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Don’t Press Send: The New Rules for Good Writing

Entertain, don’t be afraid of a bit of filth, but be cautious with your XXXs – the essential guide to getting your message across while avoiding the pitfalls of communication.

The Guardian

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Illustration: Stephen Collins

Letters of Complaint

The person who gets your letter will seldom be the one who wronged you. At least to start with, they have no skin in the game and may even be sympathetic. That evaporates when you start slinging around insults. It makes you feel good to bluster and rage: but it’s how the recipient of the letter feels that will matter. As ever, go to where your audience is.

Picture how your letter will go over when Dave in Customer Relations reads it out to Jane at the next desk. Dave almost certainly doesn’t give a monkey’s. The more blood-curdling the letter, the more likely they’ll have a good giggle and start thinking up ways to make you angrier. Start from the assumption that you are entertainment; and then work to countermand that. Ideally, Dave reads your letter to Jane and she goes: “You have to admit that person has a point …”

Make irresistibly plain how you’ve been inconvenienced, then propose what’ll seem to your correspondent a reasonable and proportionate redress – and one within their power to make. So be forensically clear: what are you complaining about, and what do you want to happen? When you’re proposing redress, “I demand” is – oddly – a lot easier to ignore than, for instance, “It seems reasonable to expect …” Remember Hotspur and Glendower in Henry IV, Part One? “I can call spirits from the vasty deep,” Glendower brags. “Why, so can I, or so can any man,” laughs Hotspur. “But will they come when you do call for them?”

Take your correspondent gently but firmly by the elbow, rather than bashing heads. Once an exchange gets oppositional or abusive, it will stay that way. I’ve been let off parking tickets by writing politely and apologetically to the council to explain the circumstances. I’ve never got anywhere by calling someone a jobsworth.

Letters to Friends

One of the saddest things for me as a literary journalist is the realisation that the Collected Letters, as a genre of published book, is almost certainly dying out. But if you read the great epistolary friendships – Robert Lowell and Elizabeth Bishop, say, or Kingsley Amis and Philip Larkin – you will see what we have lost. In our letters we are doing what Hazlitt called “writing to the moment”: the quick of life is in them, and all its absurdity.

That sense of a lifelong conversation comes poignantly through in the last letter from Larkin to Amis. Dictating from his deathbed, Larkin ended his last letter to his friend: “You will excuse the absence of the usual valediction, Yours ever, Philip.” Every letter that he’d sent Amis for decades had ended in the word “bum”. But out of consideration for the sensibilities of the woman who’d be transcribing his tape, Larkin omitted it. Eleven days later he was dead.

Always remember that your job, writing to a friend, is to entertain. That can mean revelling in the odd pratfall. In London Fields, Martin Amis offered the best postcard-writing advice I’ve ever read: “The letter with the foreign postmark that tells of good weather, pleasant food and comfortable accommodation,” he warned, “isn’t nearly as much fun to read, or to write, as the letter that tells of rotting chalets, dysentery and drizzle. Who else but Tolstoy has made happiness really swing on the page?”

Letters of Condolence

There is little that paralyses the average person more than writing a letter of condolence. You feel awkward and embarrassed. That’s fine. The act of writing is in itself what will be valued: you are extending respect and friendship. Write quickly, and write – I’d strongly suggest – by hand.

You’ll want to calibrate what you write to your relationship both with the recipient and with the deceased. The whole point of this letter is that it’s personal. If you knew the deceased well, sharing a couple of warm memories – even funny ones – will let the recipient feel there’s a shared bond. If you didn’t know the deceased, you will probably be able to make respectful reference to what you knew of them.

And take care. Julian Barnes’s 2013 book Levels of Life – which includes a memoir of his loss of his wife to an aggressive form of cancer – describes with unusual candour how the person grieving can feel anger towards friends “for their inability to say or do the right things, for their unwanted pressingness or seeming froideur. And since the grief-struck rarely know what they need or want, only what they don’t, offence-giving and offence-taking are common.”

Use tact. Don’t be bossy. Don’t tell the recipient how they should be feeling. If you’re finding it hard to know what to say, you can acknowledge that; but don’t harp on it. “I’m finding this a hard letter to write, but I want you to know that all my thoughts are with you,” or something like it, is fine. Absolutely to be avoided are operatic, or competitive, expressions of grief. Acknowledge, but don’t belabour, the dreadful grief and pain that the person must be feeling. You’re trying to focus on the individual excellence of the person they’ve lost rather than the consequences of the loss itself.

