7 Deadly Headline Sins Every Copywriter Must Avoid

Originally published at www.judyolbrych.com.

I stuck close to the elbow of my guide. Claude, an eminent copywriter in his past life, had been assigned to lead me to the perfect headline, and I was in no shape to venture out on my own.

We’d been trudging through the basement all morning. The damp passageways were littered with the remains of multi-level marketers. Fake twitter profiles hung on the walls as we passed cages inhabited by timeshare representatives. They were bound together, trapped in an eternal sales presentation they would never escape.

Suddenly, a ray of golden light pierced through a window, warming our weary limbs.

A luminous structure towered against the skyline — a seven-floor library. Shadowy forms moved past the windows. A glass elevator shaft hugged the walls, its brass railings appearing to grow brighter as it ascended to each level.

After hours of walking, we were famished. Claude announced that afternoon tea would be served when we arrived at our destination.

We stepped into the elevator. “Level One,” buzzed a genderless electronic voice, and the doors opened.

Level One (The Wrong Offer)

Dusty tomes stood in stacks like hay bales in a barren field. We stepped through a scattering of rusty bookbinding needles and across pitted marble to a small café.

”Have a menu” said Claude.

“Thanks, I replied,” then gasped as I looked at the specials. Candied eel, boiled okra, ink-blot soup … not feeling hungry anymore.

“Nothing appealing to you?” asked Claude. “How about the marshmallow oysters? Or a refreshing gin and printer-toner?”

“Not so much,” I replied “Hey, what’s happening here?”

“This is where people are surrounded by the most exquisite delights — all day, every day. But no-one is ever satisfied. And those who have presented the wrong offers in their headlines must do penance listening to unhappy readers. It is only after they’ve collected copious data that they may advance to the next floor. Come and see.”

We followed a weary writer back through the stacks as he deposited a bulky volume and entered the elevator.

Emblazoned over the elevator doors glowed the words:

“Sell people what they want to buy.” — Gary Halbert

Level Two (Failure to Identify Your Customer)

As the doors opened, we found ourselves in a new café and surrounded by lush green plants. Ivory candles and white linen adorned each table. A waiter handed us menus. Prosciutto and melon, roast beef au jus, filet mignon, cherries jubilee …

“Now we’re talking, Claude. Let’s order. I’ll have the French onion soup, the asparagus and gouda quiche, and baked Alaska.”

“Very well,” replied the waiter and he left.

After what seemed like a short moment, he returned. “Your broccoli chowder, Madame”

“Broccoli chowder? But I ordered French onion soup!”

“Ah, there must be some mistake. Just a moment, and I will return with your chowder.”

He soon came back with a tray of steamy hot onion soup and delivered it to a neighboring table.

The couple looked up in confusion.

Our attendant returned shortly with a new bowl. My tummy rumbled, and my mouth watered explosively in anticipation.

“Your broccoli chowder, Madame. Bon appétit.”

“There must be some mistake …” I replied, as he turned away.

“No mistake here,“ replied Claude. “On this floor, all copywriters are doomed to serve the wrong people. The only way past certain unhappiness and business failure is to identify your true customers.”

Ahhh! But what’s this I see?

Our waiter now held a small crock overflowing with melted white cheese. The pungent odor of onions and Thyme wafted across the table.

We suddenly found ourselves in the elevator with our waiter. He stood at our side and exhaled in relief.

Muzak piped faintly through the speakers. The words over the doors now read:

“The headline is the ‘ticket on the meat!’ Use it to flag down readers who are prospects for the kind of product you are advertising.” — David Ogilvy

Level Three (The Copywriting Selfie)

As the doors re-opened, a scuffle of activity drew our gazes to the floor.

Writers stooped, bent, and crawled over a succession of mosaics. Each piece illustrated a scene from the ancient tale of Narcissus. The handsome demigod had been so enchanted by his own reflection in a pool of water, he had died of heartbreak after failing to attain the object of his affection.

“Where are we?” I asked a copywriter as he slithered by. The knees of his jeans were worn through with holes, and the elbows of his once-crisp white oxford were getting dingy. His nose was pointed to the floor. His head was frozen facing downward.

“For many long months I’ve crawled and labored here,” replied the writer. “We’ve all committed copywriting selfies. I’ll remain in limbo until I learn to replace “I, We, and us” with “You and Yours” in every corporate newsletter mailed since 1972. Farewell, dear friend …” He picked up a vial of White-out and made his way toward a crowded desk.

