One of the Web’s unique aspects is the sheer number of voices contributing to the conversation. Even in news stories from well-known sources, everyone seems to have a different approach.

Actually, that’s not true at all.

Most people seem to see an approach that appears popular, and endeavor to copy it as closely as possible.

Hence, clickbait begets clickbait, given that well-written headlines are far more challenging to duplicate.

This entry will help you take a few steps to remedy the imitative tendency and find your own voice when writing headlines.

Learn Your Limitations So That You Can Overcome Them

As you know by now from reading this blog, I write. In fact, I’m taking a break from writing something else in order to get this set of ideas out of my head — so that I can get back to work on that other piece of writing. I don’t call myself “a writer” because “Hi, I’m a writer them”-types tend to talk, drink coffee and pose in trendy cafes rather than actually writing anything.

Still, despite a lifelong lust for words, it took about a year to learn how to “feel” a headline and flesh it out quickly and painlessly. Luckily, I do love to write, so wrestling with a prickly headline is more fun than playing peek-a-boo with a two-year-old. Compared to a novice, I’m an expert. Compared to a mastermind, I’m a tadpole.

These are notes, written as much for me as for you.


Keep reading if you want to gain some tidbits of what I’ve learned thus far. Save yourself from the typical road of wasted time, duplicating my past mistakes in your own experience. The tips below can help shortcut your journey toward becoming a decent headline-writer. This is a skill whose value becomes ubiquitous in a world increasingly dominated by clickable links and attempts to monopolize an ever-diminishing slice of the reader’s attention.

Who knows, it might even help you write a better online dating profile in time for next Valentine’s Day.

Know Your Audience

Two points stand out in regard to audience selection: subculture and smarts.

1. Seek the Subculture
Did you notice that I mentioned Valentine’s Day in the previous section? That’s because you probably know of it, even if you don’t celebrate the holiday. Your headlines will likewise need to match the cultural and/or subcultural tastes and niche knowledge of the intended reader.

2. How Smart Are They?
If your audience is an “intellectual” group, you can write smarter headlines.

It’s also likely that your audience will be a group of chuckle-seeking dummies (see: any comment section beneath a cat picture). The Internet is brimming with Chuckleheads, like crabs in a barrel. They generally will accuse you of being “elitist” or “trying to sound smart” for using multisyllabic words, metaphors or anything less blunt than chalk etched into a brick wall.

If you’re dealing with dummies, you’ll have to dumb down your prose to their level.

Rule of thumb: when in doubt, dumb it down. Even “intellectual” people often have their smarts set to the “off” position much of the time.

You’ll see more about how to turn on the right type of reader a bit farther down.

Shape Your Headline

Should you give the reader: A) a tantalizing tease of what’s to come, or B) give a broad overview and hope that it whets their appetite for more?

If the headline describes a piece that takes a position (“the newest installment of Star Wars will be the best ever”), know that many Chucklehead-types will nod along, comment, Like, Favorite and upvote (or downvote) without bothering to read the piece itself.

Entire discussions can arise based on people’s assumptions and preconceived opinions.

General rule: give the reader enough information to entice him or her to find the rest by clicking on the link.

This leads to the 800-pound Chewbacca hiding in the corner like Sia singing at the 2015 Grammy Awards (I always wondered what Chewbacca’s knees looked like from behind… somewhat slender when well-shaven… but I digress): how to avoid clickbait purgatory?

Ways To Avoid Clickbait Purgatory

0. Avoid the impulse to include hammy stylistic flourishes.

Eschew eyeball-grabbers that smell like a Gawker affiliate (io9 and Jezebel are probably the best-known) or the Huffington Post.

This one is actually tricky because some of those techniques are great organizing devices for articles. For example, using bullet-points (“Five Reasons Why Minestrone Is The Best Comfort Food Ever”) can be useful. If bullets are all you’ve got, though, the article or blog entry may need more substance — or it may simply be unfinished.

The more practice you have at avoid hammy headlines, the more space you’ll give your mind to be creative.

1. Define your goal

If you want the typical reader (who will Like/upvote/etc. a headline without bothering to read the rest), state an unsubstantiated opinion as a fact.

Example A1: “Believe The Hype: Bill Cosby Is A Rapist Because Some People Say So And Some People Are Women.”
Example B1: “Five reasons Why Yoda Has More Fabulous Hair Than Luke Skywalker”

If your goal is to give the reader a reason to read beyond the headline, give information that opens a more interesting question in the reader’s mind. This question will only be solved by clicking through and reading more.