Also, a respectful tact with regards to matters of religion is advisable. If you write to the widow of a die-hard atheist – even if you yourself are a believing Christian – saying that you’re certain he’s in heaven right now crosses the line from condolence to trolling. It’s not about you.

Love Letters

There are as many potential love letters as there are lovers. And as Cyrano de Bergerac showed us, the right words can win the girl even when the boy’s nose is disfiguringly enormous and she would totally swipe left on Tinder.

The love letter is about attention. I’ve heard it said that what makes a relationship work is not how you feel about the other person, but how they make you feel about yourself. Here is the essence of the performance: you’re demonstrating a special quality of attention. You’re being your best self – most alive to the world, most engaged with the other – so that the attention you’re paying to them becomes a fantastic compliment.

A lot of Fotherington-Thomas guff about moonlight and roses and whiskers on kittens is unlikely to work: you’re supposed to be intoxicated with your lover, not with your own prose style. When William Godwin was courting his future wife Mary Wollstonecraft, he sent her a stilted love poem. She responded sharply that she didn’t want an artificial composition but a “bird’s-eye view of your heart”. She told him not to write to her again “unless you honestly acknowledge yourself bewitched”.

Also, there’s no harm in a bit of filth. Look at Hughes to Plath, or Joyce to Nora Barnacle. Sex is intimate; so is communication about sex.

Writing for Digital

Any number of linguistic and ideological tribes mix and clash in cyberspace, so it’s no surprise that the internet in general and social media in particular are great laboratories of language change. Imagine the difference between patiently studying evolution through the fossil record, and then moving labs to work on Drosophila melanogaster. A fruit-fly generation is not much more than 10 days long: suddenly, you can study evolution in real time. Same with digital media: usages come and go in a matter of months.

The mashing up of genres and categories is characteristic of the way we read online. Even when we’re reading a serious essay, we might well have several other windows open. We’ll be checking our phones, alt-tabbing to Twitter, idling through party photographs on Instagram. So digital writing is about getting and retaining attention.

You’re aiming for clickiness and stickiness. And we do know, roughly, what travels online. Pictures go further than text alone. Emotional content – anger, humour, curiosity, astonishment – is particularly effective. When I interviewed BuzzFeed’s founder Jonah Peretti he argued that memes and web culture in general are “organised by a sort of social logic. What kind of things do people like to do together? What kinds of things do people relate to? We organise our site by these emotional responses.”


Email runs from a digital version of ordinary letter-writing to something much more like a text message, so hitting the right register requires a moment of thought. If you spend all day firing off emails – to your husband one moment and your boss the next – it can be easy to let the registers blur. That fretwork of kisses with which you sign off is fine to a friend; probably inappropriate with a colleague. Remember, as Hillary didn’t, that copyright in emails you write in the office will almost certainly belong to your company, and they’ll be archived indefinitely. Before you hit send, think how would this look raised at an employment tribunal. Better safe than sorry.

Emailing strangers, particularly in a professional context, asks for the same level of formality as a paper-and-ink letter. You wouldn’t open a written letter to a stranger with “Hi Bob!”, and some if not most Bobs will receive such an email with irritation. Friendly is fine; presumptuous is risky.

Flagging emails “urgent” may make sense within a company. To outsiders it looks as if you’re presuming to jump a queue. Email’s virtue is to combine immediacy of communication with the courtesy of letting people respond in their own time. If someone feels you’re forcing yourself on their attention, they won’t like it. Requesting a read receipt is a jabbed finger in the chest. If you need a quick response, make it clear in the email itself.

Social Media

Social media present perils and opportunities. The opportunities are that they have a potentially limitless reach: you can reach the world from your laptop. They also provide for things to go viral in the wrong way. So here are three cautions:

1) Tone often fails to travel online. Irony, self-mockery or dark humour can easily be parsed as bigotry. A question can be parsed as a sneer – hence the rise of the defensive formula “genuine question”. You only have to look at the so-called “Twitter storms” that descend on quite innocent individuals to see the hazards.

2) You have multiple potential audiences. Your potential overhearers may not be as sympathetic to you as your friends or followers. This point is closely allied to the first. Think about what certain behaviours might look like if they were spread more widely. The safest assumption to make is that even ostensibly closed social media sites – Facebook or a locked Twitter account, for example – are essentially public forums.

