How to Write a Headline Part 2: Figuring It Out

Advanced writing techniques for writer’s block.

Almost three years ago I published an article on how to write headlines using tactics I learned from Suzanne Pope’s “An Inconvenient Truth for Copywriters,” and was happy with how useful people found it.

This is the encore.

Those techniques are basic but effective, and as time went on, I learned how to use more precise and intricate figures of speech and rhetorical devices to improve my writing. I hope these help you too.

There’s a little more thinking involved, a little more rule-breaking, and some “how-to’s” and a list of resources at the bottom that I’ve found to be lifesavers. So let’s begin:

Positively Negative

There’s multiple techniques that you can employ in this tactic from litotes to metonymy to even euphemisms, so I’ll draw them under one common theme — the trick is to highlight something bad to say something good. Draw attention to a downside of the product or service, and spin it using positive affirmations.

One of my favorite headlines of all time does this at an airport in Finland:

A social strategy driving this headline across the internet created quite a stir. Why would you point out your city is miserable if you’re pushing for tourism? Because it makes your tourist awesome.

That brings me to the point that this can be a powerful tool when you’re trying to sell a product or service exclusively meant to appeal to a select type of consumer, rather than the general public. Finnish tourism isn’t on the hunt for a class-trip of 4th-graders. They’re talking to the hardcore adventurers.

My favorite recent example comes from an ad I just saw recently, the new tagline for Boar’s Head Meats, pointing out that their products are expensive, because they’re high quality. With a simple line, they tell us that food is one thing you should never spare expense for: compromise elsewhere.

The message of “it’s expensive because it’s worth it” is a pretty common trend and has been for decades, because this method works. The following ads by Stella Artois highlights that negative aspect with the same spin. They use what would seem like an unfavorable attribute to push a message of superiority.

Wild Turkey used the same idea in a print ad with a little bit of sarcasm to convince you the most negative quality is their biggest selling-point.

How do I use it?

It’s really a matter of creating a cause and effect. Start backwards with the effect, a negative one, and think of a positive reason or quality for it. Make it so bad, it’s good. It’s expensive because it’s worth it. Helsinki sucks in the winter, so going there makes you awesome. The best part about this method is it starts out with the truth, and your goal is to convince the reader to feel better about the hard truth.

Onomatopoeia

This may seem like a bizarre technique to employ in writing, but it is actually extremely effective, and opens so many doors you’d be surprised. Take for example Kellogg’s wildly successful use of onomatopoeia for their classic Rice Krispies cereal, carried by the decades-old slogan that’s still in use today:

The line makes you think about the product in real life, a way to immerse the consumer in their imagination.

What’s convenient about English as opposed to many other languages, is we have a wide array of vocabulary (mostly verbs) that are derived directly from the sound of the action it creates. You can hear the word “slap,” you can feel the word “bang,” unlike the French translations “gifler” and “claquer,” so consider yourself lucky.

By associating a sound or feeling with the product within the headline, you actually get the chance to drive the consumer’s imagination, which is what makes it so powerful.

One of my proudest examples of onomatopoeia is a line I wrote myself a few years back that I’ll humbly throw in here. It plays on an old adage while using onomatopoeia to drive the imagination:

You can imagine the roaring of the engine, especially when coupled with nothing more than a mere product shot. It’s a great technique of expressing something creative when you have nothing more to work with than product shots or stock imagery, because onomatopoeia uses a physical quality of the very product itself.

This technique is as old as time, such as in this Alka-Seltzer ad from ages ago:

There’s even visual examples, such as this Coca Cola print series, “try not to hear this.” The technique is not part of the headline per se, but rather part of the creative idea as a whole:

How do I use it?

The technique here is to simply think of a sound or feeling associated with the product or service, and find an everyday word that is linked with it to employ in your writing. If you already have visual assets such as product photos provided by the client, analyze the images until you can find an onomatopoeia associated with it. You can give the consumer a vision and feeling of using the product. You can drive their imagination by tingling one of their senses with your writing.

Enallage — The Brilliantly Stupid

Enallage is essentially using colloquialism in your writing. The phrase is usually grammatically or semantically incorrect, but done so in a way that just sticks.

