Write twenty headlines, keep one: my plain-text headline routine

For a long time the headline was the first thing I wrote and the last thing I thought about. I'd type something at the top of a blank file so it had a name, write the whole piece underneath, and publish with that placeholder barely changed. Then I'd wonder why a piece I was happy with got so few clicks.

These days I write headlines last, and I write a lot of them. The whole routine lives in one plain text file and takes about fifteen minutes.

Finish the draft first

A headline is a promise about what the article delivers, and before the draft exists I don't know what that is. Pieces drift while I write them. A planned list of tips turns into one longer argument, or the best part ends up being an example I never planned.

So the working title stays rough on purpose. Once the draft is done, I read it once and write down, in one plain sentence, what a reader gets out of it. That sentence is not a headline, but every headline I write afterwards has to keep its promise.

Twenty lines in one file

Next to the draft I create headlines.txt and fill it with candidates, one per line. I aim for about twenty. The first five are usually obvious, and the useful ones tend to show up once the obvious ones are out of the way.

To keep from writing the same line twenty times, I rotate through a few shapes:

• A plain statement of what the piece does
• A question the reader might actually type into a search box
• The result, without the method
• The method, without the result
• A version aimed at one specific reader

For this article, a few of mine looked like this:

How I draft headlines
Write twenty headlines, keep one
Why your headline is the last thing you should write
A plain-text routine for drafting headlines that say what the article is about
Headlines: a short guide

None of them is finished. They are raw material.

Sort them by length

Headlines get cut off in search results, in feeds and on narrow phone screens. I use roughly 60 characters as my own upper limit. It's a rule of thumb, not a hard line, but it stops me from writing a whole sentence and calling it a headline.

Counting by eye is hopeless, so I let awk do it. This prints every line with its length in front and sorts the list from shortest to longest:

awk '{ print length($0), $0 }' headlines.txt | sort -n

For the list above, the output starts like this:

21 How I draft headlines
24 Headlines: a short guide
32 Write twenty headlines, keep one
52 Why your headline is the last thing you should write
78 A plain-text routine for drafting headlines that say what the article is about

And this shows only the ones over the limit, with their line numbers, so I know which ones to shorten:

awk 'length($0) > 60 { print NR ": " $0 }' headlines.txt

Some versions of awk count bytes rather than characters, so accented letters can make a line look slightly longer. For a rough limit, that's fine.

Cut the ones that hide the topic

With the list sorted, I go through it and delete lines. A candidate goes if:

• It's clever but someone skimming wouldn't know what the article is about
• The important words come at the end, where they might get cut off
• It promises more than the draft delivers
• It could sit on top of a hundred other articles

"Headlines: a short guide" fails the last test. It's not wrong, it's just interchangeable. The 78-character line says the right things but needs trimming, and trimming it is often how I find the final version.

Test the survivors against the first paragraph

Usually three or four lines are left. I read each one, then my opening paragraph straight after it, the way a reader would after clicking. If the opening doesn't pick up the promise within a sentence or two, either the headline or the opening has to change. Sometimes it's the opening, which is a nice bonus.

Keep the file

I don't delete headlines.txt when the piece goes out. The rejected lines are often good subheadings, newsletter subject lines or the opening of a short social post. And when I go back months later to update an article, the list reminds me which angles I already tried.

My headlines are less of an afterthought now. They're a short writing job of their own, done when I finally know what I'm promising.