3) Stuff never, ever disappears from the internet. It really doesn’t. You can delete a tweet or take down a Facebook page or edit an Instagram post, but some bastard will have it screencapped. Drunk-texting can be a mistake; posting on social media drunk – and/or in anger or self-pity – can be a catastrophe. Post in haste; repent at leisure.

And don’t always be on transmit: social media are set up for conversation. Ask questions. Respond to people. This goes just as strongly for corporate accounts as it does for personal ones.

The tone of voice you use will set the tone of the conversation. Fury tends to invite fury. Reasonableness tends to invite reasonableness.

Be funny, if you can: if you make somebody laugh, you have them for life. A few years back the not-especially-well-known novelist David Whitehouse tweeted: “Lance Armstrong should be applauded for riding a bike so well on drugs. I tried it once. Hit a dog and fell into the canal.” It earned him nearly 10,000 retweets.

Reposting praise turns people off; only repost insults and abuse. People enjoy reading those more in any case.

Remember that – whether you live in a country blessed by the first amendment or not – the laws of libel apply to you, and that repeating a libel is itself a libel. “Interesting if true” or “*innocent face*” don’t make you immune to being sued. Being “in the know” makes you feel good. Being “liable for exemplary damages and the other side’s legal costs”, not so much.

Above all, respect the first rule of the internet: “Don’t be a dick.” Unless that’s your express purpose, in which case knock yourself out. But be prepared to take the consequences.

Five Simple Ways to Engage and Convince Your Reader

1. Bait the Hook

Call it audience awareness, call it decorum, call it reader relations if you like, but the key principle of all persuasive writing is customer service. I’m fond of a quote – variously attributed – that says: “When you go fishing, you bait the hook with what the fish likes, not with what you like.” An obvious principle, easily lost sight of.

Putting yourself in the audience’s shoes governs everything from the shape of your argument to the choice of vocabulary. Ask what they do and don’t know about the subject, and what they need to; not what you know about it. Ask what they are likely to find funny, rather than what you do. What are the shared references that will bring them on board? Where do you need to pitch your language? How much attention are they likely to be paying?

This is what Aristotle, talking about rhetoric, called ethos, or the question of how your audience sees you. And the best way for them to see you is either as one of them, or someone on their side. As the speech theorist Kenneth Burke wrote – another line I never tire of quoting – “You persuade a man only insofar as you can talk his language by speech, gesture, tonality, order, image, attitude, identifying your ways with his.”

2. Be Clear

A lot of style guides, with good reason, tell their readers to write Plain English. There’s even a Plain English Campaign that does its nut, year-round and vocationally, about examples of baffling officialese, pompous lawyer-speak and soul-shrivelling business jargon.

Plain English (the simplest word that does the job; straightforward sentences; nice active verbs etc) is far from the only style you should have at your command. But if you depart from it, you should have a reason, be it aesthetic or professional. The plainer the language, the easier the reader finds it; and the easier the reader finds it, the more likely they’ll take in what you’re saying and continue reading. Surveys of the average reading age of British adults routinely put it between nine and 13. Trim your style accordingly.

Steven Pinker talks about “classic style” (he borrows the notion from the literary critics Francis-Noël Thomas and Mark Turner). This, as he sees it, is a variation on Plain English that compliments the reader’s intelligence and talks to him or her as an equal. He gives a cute example. “The early bird gets the worm” is plain style, he says. “The second mouse gets the cheese” is classic. I half-buy the distinction; though much of what Pinker credits to the classic style is exactly what’s asked of any good instance of the plain. And the examples he offers convey quite different thoughts, and (a bit unfairly) attribute a cliche to the plain style and a good joke to the classic.

But whatever you call it, the basic style for non-literary writing wants to put clarity, which usually means simplicity, first. That doesn’t preclude jokes, metaphor or any sort of playfulness: it just warns that splashes of colour stand out better on a plain background.

3. Be Correct

Entire books are written on this subject every year: this least interesting aspect of language occupies a disproportionate place in the public conversation about it. Are you a pettifogging pedant who thinks that the widespread use of the word “decimate” to mean “annihilate”, or “gay” to mean “homosexual”, is a sign of the barbarism and illiteracy of today’s youth? Do you go out of your way to avoid splitting infinitives, make gargling noises in the “10 items or less” queue, and have strong feelings about the word “whom”? Take a jersey: you’re team prescriptivist. Do you scoff at pedantry, love to use new coinages and loan-words, begin sentences with conjunctions just for the hell of it and think Eats, Shoots & Leaves was a book for the small-minded and ignorant? That end, please: you’re team descriptivist.