Example A2: “Bill Cosby and the folly of crowds: How many rape accusations are needed for the Internet to convict a celebrity on heresay alone?”
Example B2: “Yoda was the mentor that Luke lacked, reflected even in the character’s choice of hair versus Darth Vader’s impenetrable helmet. Explore the design of Star Wars’ most inscrutably beloved characters.”

In some formats, headlines like these may be split in two by a subhead. Note how they start a story that can only be finished by continuing to read.

2. Write a longer headline

This goes back to the question of “knowing your audience”. Generally speaking, I select intelligent readers by screening out the dummies through the use of longer headlines.

People suffering from Internet Attention Deficit Disorder (also known as ‘Chuckleheads’) will generally misread and misinterpret regardless of how well you craft your headline. From them, you’ll hear such excuses as “I skimmed it and got the gist”, “I took a quick look, and this is what I think…”, etc. You can safely ignore the majority of such “skimmers” and “thinkers”, as they merely repeat their talking points at anyone within range.

Solution: find better readers. One way to do that is to screen the good ones in, and automatically weed out the dummies.
How? Write a longer, more literate headline. There is no limit to the length of the headline, so this is a question of the writer’s skill, the chosen format and readers’ tolerance.

See the note below about being “awesome” for a caveat about how not to overdo this screening technique.

3. Take your time

Write several drafts. A headline is the same as any other type of writing. In some ways, the headline is more information-dense than any other kind of prose: you have to say the most in shortest period of time.

The first three drafts will focus your brain on the task at hand and develop the background of related words for you to play with in crafting the finished product. Really play with the words and concepts.

Once you’ve compiled a few test-lines, experiment with condensing the ideas from multiple words to a single one. Combine ideas and trim away extraneous cutesy bits, distracting parts, or words that slow down the eye.

Suggestions For Headline Experimentation

Your eyes and mind should slide across the headline from start to finish. Smooth the words until they flow.

A “melody” of words and “harmony” of the whole will allow the reader to remember the message. Listen for it and learn to feel the rhythms of the spaces as well as the words.

Find a small morsel in the piece itself and magnify it for the headline so that the reader can delight in noticing it for the second time.

Try understating a point rather than screeching it at concert volume.

Use alliteration liberally — then break it or hint at it rather than running on with similar words.

Before: “An Enticing Expedition Into Nanotechnology’s Potential To End The Energy Crisis”
After: “Energy Industry Flirts With Nanotechnology’s Little-Known Crisis-Ending Capabilities”

Rather than repeating the “en” sound, you can use variation by adding an “ee” (as in “party”) sound to keep the reader guessing until the last word. The first line isn’t too bad and I would refine the second example further; you get the main idea.

4. Be less “awesome”

If you’re new at the skill of headline-writing, see every headline as an opportunity to be concise and descriptive — not to tell jokes or be clever.

Don’t be slick or gimmicky. Accept that someone, somewhere, will whine that practically any interesting headline is “clickbait”. Learn to hear it when you’re slipping into a slick character in order to sound cool or affect unearned expertise.

5. Be less “funny”

Allow humour to shine through the subject matter. Don’t force a “joke” into your headline. On the Internet, no one can hear you laugh as you type. Readers will often miss even the most golden punchline. Better to leave out the funny bits unless they impart valuable information about what your audience is about to read or see.

If the piece itself is funny, your headline will describe the piece and thereby can also (yet not necessarily) be funny. Otherwise, it may be worthwhile to show readers what you thought was fascinating — if you feel that excitement, there’s a chance that the reader will, too.

6. Go away and come back

I just went away to watch Sia perform at the Grammys. When I came back, one of the headline examples begged me to nip and tuck a few words.

Never underestimate the power of distraction in refreshing your brain. Embrace the unexpected, especially if you find yourself obsessively grinding at an idea. Take a break, go away and come back later.

7. Get excited and love your subject.

Even if it’s only for the length of the headline, fall in love with the subject. Act as if it could be the one thing that you woke up to think about all day. Allow it to absorb your attention for as long as it takes to hear the melody and harmony come together in a headline that could possibly bring music to the mind of your reader. Rarely will everyone see the same things you see. The best you can do is give them a chance to find out for themselves. After all, the whole purpose of a headline is to invite the reader to enjoy something you’ve found or created from scratch.

Get excited, get inspired, and write. Your headlines (and mine) will only improve with time.

Maybe even your online dating profiles will improve, too, quickly enough to find a better Valentine in the next 365 days. Or, you might just re-ignite an enticing flirtation with someone you already know; if so, be sure to tell me the story — starting, of course, with a properly tantalizing headline.