This Boring Task Has Made Me A More Creative Writer

Can doing the same thing over and over actually make you more creative?

The idea of that—at first —seems mundane. Quite the opposite of creative. But, a few months ago, I made one little change to my normal writing routine—a change that required me to repeat the same task many times—that has left me feeling more creative than ever.

Back in December, we launched the new design of Riskology.co. Around the same time, I started updating the style of content I write here. I was proud of the articles and wanted to make sure as many people as possible read them.

So, I changed one habit in my writing routine I thought would help that goal. Instead of working for hours and hours on an article—thoroughly researching, writing, editing, re-writing and publishing—to come up with just one title, slap it on the top of the piece and call it a day, I forced myself to write 20 different options.

It was a conversation with my friend, James, that turned me onto this. He told me a story about how he’d learned writers for Upworthy were required to write 20 different headlines before they were allowed to publish a new piece.

At first, it seemed crazy. A title is a title, right? What is writing 20 of them going to do? Seems kind of boring, actually. But if it works for Upworthy (and it really works for them), I thought I ought to give it a try.

Here’s what I learned: The way I’ve written titles for the last four years has been very uncreative.

When I started forcing myself to wait until I had 20 options in front of me before publishing an article, I noticed I’d get stuck around number ten. I’d have an idea of what I wanted the title to be, write it down, and then make minor adjustments to it nine more times.

I’d look at the page and see ten headlines that were basically the same. But there were still ten more to write! What do I do?

This is where the magic of forcing myself to come up with ten more headlines kicks in. Since I’m out of minor tweaks after ten rounds, the only option is to head an entirely different direction. I have to throw out the idea of small changes and start making really big ones.

Here are the 20 headlines I wrote for this post:

1. Can Repetition Make You More Creative?
2. Can Doing The Same Thing Over And Over Make You More Creative?
3. Can Repetition Actually Spark More Creativity?
4. Can Mundane Repetition Spark More Creativity?
5. Can Mundane Repetition Actually Make You More Creative?
6. Can Mundane Repetition Actually Spark More Creativity?
7. I Started Using This Lesson From Upworthy, And It Made Me More Creative (No, Really)
8. This Lesson I Learned From Upworthy Changed My Life. Not Really, But It Made Me A Better Writer
9. This Lesson From Upworthy Changed My Life. Just Kidding. It Made Me A Better Writer, Though
10. One Lesson About Creativity Only Upworthy Knows
11. How Could Repetition Make You A More Creative Person?
12. This Is The Only Useful Thing I’ve Learned From Upworthy
13. Upworthy Sucks, But I Did Learn This Neat Trick About Creativity From Them
14. The Truth About The Mundane And How It Makes You More Creative
15. There’s Nothing Like Mundane Repetition To Make You A More Creative Person
16. Nothin’ Like Mundane Repetition To Make You More Creative
17. One Incredibly Mundane Task That’s Made Me Much More Creative
18. This Boring Task Has Made Me A More Creative Writer
19. Can Creativity Come From The Completely Mundane?
20. This Is The 20th Headline I’ve Written For This. I Hope You Like It

After writing 20 headlines, I usually find there are only about three or four different themes with variations of each. But those three variations are completely different. And, perhaps unsurprisingly, the ones that come out towards the end have almost always ended up being the titles I choose because they’re more interesting. By this point, I’ve given up on repeating the same thing, and forced myself to move to different ideas.

I kept track of which iteration I chose for a month and found every single title was one that came out after at least 14 tries.

And the results have spoken for themselves. You all have read the articles here more than ever. I hope you’ve enjoyed the more creative titles!

The lesson, here, is simple. If there’s something you want to be good at, don’t rest after just a few tries. Even if the thing you’re working on is just one small piece of the puzzle.

Force yourself to deconstruct your work and start over many, many times. Do what I did. Make a rule for yourself that you won’t consider your work finished until you’ve done it 20 different ways.

Soon, you’ll find yourself coming to answers—creative answers—you might never have thought of before.