The so-called “language wars” give all those involved in them a thrill of opposition, and have done since Caxton was moaning circa 1478 that English isn’t what it used to be. Most of us, as civilians, carry on regardless. I say only this: the descriptivists are, in essence, right. Language changes according to usage and there’s no referee or court of appeal, no matter how noisily some people may volunteer for those jobs. Whatever pedants say, some nonstandard usages will increase not only the expressive range of the language and its precision (Belfast “youse” or Louisiana “y’all” introduce a number distinction not present in standard English, for instance), but often its beauty.

But a feature of what we please to call standard written English is that many of its users place a premium on “correctness”, or the idea of it. Hence, on the baiting-the-hook principle, getting it right – or, if you prefer, “right” – is worth doing. You may frame it as a stylistic preference, as a way of showing off a conventional education and implying intellectual authority, or simply as throwing a bone to the pedants in the audience. But if you’re writing in a formal situation you’d be best to err on the side of not erring.

4. Prefer Right-Branching Sentences

Your audience has a limited attention span and limited brain power. So don’t write, if you can help it, sentences of the sort that caused Clover Adams to say of Henry James that he chewed more than he could bite off. This doesn’t necessarily mean you should write only short sentences. It’s more to do with sentence structure. A preference for what American linguists call “right-branching” sentences eases the cognitive load.

Standard-issue sentences, in English, have subject-verb-object order: dog (subject) bites (verb) man (object). There are any number of elaborations on this, but the spine of your sentence, no matter how many limbs it grows, consists of those three things. (Or two if your verb, like “sleep” or “disappear”, doesn’t take an object.) Don’t lose sight of it.

If you have a huge series of modifying clauses before you reach the subject of the sentence, the reader’s brain is working harder; likewise, if you have a vast parenthesis between subject and verb or even verb and object. The reader’s brain has registered the subject (dog) and it is waiting for a verb so it can make sense of the sentence. Meanwhile, you’re distracting it by cramming ever more material into its working memory. “My dog, which I got last week because I’ve always wanted a dog and I heard from Fred – you know, Fred who works in the chip shop and had that injury last year three days after coming home from his holidays – that he was getting rid of his because his hours had changed and he couldn’t walk it as much as it wanted (very thoughtful, is Fred), bit me ...”

As often, TS Eliot shows us how not to do it: “In the uncertain hour before the morning/ Near the ending of interminable night/ At the recurrent end of the unending/ After the dark dove with the flickering tongue/ Had passed below the horizon of his homing/ While the dead leaves still rattled on like tin/ Over the asphalt where no other sound was/ Between three districts whence the smoke arose ...”

“Whence the smoke arose WHAT, already?” the reader wants to shout in his best Larry David voice. This sentence (it continues: “I met ...”) is a whole lot of gong and no dinner. Beautiful it may be – but it’s hard work on the reader. If you’re not writing “Little Gidding”, do it the other way.

5. Read it Aloud

It is almost impossibly hard to write, formally, about cadence – the term usually given to the rhythms of prose. When you’re writing about poetry (or, at least, formal verse) you can point to a line and identify it as an iambic pentameter, a trochaic tetrameter or a catalectic hexameter in amphibrachs, as the case may be. But prose rhythm doesn’t work like that: it’s irregular. Nevertheless, it’s also extremely important.

The formally learned skills of reading and writing come from the informally learned skills of speaking and hearing. Such neuroscientific work as has been done on language shows that when we read, we’re activating areas of the brain associated with sound. You “hear” even when you’re reading silently. The reader has an internal ear: so must the writer. Read a lot and write a lot and your ear will improve.

Most of what gets described as “good writing” is so described because – one way or another – it sounds right. It flows when it should flow and slows when it should slow. The stresses fall naturally on the words that the writer wants to emphasise. The reader doesn’t stumble over an unintended internal rhyme or a clumsy repetition. Reading something aloud is a good way of stress-testing it: you’ll notice the rhythm more. Also, you’ll notice very abruptly if your sentences are tangled up: that overfilling-the-working-memory thing can be heard in your voice. The American speechwriter Peggy Noonan advises that once you have a draft, “Stand up and speak it aloud. Where you falter, alter.”

Sam Leith’s Write to the Point is published by Profile.

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This post originally appeared on The Guardian and was published October 7, 2017. This article is republished here with permission.

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