups.” It’s not even “Become a better writer,” it’s “finish the first draft of your novel in a month.”

30. People don’t buy products, they buy better versions of themselves

31. Great writing is about one thing only—engaging the reader emotionally. You’re the only person responsible for the reader’s emotional response. Your job is not to write. Your job is to connect through words. We all know the difference between motel and boutique hotel.

32. What the words remind you of is more important than what they mean.

33. You mix desire and tension to get attention.

Yeah, all that is Ash Ambirge.

If you want to see the best product descriptions online, go look at any one of them at J. Peterman.

ON WRITING BETTER

34. “Clichés are the enemy of taste.” - William Zinsser

Here are some you should put in a catacomb:

• Reckless abandon

• Heart and soul

• Eternal optimist

• Tried and true

• Hopeless romantic

• Blissful ignorance

• Kiss of death

• No stone unturned

• 110%

• Take things to the next level

35. Use the em dash. We don’t use it because we don’t know the shortcut for it. The easiest way to write it is to type: -- at the end of a word and then start typing the next word. Our brain wants to press the spacebar after a word with every bone in its body, but treat the two dashes like you do a comma. In Macs it’s shift+option+hyphen. In google docs it’s alt+0151 on the keypad. Absurd.

You can instead go into Tools->Preferences and then say that you want -- to automatically type —

Not sure how to use an em dash?

An em dash is a pause in a sentence.

It’s stronger than a comma but weaker than a semi colon or period.

Also, the em dash draws more attention to a thought than one placed inside a parenthetical. Then again, I try to use the em dash to embolden a point, and I use a parenthetical to sneak one in.

36. Action Verbs.

Precise Verbs. Your action is your everything. Don’t have eyes “look” when they can “shred” or “sag” or “retreat.”

Related: Adverbs are a sign you picked the wrong verb.

Did he run quickly or did he sprint? Did he walk slowly or did he stroll or saunter?

An example: “The sound rattled through the empty parade ground, gouging echoes from the stone.” - Gregory David Roberts from Shantaram

37. Less gerunds.

“When you’re ing’ing, you never actually get anywhere. The passive voice needs gerunds to make anything happen.” Again, Alexander Chee quoting a professor of his, “The verbs tell a reader whether something happened once or continually, what is in motion, what is at rest. Gerunds are lazy, you don’t have to make a decision and soon, everything is happening at the same time, pell-mell, chaos. Don’t do that.”

38. “The adjective that exists solely as decoration is a self-indulgence for the writer and a burden for the reader. Not every oak has to be gnarled.” - William Zinsser

39. Resist using an exclamation point to notify the reader that you are making a joke or being ironic. “It never occurred to me that the water pistol might be loaded!” Readers are annoyed by your reminder that this was a comical moment. They are also robbed of the pleasure of finding it funny on their own. Humor is best achieved by understatement, and there’s nothing subtle about an exclamation point. - William Zinsser

40. Get rid of concept nouns.

"Nouns that express a concept are commonly used in bad writing instead of verbs that tell what somebody did. Here are three typical dead sentences:

The common reaction is incredulous laughter.

Bemused cynicism isn’t the only response to the old system.

The current campus hostility is a symptom of the change.

What is so eerie about these sentences is that they have no people in them. They also have no working verbs—only “is” or “isn’t.” The reader can’t visualize anybody performing some activity; all the meaning lies in impersonal nouns that embody a vague concept: “reaction,” “cynicism,” “response,” “hostility.”

Turn these cold sentences around. Get people doing things:

Most people just laugh with disbelief.

Some people respond to the old system by turning cynical; others say …

It’s easy to notice the change—you can see how angry all the students are.

My revised sentences aren’t jumping with vigor, partly because the material I’m trying to knead into shape is shapeless dough. But at least they have real people and real verbs.

Don’t get caught holding a bag full of abstract nouns. You’ll sink to the bottom of the lake and never be seen again.” - William Zinsser

41. All hell up front; “I can still hear her say it: Put all your deaths, accidents, and diseases up front, at the beginning.” - Alexander Chee

42. “Don’t ever use the word “soul,” if possible. Never quote dialogue you can summarize. Avoid describing crowd scenes, especially party scenes. - Alexander Chee

Along those same lines, don’t use the word, “experiencing.”

““Experiencing” is one of the worst clutterers. Even your dentist will ask if you are experiencing any pain. If he had his own kid in the chair he would say, “Does it hurt?”” - William Zinsser

43. Never write in the passive voice. I used to write like I was apologizing. It's taken me years to get out from under the straight jacket of sorry.

• Bad - “I was writing to see if you were interested.”

• Good - “Are you interested…”

44. “Avoid emotional language. The line goes gray when you do that, she said. Don’t tell the reader that someone was happy or sad. When you do that, the reader has nothing to see. She isn’t angry. She throws his clothes out the window. Be specific.” - Alexander Chee

45. Use the unexpected. Ash Ambirge is one of those writers who doesn’t take one sentence off. One of the things she illuminated was the idea of giving the reader something unexpected. This goes beyond avoiding cliches. It’s more about:

Our customer service is top-notch. (No.)

Our customer service is finer than a three-piece suit. (Yes.)

"Stealing a man’s wife, that’s nothing, but stealing his car, that’s larceny.” James Cain from The Postman Always Rings Twice.

46. Metaphors. How do we tell someone about something that they’ve never seen before? That’s the beauty of language and association. Metaphors use words people understand to describe something they’ve never experienced. So, if I wanted to tell you how stressed someone is, but I really want to hammer the word “stressed,” I can say they are really stressed, or I can come up with a different way to say: really stressed.

What about: His life was more messed up than a pile of hangers.

Other examples:

Olmsted was no literary stylist. Sentences wandered through the report like morning glory through the pickets of a fence. - Erik Larson

The great flat farms of Minnesota are laid out in a ruled grid, as empty of surprises as a sheet of graph paper. - Jonathan Raban

The moon, almost full, was pinned like a medal to the chest of the sky. - Gregory David Roberts

47. "The ear makes allowances for missing grammar, syntax and transitions that the eye wouldn’t tolerate in print." - William Zinsser

48. "Always make sure your readers are oriented. Always ask yourself where you left them in the previous sentence. What do your readers want to know next? Ask yourself that question after every sentence." - William Zinsser

49. Don't start a sentence with "Mr. Smith said."

"BAD: Mr. Smith said that he liked to “go downtown once a week and have lunch with some of my old friends.”

GOOD: “I usually like to go downtown once a week,” Mr. Smith said, “and have lunch with some of my old friends.”

"The second sentence has vitality, the first one is dead. Nothing is deader than to start a sentence with a “Mr. Smith said” construction—it’s where many readers stop reading." - William Zinsser

ON STORYTELLING

50. I’ll leave these to Kurt Vonnegut.

• Use the time of a total stranger in such a way that he or she will not feel the time was wasted.

• Give the reader at least one character he or she can root for.

• Every character should want something, even if it is only a glass of water.

• Be a sadist. No matter how sweet and innocent your leading characters, make awful things happen to them, in order that the reader may see what they are made of.

Godspeed, my friend. All the best in 2020. I hope at least some of these have given you ammo when it’s just you vs. the blinking cursor.