“How would YOU like to go the next level?” I asked Claude.

That’s the perfect question,” he replied. We turned toward the elevator.

Next the doors hung a sign:

“No one cares about you. They care about themselves” — Neville Medhora

Level Four (No Benefits)

My legs weakened as we rose to the next floor. The aroma of grilled cheese and fries drifted our way, bringing the promise of the long-awaited lunch.

We wove our way past empty lunch tables and men with brooms. Hundreds of copywriters waited and fidgeted in long, tortuous lines. A stream of writers moved perpetually from one line to the next in search of a shorter queue.

“They say the other line always moves faster,” remarked a petite blonde as she joined us. But who has the patience?”

“How did you end up here?”

“Direct order from a minor deity at Google … my headlines had no benefits. Good thing I added metadata, or I’d be sweeping the floor. Now, I’m doomed to stand in these lines forever until I offer someone — anyone — their greatest wish. Want to get out of here?”

“Psst!” signaled Claude, and we were all transported to the familiar sliding doors.

“Going Up!” A tinny voice crackled over the loudspeaker. And then:

“Consumers do not buy products. They buy product benefits.” — David Ogilvy

Level Five (Useless words)

The elevator lurched to a stop and we tumbled into a mound of boxes, files, and yellowing catalog cards. Silent workers pushed carts of unsorted books. Others in orange jumpsuits stabbed papers with long pointy stakes and bagged them in a futile attempt to clear the mess.

“These copywriters have littered their headlines with useless and impressive words. The only way out,” explained Claude, “is to ascend the inner staircase. Discard the surplus and find the way.”

We each received a sack and began to stab our way to the steps

Each step bore a single phrase of this quote:

“Make it simple.

Make it memorable.

Make it inviting to look at.

Make it fun to read.”

– Leo Burnett

Level Six (No Urgency)

“Sixth floor,” announced our guide.

Groupings of white sofas and pastel chaise lounges surrounded tables laden with caviar and champagne. A large screen covered the inner wall. We discarded our bags and entered.

The sweet tones of a marimba played as a bartender glided past us with a tray of umbrella-topped mojitos. Writers lounged in eerie stillness, their glazed eyes staring straight ahead.

The mojitos, champagne and caviar remained untouched.

“What’s wrong with them?” I cried. “Why won’t they move?”

“There’s no reason to move now when they can partake later,” replied Claude. “Besides, they’re about to show a Game of Thrones replay on the big screen …

There’s no Urgency”

I felt myself beginning to slip into a zombie-like trance until …

“Last call for the seventh floor.” A voice jolted me awake.

We grabbed mojitos and ran to the elevator just as the doors were closing

As we passed the movie screen, the words flashed:

“Nothing works as well on the web as deadlines” — Clayton Makepeace

Level Seven (Not Specific)

A blast of humid warm air enveloped us as the doors opened one last time.

Tropical plants bloomed brightly among the book stacks. Orchids and heliotropes released their wild perfumes. Neon-colored parrots squawked. Each table was crowded with copywriters taking detailed notes from books piled high on every surface.

“These copywriters were not specific in their headlines,” explained my guide. “Now they spend their days and nights in research. You must

Be specific!”

A uniformed guard blocked a single escalator to the rooftop. He was built like a marine and armed.

“This is our last passage,” explained Claude. “Find your way to the roof top, and your headlines will irresistible. But first, you must solve the riddle.”

“Animal, vegetable, or mineral,” offered the guard.

“Um … vegetable?” I guessed.


“Is it green?”


“Is it carnivorous?”



“That’s a Roman goddess,” warned Claude. “Remember, be specific

“Venus Flytrap!”

The guard shifted to one side and the escalator cranked up to a rapid speed. We hopped on with an exuberant leap and ran to the top.

Daylight flooded our eyes. Copywriting legends David Ogilvy and Gene Schwartz stood before a tray piled high with sandwiches.

“Liverwurst or Pastrami?“ offered Ogilvy …

Before I could answer, I awoke with a jolt.

I was sitting at my desk and had slept through lunch.

Time to write the headlines …

Want to know more about how to write a headline? Grab my cheat sheet for getting unstuck and writing high-conversion headlines in minutes.