I Destroyed 30 Bad Headlines So You Learn to Write Effective Ones

Cover Photo by Thalles Cardoso from Pexels (Adapted)

How to craft headlines people click on

There are only three factors why someone would click on an article: the headlines, the featured image, and the author. Why did you click on this one? Surely something about it attracted you? What is it?

Ever since I became a full-time writer, I’ve been obsessed with headlines. I decided that I’d write 10 headlines every day for practice. Since I started writing online, I wrote over 700 headlines. Most of the earlier ones sucked and led to getting almost no views on my articles. Thankfully, I’m better now.

In this article, I want to help you understand what makes a good headline. And the best way I know is to show you examples of headlines that completely tanked and why they did. Sounds good?

Let’s dive into it!


General lessons from writing and analyzing hundreds of headlines

  • Factual headlines just don’t work.

  • Novelty is key. What makes your headline unique? Could anyone else have written it?

  • Make the purpose of the article very clear in the headline. Will I learn something? Will I be inspired? Will I laugh?

  • Use “you”, not “we”. Readers don’t feel included in “we”.

  • Use subjects people won’t have to Google. Obscure job titles or religious holidays might not attract that many people, for example.

  • Don’t be afraid of longer headlines. Shorter ones tend to be too generic and less creative.

  • Don’t be late to a trend. If you write about a “trend” that’s been going for months, it’s not a trend anymore.

  • Add a credible source when making big claims. If you tell someone they can make millions by reading your article, you better make sure the advice comes from someone who has made millions, not just read about it.

  • Emojis in headlines don’t work. Just don’t use them.


Individual headline analysis

Here are the headlines we’ll analyze:

The 30 unsuccessful headlines we’ll analyze below.

The 30 unsuccessful headlines we’ll analyze below.

1. The Chief Artificial Intelligence Officer

The CAIO of what? This headline gives me no good reason, as the reader, to read further. Why should I care about a person holding that title?

2. Learn The Secret Psychology Of Price

I think the correct spelling would be “pricing” here. This is a little cryptic and generic. There’s likely not a very big audience of readers who regularly set a price on things. Assuming that’s what the article is about.

3. 4 Times When Words Have Misled Marketing Researchers

I’m sure marketing researchers are being misled all the time. Am I going to learn lessons from this? This headline is a little too factual while giving me no reason why I, the reader, should be interested.

4. 8 Powerful Quotes from Comedians To Inspire You

This recipe is a little overdone. New readers might click on it, but older readers have seen that a million times. “Comedians” is a little too broad/vague. “Inspire” rarely is the result readers crave. For the most part, they want to change for the better.

5. Work Efficiently from Home — Even If You Never Meant To

Now that people have been working from home for months, this is a little late. Otherwise, I think the headline is solid, especially with the addition of the second part.

6. Seeking Shelters Outdoors: Celebrating Sukkot this Year

Non-Jews likely don’t know what Sukkot is, cutting a good number of people. The headline isn’t clear as to what the article is about. Maybe it’s about celebrating outside during the pandemic. Is this a how-to? Or a story maybe?

7. I’ve Written and Self-Published 5 Books — Was it Worth it?

I think this would have been better if the result was mentioned in the headline. “Writing and Self-publishing 5 Books Was the Worst Decision of My Life — Learn from my Mistakes”. I haven’t read the article, so I’m not sure that it’s the real story, but people like to learn from other people’s mistakes.

Otherwise, it’s a decent headline.

8. A Simple List of Important Things from a Mom Who Lost It All

I think the biggest issue is that this format is overdone: “Simple -> Big” from “person in distress”. Sadly, Motherhood articles are not that popular on platforms that publish about pretty much any topic.

9. Why Your Company Needs Social Scientists

What’s a social scientist? This is a little generic. According to who?

10. 5 Money Myths that Slow Down Your Financial Progress

Apart from the fact that this format is overly done, it’s a good headline on a topic many want to read about. I’m not sure why this crashed and burned.

