How to Write a Better Headline Than This Piece of Shit — Part One

5 min readJun 27, 2017

The lessons that follow I learned the hard way — so you, dear reader, don’t suffer the same fate.

Taking the hard line sucks. But it works.

Without mentors like Bob McKee, Mark Swanson and Dave Bour, I’d have very little to say on this topic (or any other). So thanks, fellas. Mean it.

Your entire screenplay, campaign, beat or novel runs on one good idea. But great themes are hard to nail. A lot’s at stake. Because there’s no way your print ad, breaking story or think-piece survives in the wild without an extremely provocative sentence at the top.

Especially when every member of “the wild” actively avoids you and your lame distraction, it takes one hell of a collision to jar something loose.

Writers are in the epiphany business. Our job is not to write; it’s to provoke. We have to draw the first three quarters of a circle so readers can cognitively close the loop.

Headlines work when they create an “Aha!” moment that rings a bell. That’s why our chosen language must ask a question the reader hasn’t considered and provide an answer they didn’t expect.

But the thing about answers is, they gotta be true. By that I don’t mean saying something true — I mean telling the truth.

Truth is not about facts. Telling the truth is revealing the secret to why it happened. It’s about coming clean, not reporting.

All writing is fiction. There are a million true things you could report about any scene and a trillion angles from which you could tell the story. Facts are merely an outline; truth fills in the color.

The truth is the secret to why.

Forrest Gump tells the truth. The Weather Channel reports facts that are true. Journalists synthesize both.

If that sounds like crazy sorcery, let’s dissect a live one. I wrote the following for the U.S. Army in Sept. 2016.

Thought leadership happens in that order.

(implied) question: what’s real leadership?

(unexpected) answer: thinking the hardest.

I like this line a lot — it passed my test, but hit a snag in the Land of Clients and didn’t end up seeing daylight (’til now, suckers!). But while we’re here, I should mention that this happens more often than it doesn’t. Sometimes it’s for a terrible reason, other times it’s not even for a reason.

In this case, the lieutenant colonel on the other end liked the sentiment, but said it contradicts what the Army teaches. They believe leadership is a behavior that always precedes thought, and leaders are those who harness behavioral discipline to control their thoughts and reactions.

Such an incredible answer. Sure, he said no — whatever. Happens.

But he gave incredibly valuable information about their mindset that I can actively use moving forward. We all learned one of the foundational guiding philosophies driving the thought process of perhaps the most powerful organization in the history of planet earth.

I mean, I could mention that the science is firmly on my side, and I could try to “win” the argument. But there’s no prize for winning — you’re trying to persuade. The most persuasive thing an artist can do after receiving negative feedback is to take the baton and sprint full speed ahead.

Because you didn’t do it for them. You did it for it. Right?

(That’s why I’m definitely not keeping track of every client I ever disagree with in a hidden word doc I named “2003 Taxes”)

Pretend like you embrace rewrites. Big picture, they’re always good. You get to have another idea and keep the old one since nobody wanted it. File that beast in the cabinet and come back to it.

You can tell exactly how good an idea (headline) is by how well it holds up once you rewrite it. Told a different way, good ideas are still good ideas. Each time you change its form, you learn more about its function. I found out exactly how heavily I leaned on the language choices (instead of the idea itself) once I stripped it down for a rewrite.

Here’s how our party ended:

Is that line weird for you? It’s a little weird for me. I dunno, maybe I’m overthinking it.

Point is, it’s hard to distil a hairy, unrinsed idea into a single sentence. But it’s also necessary work that very few folks do well.

All of us — copywriters, ghostwriters, screenwriters, journalists, poets, YouTube commenters, Redditors, Twitter-governors and other professional writers — we all sell the same promise: here lies a good story, well-told.

Start there: a headline (whatever its purpose) must suggest inside this box they’ll find the story they long for — and you’re just the girl to tell it. But unless the headline strikes a nerve, who wants to read your shit? Hint: no one.

Before we dissect that nerve, let’s go over what this isn’t.

Writing is not about words.

Writing is not about words any more than your favorite movie is about dialogue.

I wish death to all formulaic click bait headline templates.

You know, those annoying pieces of shit that always go something like “Top 3 ways to fix all your problems. Number 2 will SHOCK you!” or “The ONE Weird Trick Doctors HATE!”

We can smell fishy formulaic click bait from the elevator. Don’t add your fuel to the dumpster fire industry of tricking people into clicking.

‘Care’ is the special sauce. If you care, you have fuel to create.

Instead, mine deeper into your emotion of disdain for the trickery—it might be great source material for a joke, an idea or a construct. Writing becomes art when an emotion is expressed intellectually.

For example, in college I got fed up with the intellectual laziness most copywriters display and thought it was ruining the world (I had a flair for the dramatic). I felt it was unfair how the medium I planned to work in comes across as deceptive and untrue as a result of so many idiots being lazy with their words.

So I made a spec ad that satirizes the scumminess of ads. Soon after mocking the industry, I graduated ad school and and worked in advertising to this day.

Call it adsterbating, if you will.