How to turn your good headlines into great ones

Write a ton and find your cheesedoodle

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.

  1. 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.

As promised, here are the 100 headlines I wrote for this article:

  1. How to write headlines that don’t suck
  2. How to write better headlines
  3. Looking to get attention? Write better headlines.
  4. Ready to make an impact? Start with better headlines.
  5. Headlines matter!
  6. Words matter and headlines tell a story
  7. Why your headlines aren’t working
  8. Headlines and how to write them better.
  9. Are you reading this? How to write better headlines.
  10. Headlines. The who, what, and how of getting great ones.
  11. How to turn your good headlines into great ones
  12. Short and sweet: How to write great headlines
  13. Write better headlines now
  14. Ready to write better headlines?
  15. Words matter: How to write better headlines
  16. How to use the right words to write better headlines
  17. Why headlines are so important
  18. Love writing? Here’s how to be even better.
  19. Everyone writes. How to write even better headlines.
  20. Your headlines. Your voice.
  21. A headline by any other length wouldn’t be as good
  22. Ready to write better headlines?
  23. Write, write, and write some more: Your guide to better headline writing
  24. A guide to writing better headlines
  25. Tips and tricks to write better headlines
  26. Your headlines suck. Here’s how to make them better.
  27. Turn good headlines into great ones.
  28. Just one more. Tips for writing better headlines.
  29. Headlines matter.
  30. Writing better headlines starts with 100
  31. 100 ways to write better headlines
  32. Need better headlines? Keep writing.
  33. How cheesedoodles can help you write better headlines
  34. Your toolkit: Headline writing
  35. A writer’s toolkit: Write better headlines
  36. The secret to better headlines? Time, patience and a lot of words.
  37. Headlines: The secret to being short and sweet
  38. Headlines matter. Good ones make a difference.
  39. What a good headline can do for your project
  40. How to write good headlines, and how to make them even better
  41. Great headlines start with good ones
  42. Write, revise, and sleep on it: The secret to good headlines
  43. How a great headline can turn heads
  44. Why writing more than one headline is important
  45. The 100 headline challenge
  46. The key to writing good headlines? Write a ton of them.
  47. If you want to be a great headline writer, write 100
  48. Writing headlines doesn’t stop in round 1
  49. Is this a good headline? How to ensure your headlines are effective.
  50. Writing effective headlines that get clicks
  51. Marketing headlines: A toolkit.
  52. A writer’s toolkit: Killer headlines.
  53. How to write killer headlines
  54. Want to write better headlines? Start by writing 99 bad ones.
  55. Headlines—or, the pursuit of words that matter
  56. How to tell if you wrote a great headline
  57. The difference between good and great headlines? 99 bad ones.
  58. Why writing more than one headline works so well
  59. Open up your mind and write more headlines
  60. Write headlines. Then write some more. Then choose.
  61. Why it’s so important to write more than one headline
  62. The writing process: Headlines and the most important words
  63. Grab attention with these headline writing tips
  64. The secret to writing good headlines is writing a lot of bad ones
  65. Need a good headline? Write a bunch of bad ones first.
  66. Good headlines are birthed from the bad
  67. Why the 100 headline challenge will make you a better writer
  68. Looking for better headlines? Take the 100 headline challenge.
  69. You’re almost there. The key to better headlines.
  70. Cheesedoodles: The secret to better headlines
  71. How a cheesedoodle can make you write better headlines
  72. Looking for better headlines? Find your cheesedoodle.
  73. How a cheesedoodle made me a better headline writer
  74. Sifting through the garbage: How to find a great headline.
  75. Everyone can write better headlines
  76. Why writing more than one headline will help your career
  77. How writing headlines can unlock your true writing potential
  78. Need a headline? Start by writing 100.
  79. Your headlines can get better with this one weird trick
  80. One weird trick to get better headlines
  81. How writing more headlines can unlock your true potential
  82. Everyone writes headlines. Let’s write better ones.
  83. Just one more: How writing more headlines makes them better
  84. The secret to a great headline? Write a bunch of them.
  85. The best writing advice I ever got? Write 100 headlines to get one good one.
  86. How writing 100 headlines helps you get 1 great one
  87. The key to a great headline lies in writing a bunch
  88. Why you should always write more than one headline
  89. Your headlines aren’t bad, you’re just not writing enough
  90. The search for the perfect headline
  91. Write the junk out: How to find the perfect headline
  92. The writer’s toolkit: 100 headlines
  93. What’s in your writer’s toolkit?
  94. Writing better starts with identifying your writer’s toolkit
  95. How to write better headlines? Practice, practice, practice.
  96. Headlines and the search for the elusive headline
  97. Your writing isn’t bad, you’re just not writing enough
  98. 100 ways to write the perfect headline
  99. 100 tips on writing better headlines
  100. Looking to write better headlines? Here’s 100 ways to get there.

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