11. How Getting Heart Broken Improved My Writing Skills

Everybody’s broken heart improves their writing skills. Also, people don’t want to replicate getting their heart broken, so they can’t put the advice into practice.

12. How to Write a Feature Article That Generates Mind-Blowing Traffic

It’s ironic how this headline tanked. I guess not many people write “feature” articles, or even know what it means. “Mind-blowing traffic” sounds very clickbait.

13. Use The Law of Uniqueness to Find Contentment

This just tells me to use something to get something. Will I learn what the two “somethings” are? Will I learn how to use the first “something” to get to the second one?

14. Personalized Pricing Is No Bogeyman

So what? Also, what does that even mean?

15. Crafting Your Personal Diet for Satisfaction, Fitness, and Wellbeing

As a general rule, using that verb tense in headlines should be avoided. Am I going to learn how to craft a diet? Also “Satisfaction, Fitness, and Wellbeing” are too generic. What’s the concrete change I can expect from crafting a personal diet?

16. Conquer Your Writing Insecurities With an Editing Tool

“An” is too generic. Is it a specific one? Is it an overview of good editing tools? “With” should probably be changed for “Using”.

17. Radical Humility: An Antidote to Donald Trump’s Arrogance and Self-Importance

The headline itself is captivating enough. The only thing is, is there anything I can do about it?

18. If You Want to Land Investors, Stop Obsessing About Your Product

“Landing” an investor sounds a little off to me. It’s also a little generic. What makes this article different? “Investors Don’t Give a C*ap About Your Product, Focus This Instead” It’s a little clickbait, but a lot more effective.

19. 5 Common Mistakes We Make In The Search For “The One”

I’m assuming this is about love relationships? I general, avoid “we”. There’s research proving that readers don’t feel drawn by it. Instead, always use “you”.

20. New Show, Who Dis?

Huh? No clue what this article is about.

21. How an Old Army Vaccine May Have Saved My Life

This is intriguing. The words “may have” make this sound too speculative. I applaud the originality of the first part.

22. ‘Perform’ Your Way Through Life To Transcend the Everyday

This is a lot of keywords to not say much at all. Is this about acting? It’s quite obscure.

23. How To Unlearn Bad Habits

This is generic and overdone. Unless your name is James Clear, people will walk away from this.

24. How to Control Any Meeting and Win Deals, According to a +$1B Investment Banker

It might have been better as a single subject — control any meeting or win deals. I’d go with “win deals”, but it’s quite generic. What kind of deals? Are we talking million-dollar deals or pocket change?

25. How to Be a Full-Time Graduate Student With Chronic Illness and a Part-Time Job

This stipulates you want to be in that situation. I’m guessing the author meant it as: “how to deal with…”?

26. 🎉 It’s here: Our guide to the ultimate self-improvement tool

Looks like this one was just an announcement. In general, announcement headlines tank. Also, doesn’t everyone promise an “ultimate” self-improvement tool? It’s overdone.

27. 6 Powerful Strategies to Breaking Habits without Breaking Down

I think “to” should be “for”. Capital “w” on “Without”. I see what the other did here, but the repetition of the word “breaking” here makes it hard to read for me. “Powerful” seems like the wrong adjective and is too generic.

28. 7 Reasons Why Teaching Is a No-Risk High-Return Personal Investment

What’s the point of the article? Is it to incentivize people to become teachers? Is it meant to uplift teachers? Or is it about teaching more in the sense of passing down your knowledge to others and not so much about the profession?

29. 8 Lessons I Want to Teach My Future Children

Good for your children. What’s in it for me, the reader?

30. The Woman Who Always Wore Two Different Shoes

Unusual? Sure. But why should I care? Factual headlines are too passive and generally don’t work.

Writing good headlines is a skill you can get better at. So far, the best way I know how to improve is to write many daily and get other people’s opinions on them. If you find yourself writing headlines like the ones from this article, you might want to start practicing more.

You can do this!

— Danny