How to turn your good headlines into great ones
Tags: Headlines, Writing, Marketing, Writing Tips, Copywriting

How to turn your good headlines into great ones

Write a ton and find your cheesedoodle Jsanders Follow Apr 28 · 10 min read

Words. They matter. Every single one. Even this one. And this. OK, let’s stop that nonsense and get into it.

No matter what you do for a living, headlines are a vital part of your life. While you may think of headlines as words that copywriters and content strategists write above an article or on a billboard, they actually show up in way more places. I guarantee you’ve written some type of headline. Subject lines for an email to your boss? A clear and clever Instagram caption? A text to Mom reminding her you love her? (Hi, Mom!) We all write headlines every day. Let’s write them better.

Write, write, and write some more

The best advice I ever received in copywriting was simple: Need to write a killer headline? Write 100 of them and choose the best. “100 headlines? That’s crazy,” you say. A bit, but it’s also the best way to reach into every single tiny crevice of your brain and explore all your potential word juice.

An important caveat: Not every project needs 100 headlines. For big projects where you really need to make an impression, I consider it mandatory. For your everyday writing task, like an email subject line, there’s a slightly different approach: Just write more than one. Your first headline usually has a useful nugget in it, but it’s your first thought (which, much like the first pancake of the batch, is never the best). Do yourself a favor and write five more, even if you think you nailed it.

And just so you know I practice what I preach, I wrote 100 headlines for this article. Scroll to the end to see the list.

If you decide to try the 100 headlines exercise, let me share some tips.

Start with first impressions

Before you pull out a trusty notepad (or blank Word doc) and crank out 100 headlines, stop for a moment and let your mind wander. What are your first thoughts after reading a brief? What images come to mind? What words come to you as “power words?” Now start writing.

Writing the first 10 should come relatively easily. When you get to a point where you just can’t anymore, stop. Look out the window. Read an article. Do anything besides trying to write this headline. Then come back, refreshed.

Try a writing prompt

The next 30–40 is where the real meat and potatoes of a brief or insight start to play out. You may find an angle you didn’t see before and riff off that. You may see a word that really stands out from the brief to use as a thought starter. If you’re feeling stuck, try a writing prompt. One of my favorites is taking the first words I hear from a song and using the opening lyrics to start your headline. I’ve had several headlines that didn’t make the cut that started with “It’s been…” (shoutout to all the BNL fans out there).

Also, the internet can be a wonderful resource to give you a jumping-off point. I recommend trying different writing prompts to see what works for you. The Reddit group r/WritingPrompts is excellent.

Let the bad headlines flow

When you reach headline #50, you should have some good ones and a few not-so-good ones. And that’s part of the process! If a terrible headline crosses your brain, write it down. Once it’s on paper, it’s out of your head, never to exist again.

Keep your toolbox handy

Writing takes practice — and lots of it. Some days you’re on, and it flows from your fingertips like a raging waterfall; other days, it’s like you’re squeezing the juice out of a week-old lime. What helps me on those not-so-juicy days is my personal toolbox — a set of writer-y tools to use when writing isn’t coming as naturally as I’d like it to. Every writer’s toolbox is different.

One of my favorite tools is the five-minute writing warm-up. Before I jump into my assignment, I free write for five minutes straight. There’s a great tool called “The most dangerous writing app” that forces you to keep writing for a predetermined amount of time, or your work disappears. I would never use this for something essential — but as a way for me to force myself to write for five minutes, it sure does the trick.

Find your magic hour

As you slog through headlines 70–80, try to come with fresh eyes. If the timeline is flexible, pick it up during your “magic hour” — a.k.a. the time of day when you do your most productive writing. Mine is 9–11 am, which is why I’m slow to respond to Slacks and emails in the morning.

Try 8 different styles of headlines

Getting to 100 headlines takes some serious brainpower. And sometimes you need some help. These headline styles are useful as jumping-off points if you’re trying to squeeze out just a few more lines.

Questions

Instead of writing a statement, write your thoughts as a question. It’s like Jeopardy, except your headlines win.

e.g., Could your savings account be doing more?

2. Twisting a cliché

This is a dangerous one. Cliches exist for a reason. Sometimes a great headline can come out of it. Other times they seem forced, silly, or irrelevant. But this still can be a useful category to play around in.

e.g., More money for you. Fewer problems for your accounts.

3. Directive

Include a strong action at the start of your headline. These work well when you need a clear call to action.

e.g., Take a look at our rates. What you find may surprise you.

4. Curiosity

Everyone loves a mystery! This style piques interest by asking something your audience may not have thought of yet.

e.g., Wondering if you can afford a three-bedroom in the city? Check our mortgage calculator first.

5. Label/Brand name

This one works by playing with words or feelings associated with the brand. For NerdWallet, this is where our nerdy passion comes into play.

e.g., For all your money questions, Turn to the Nerds.

6. Comparison

While we never want to trash our competition, you can hint at things we do differently. You can also compare yourself to a general category, not necessarily a competitor brand.

e.g., Stop reading the fine print. Let us find the best of the best for you.

7. How to:

Another super simple template. Just start your line with “how to.” It may not make it into your final line, but it helps by giving structure.

e.g., How to find a better mortgage than your brother-in-law.

8. Listicle

This is a way overdone technique, but it’s useful as a thought starter.

e.g., V1: Reason #24 to use NerdWallet: Your credit card could use some new friends.

V2: Your credit card could use some new friends.

Take the best ones and make them great

Once you have your long list, the real work starts. Go through each one, highlight your favorites, and organize them into buckets or themes. Color-code them. Choose your ten favorites and edit, edit, and edit some more. Even if a headline is excellent, it’s worth your time to see if you can make it better. Do you need that word? Are you writing into a cliche? Is that even a joke? Editing your top ten turns a good headline into a great headline.

Find your cheesedoodle

This is one of my favorite headlines of all time. Not only does it do the “twisting a cliche” thing very well, but it also uses the power of word choice to make it memorable. This line would work fine if it ended in “orange slices’’ or “juice boxes,” but it really shines with an even better word choice. Always try to find words to plus up your headline. Always try to find your cheesedoodle.

So…what’s a good headline anyways?

But how do you identify what’s a good headline and what’s a bad headline? Writing is so subjective and there is no clear-cut blueprint that helps you craft the perfect headline. For me, I know in my gut when a headline just feels right. It makes me smile, inspires something, and makes me feel like there is some good in the world. And, of course, it ladders back to the brief. The best way to identify a good headline is to practice writing a bunch, looking at others for inspiration, and always use your brief as your guide.

Writing great (or even good) headlines doesn’t happen overnight, even when deadlines demand it does. The best work always comes after rounds of revision and a lot of discarded, failed attempts. But every day you put pen to paper (or keystroke to Word doc), you improve. The best way to be a better writer is writing (and reading!) every day — whether for fun, for work, or just shooting a text to Mom. So keep writing and always remember your cheesedoodle.