Grammatically speaking, they should be “think differently, do you have milk, yes, it’s good.” But none of those are very interesting. However, saying them like you’re talking to your best friend after five bong-hits somehow makes it brilliant.

Bounty uses this with a with a rhyming technique known as a homoioteleuton… forget about that word — point is, it’s so dumb it works.

Interestingly, various state Department of Transportation divisions across the US have employed some creative writers for highway signs, though it has backfired as people are busy taking pictures of the signs instead of driving safely. In any case, I’ll share two here that use the absurd silliness of intentional grammatical mistakes to drive a point.

How do I use it?

It’s tough because there’s no real perfect trick. Maybe try to imagine yourself explaining the product to a stranger at the bar after six mimosas. Or maybe drink six mimosas and try writing anything at all. Or maybe ask a five-year-old to say it for you.

Enallage has a polarity to it; is not very frequent, but exceptionally successful when done right, which is why it’s most often a slogan for an entire brand or product range, as opposed to a banner ad or a tweet. The real trick is writing so casually dumb that it’s just so wrong, it’s right. If you can’t land on one, don’t fret. It’s not the most perfect technique at all, but for some reason has worked wonders for brands.

The Sarcasm Family

There’s different types of sarcasm, from self-deprecating to deadpan to passive-aggressive. They’re all different types of hyperboles in a way, but the point is to write the line to mean the contrary of its conventional meaning, for purposes of humor. We’ll start with general sarcasm before meeting two of its children I employ often, antiphrasis and understatements.

Recently there was a criminal attorney who went viral for his hilarious billboard headline that sums up his claim of exceptional service with a great use of sarcasm:

Obviously you did it. But the sarcasm drives the takeaway message that he can get you out of it.

These two OOH ads for beIN SPORTS use different types of sarcasm. On the left is a satirical insult, while the right leans on the hyperbole with wordplay.

Both Dollar Shave Club and Neutrogena use sarcasm to express that their products work for everyone, everywhere—because of course people have skin and faces, except for the ones in your nightmares.

Sarcasm’s son: Antiphrasis

Antiphrasis is called out here specifically because it requires a very precise construction—explicitly saying the opposite of what you really mean to drive home the point.

Musicbed, a company that licenses music for advertising, called out an icon in the ad industry with a sarcastic message to target its audience of ad agencies by using antiphrasis:

Miami Quality Auto Repair could use a better quality designer, but nonetheless had this banner ad on the Miami Herald’s website for ages that also uses antiphrasis.

Sarcasm’s Daughter: The Understatement

Understatements also deserve a callout because they’re tricky. You would imagine, for obvious reasons, that this would be the polar-opposite of the overstatement, or hyperbole. But upon closer look, it is in fact a different type of hyperbole as it shares something important in common with the overstatement — exaggerating the point for purposes of comedic sarcasm.

Monty Python’s famous line, “it’s just a flesh wound” is a perfect example. The key difference to consider with overstatements and understatements is that the latter sarcastically undermines the product or service, rather than holding it on a pedestal. As counterproductive as that may seem, it works remarkably well. I dug up a spec piece by a fellow classmate years ago for National Geographic’s photography expeditions. I loved it so much I kept a copy of it:

The headlines associate a negative connotation with the service, but in such a humorous way that delights the reader, because we know it’s just sarcasm.

While the typical hyperbole is meant to exaggerate to a point of clear absurdity, the understatement exaggerates with a comedic humbleness.

Here’s a particularly comical one some guy used to sell his car in a newspaper

The intended audience is certainly a DIY-project seeker or maybe a scrap-metal yard. But the understatement is so comical somebody took the effort to circle it, scan it, and post it on the internet. All for just three words.

How do I use it?

For general sarcasm, the key is not saying what you want them to know, and relying on that very intended message being blatantly obvious. The most common pitfall I see with sarcasm is people forgetting that their headline is going to be read, not spoken. So remember that the line will be read at face-value; there is no verbal chance to change your tone to further express the sarcasm. It has to work completely flat.

