How to Write a Killer Headline

A headline as real as if we were there. Source:

Did my headline get you interested? I sincerely hope so, otherwise, I could not fulfill the promise. Although rules should always be broken, it is good to know them to begin with. For this article, I have looked for people smarter than me who could explain what I did for 15 years with more or less accurate intuition. Most reflection comes from advertising buffs but when it comes to headlines, their word is good for all writing. Here are a few simple ideas to get your headline right.

“Unless your headline sells your product, you have wasted 90 percent of your money.“

— David Ogilvy

That quote is in stark contrast with the following:

“Your headline has only one job — to stop your prospect and compel him to read the second sentence of your ad.”

— Eugene Schwartz

But both are right and point out the importance of that one line. This article is published on Medium behind the paywall. Its goal is to make you click and open the page of the article. If you are a member than the headline and your action will bring the author a few cents. Of course, the body copy has to fulfill the promise of the title, otherwise, it does not sell. In the case of Medium, the author is paid in applause and a following.

Rule No 1: the headline is a promise that is honored by the body copy

You would click that, wouldn’t you? Source:

The whole nine yards with headlines

Emanuel Haldeman-Julius published a series called Little Blue Book in the first half of the previous century. He published classical literature in an affordable fashion for poor people. He advertised his books with sensational claims such as “At last! Books are cheaper than hamburgers!” He not only is a pioneer in guerilla marketing, but he also wrote a book on how to sell mail-order books. The following table shows titles of books he sold. When he wasn’t satisfied with the sales he rewrote the book titles with great success:

Mind you, these were all classical novels by well-known authors, including Molière. While I would not advise changing “Crime and Punishment” into “Gelato and Cigarettes” it shows us the power of thinking about headlines. Haldeman-Julius in his booklet ‘The First 100 Million”:

“A similar poetic mistake was made when several volumes of Jack London’s stories were put into the series. One book, because I fancied the phrase from one of the stories, was called Tales of the White Silence. This seemed to me particularly expressive. I really thought the book would go. Of course, the name of Jack London carried the book satisfactorily, but still, it seemed to me that it should do better. At last, I was forced to give up my fanciful preference for the “white silence,” and now I think that the newer title is really the better. It is: “Tales of the Big Snow”. The difference in expressiveness is instantly apparent.”

Who’s your clickbaiter now? Source: twitter: @edyong209

What sells is a desire. Finding that is science

Advertising author Drew Eric Whitman pointed out, how the basic human desires resonate in titles.

  1. Survival, enjoyment of life, life extension.
  2. Enjoyment of food and beverages.
  3. Freedom from fear, pain, and danger.
  4. Sexual companionship.
  5. Comfortable living conditions.
  6. To be superior, winning, keeping up with the Joneses.
  7. Care and protection of loved ones.
  8. Social approval.

“What art should mean” helps you with Social approval (8.). “Quest for a Blonde Mistress” clearly promised to fulfill a sexual desire. “How to Argue logically” helps you to be superior. “Casanova” is sexual again while “Truth About the Riddle of Life” follows the most basic desire about survival and life. I would put the headline for this article on category 6 — to be superior and winning.

Rule No 2: address basic human desire in your headline

That’s how that economy works. Source: thoughtcatalog

Think of your audience when writing the headline

Ad-man Bruce Barton said: “How can the headline be changed to be more interesting or appeal to more people?” Countless articles have been written about target group segmentation. When it comes to headlines, let’s focus on examples. Here Barton on selling a correspondence-school advertisement:

“The old headline was ‘John Smith made $110,000 the first year writing motion picture scenarios.’ The new headline was ‘John Smith sold his first motion picture scenario for $9,000 one month after completing this Course.’ The advertisement with the new headline drew enormously, and the explanation is, of course, easy. Every reader could imagine himself or herself making $9,000 but few could imagine themselves making $110,000.”

An example by John Caples, another smart ad-man, shows us what a headline is all about: engaging the reader.

Old headline: “Are You Afraid of Making Mistakes in English?”

New headline: “Do You Make These Mistakes in English?”

There is always a response to something people read. What are the responses here? With the old headline, the response might be “yes”. With the new headline, the response is: “which mistakes?” — giving us the promise that we find interesting blunders in the body copy. The engagement is stronger.

Caples follows with this example: “The final headline was ‘HOW A FOOL STUNT MADE ME A STAR SALESMAN’. The copywriter could have written the headline as ‘HOW I DID A FOOL STUNT.’ This is a good curiosity headline that could have attracted some readers. The copywriter could also have written ‘HOW I BECAME A STAR SALESMAN.’ This is a good self-interest headline and would have captured many prospects. But combining the two features, curiosity and self-interest in a single headline…” did the trick.

Rule No 3: Write different headlines. Play through the potential responses and choose the headline with the strongest intention to continue reading.

Question is if he won the case? Source: Thoughtcatalog

Words make the headline — start with the right one

John Caples has not only condensed desire into just four qualities, but he also gave us words that are good to have in a headline.

“There are four important qualities that a good headline may possess. They are 1. Self-interest. 2. News. 3. Curiosity. 4. Quick, easy way.”

— John Caples

Caples’ words:

  1. FREE
  2. NEW
  3. AT LAST
  4. THIS
  8. NOW
  9. HERE’S
  10. THESE
  11. WHICH OF
  13. LOOK
  16. HOW
  18. DO YOU
  20. CAN YOU
  21. IF YOU

Haldeman-Julius, the Little Blue Book-guy again. “There has always been a market for books which make things plain, such as Evolution Made Plain. Then I tried ‘introductions’ to this and that, and scientific subjects ‘for beginners,’ but neither of these variations of title has been quite so successful as ‘the facts you should know’ caption. An important secret of successful titling is to be imperative, to insist on the very name of the book that the reader should have it!“

It is not without irony that Haldeman-Julius’ book “The First 100 Million” was recently republished with a title change. “First 100 Million — How To Sky Rocket Your book Sales With Slam Dunk Titles”. Ain’t that neat? And yes, he sold 100 Million copies of 1.200 different books in nine years in the 1920ies.

Shit happens. Source: thoughtcatalog


I started with Drew Eric Whitman — CA$HVERTISING — How to Use 100 Secrets of Ad-Agency Psychology to Make Big Money Selling Anything to Anyone. Now that is a title! He boils down the great ad-people of the past into simple recipes. I then looked at his sources:

Eugene Schwartz — Breakthrough Advertising. First published in 1966, reprinted in 2004. This is the masterpiece. And oddly up-to-date. The internet has not changed how people respond to headlines and body copy. Clickbait is as old a technique as advertising itself. It is very likely that you can’t get the original book, but there is a ripoff explaining his stuff.

Emanuel Haldeman-Julius — The First 100 Million. That’s an oddity, over 90 years old. It’s a study on publishing 1.200 books in nine years and what makes them sell. This might be especially interesting to book writers looking for the perfect title.

John Caples — Tested Advertising Methods. Reprinted countless times, a book with many examples and an exhaustive amount of tips. If you can’t write good headlines afterward, you can’t be helped.

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +392,714 people.

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