For antiprahasis, the trick is precisely saying the exact, 100% opposite message, and ensuring that it’s obvious.

For understatements, you just need to go down a road of undermining the message enough that it’s clearly a joke.

That’s the best part of using any form of sarcasm, it never gets old.

The Identical Imposters — Antimetaboles, Antanaclasis, & Chiasmus

The exact definition of each isn’t something to get too bogged down by, but I name them just so they have their names. You can sum up these techniques as a form of parallelism with one unique attribute in common: they create two different meanings with a repeating word or phrase.

Again, forget about the ridiculous terminology. Just read through these examples and it will all come together.

Porsche did a great job in a mere banner ad to push two different messages with the same words using chiasmus:

Alcohol brands offer so much inspiration for writing, as Schaefer Beer and Jack Daniels have done here with these techniques:

What you’ve just seen are antimetables and chasimus, which require a perfectly-reversed second-half to balance the first. For the wildcard antanaclasis, you just need to use the same word or family of that word twice, but you can toss them anywhere in the sentence—as long as it means two different things.

Coca Cola has found some success using antanaclasis because they’ve gone with the same idea multiple times since the 1950’s:

The Washington Post pushed their paper for years with the following slogan that brilliantly says the same thing twice objectively, while saying two very different things subjectively.

Do you get it?

If you get really strong with this method, you can go further and take something so well known to reference, the first line is written in the consumer’s head rather than in the line, such as this headline from The Economist and the brand slogan for Adidas:

Despite the complex names of the rhetorical devices, their methods are powerful tools in writing, because they are so easily memorable.

How do I use it?

It’s tricky to get it to work, but it works well as a trick. That previous sentence is a fair example.

My advice is that you must find two words or combinations of words that compliment each other. There has to be a relationship to each and the product. They can be cause and effect such as the Schaefer example above, or descriptive qualities about the product such as Jack Daniels and Porsche. Or they can just be a word or phrase that carries the entire brand message, such as “go” or “get it.” But the most important part is that the repeated part must carry a different meaning.

A trick I suggest you keep in mind is however you write them, in the middle you need to keep the words connecting them simple and brief, i.e., “to do, to be, to have, the, is,” and so on.

Now you have your words, put together a sentence, then find a way to flip them in the second part of the sentence, word-for-word or slightly differently, until you have a coherent and interesting message.

A final list of resources

Those are the most precise techniques I can offer today without going down a rabbit-hole of linguistics. So I’ll wrap this up.

I’ve also found over the years that a lot of writers have a fantastic ability to pull most of this out of thin air. But some of us really just need some help gathering words. With that said, here are my five favorite resources for writing:

• PowerThesaurus — far more useful than any other thesaurus website out there. It’s open-source and subject to voting, so the list of synonyms only grows and grows.
• Idioms by TheFreeDictionary — looking for a phrase, expression or everyday saying as a starting point? Type any word you’d like to use into this website, and marvel at the wonderful archive of every known phrase in English related to it.
• RhymeZone — I’m including this not because I think rhyming is a great idea (I prefer it as a last-resort) but the filter option on the right offers so much more use. Much like the idioms resource above, you can use a word and search for phrases, homophones, anagrams and more on RhymeZone.
• WordFinders — if you’re trying to work with alliteration or rhyming, WordFinders will help you discover words that start or end with a letter or any number of letters. Maybe you want to look for words that start with “GEN” to go along with your product name or feature. Well, you have “general,” “gentle,” “genuineness,” and 281 more.
• ThoughtCo — a great educational resource for everything, including many more complex rhetorical tactics, advanced grammar, semantics and linguistics. Exciting, right?

These techniques seem complex, but they work. They’ve been around for eons, from Shakespeare’s plays to Mark Twain novels, to Taylor Swift lyrics and presidential speeches. They’ve helped me meet 30-minute deadlines and successfully pitch great campaign ideas that were dismantled by the client.

You may scroll through some of your previous writing and discover you’ve used some of these without even realizing it. But when you put a definition behind a technique, it will help you use it more in the future when you really need something good.

That said, I have three deadlines to deliver by 6PM, so I’ll end it here. Good luck!