Behavioral Science

Upworthy Creates 25 Headlines per Article. Should You? — Upworthy’s Adam Mordecai Explains.

by . October 7th, 2014

Few things on social media are as divisive as shares from Upworthy, a media sharing group. To drive the point home about how huge they were, check out this graph:



For over a year, its curated content dominated Facebook and other social media platforms, causing Facebook to take steps targeting sites in broadly the same category as Upworthy to take them down several notches.

upworthy crash


While no longer as successful -at least in relative terms – as it was, all entreps and marketers can learn a thing or two from Upworthy.

What’s amazing is that Upworthy (and BuzzFeed) managed their social media feats not through the development of technology – or even content.

What did matter was how the content would be consumed by users.

In a recent Quora post a couple of months back, Adam Mordecai mentioned that he writes 25 headlines for every single post. If you think about it, it seems like an insane number of headlines. Many occasional writers can take hours to come up with one headline that satisfies them, but Adam claims to be able to write 25 in 15 minutes.

 How do they test the headlines?

While Adam doesn’t explain the specifics, the other things he does says give us plenty of food for thought.

Here’s Adam Mordecai’s answer in verbatim:

We have a custom click testing system that I call the magic unicorn box which we built internally. I can’t say how it works. All I can say is that I put my headlines in the box, and the magical scores come out, and then I make decisions based on that.

The reason we write 25 headlines is that it’s an old strategy from my boss’s old gig, The Onion. At the Onion, they would “crap out 25 headlines” as fast as possible. Then in the pitch room, they’d assume that 20 were crap, and the remaining 5 had an opportunity to be an article. Then once they had their headline, they’d finish their piece.

The reason it’s always 25, no less, is that it forces you to think waaaay outside the box when writing. You get desperate around headline 21, and do something so out of left field that it’s not the typical headline. The key is to not overthink your headlines and make every sentence perfect. Remember 20 will be crap. So just get them all out.

As for patterns to my headline writing, there isn’t really a distinct one. The following tips are for people who want to reach the widest audience possible. This can dilute the strength of your voice, so you have to work twice as hard not to sound bland, but if you care about a wide audience it works pretty well. The main structural rules for headlines in my mind are as follows:

1.) Tell a story in your headline, but don’t give it all away.

(This is what makes us so successful, though some people really hate it.)

2.) Give away as much as humanly possible.

The more transparent you can be with the subject matter the better.

3.) If you’ve got some heroes and villains…

…play them off each other.

4.) To optimize shareability you want to make sure everyone can feel comfortable sharing it.

Think to yourself, “Would my mom share this headline?” If not, do something different. Unless you are only targeting a subgroup and don’t care about shareability.

5.) Don’t depress people so much that they want to give up on humanity.

Negative headlines breeds negative shares.

6.) Don’t curse in your headlines.

Moms hate it (and are the biggest sharers on the internet by a significant margin. Mothers With Children Under 5 Most Active on Social Media [STUDY]

7.) Don’t make people take positions they might be uncomfortable with.

For example, “I Really Hate All White People” is going to not get shared, whereas, “An Open Letter To Pasty People” is far less hostile and more likely to get shared.

8.) Don’t use terms that overwhelm, polarize or bore people.

I never use Social Security, The Environment, Immigration, Democrats, Republicans, Medicare, Racist, Bigot, etc… You can talk about issues without giving away what they are. Most people aren’t going to want to look at a Immigration video. Once they get to your site and hit play, they may reconsider. (Though immigration is particularly challenging. )

9.) Don’t be shrill and judgy, let the facts speak for themselves.

Anytime I’ve made that mistake, the content dies a horrible death. As an example, when Todd Akin came out with the cartoonishly awful idea that women’s bodies stop them from getting pregnant from rape, I started with the headline, “Meet Todd Akin. He’s A Horrible Human Being. Share This So Everyone Knows.” No one clicked or shared.

When I changed it to “A Congressman On A Science Committee Doesn’t Understand How Science Works” it did waaaay better with people across the political spectrum. Because people didn’t have to be afraid of sounding partisan.

10.) Don’t oversell.

We’ve worked hard to tone ourselves down, as occasionally our headlines would veer towards THE BIGGEST THING EVER, when it was actually THE PRETTY INTERESTING BUT NOT BIGGEST THING EVER. It’s not worth dragging people to your site if they feel ripped off after they get there.

11.) Don’t be afraid to talk like a human.

People like human conversation.

12.) Don’t make obscure pop culture references.

90% of the American audience has never seen half the shows you are referencing. Instead of Jennifer Lawrence Talks About What It’s Like To Be Judged, it’s “That Lady From The Hunger Games” Nobody knows who your favorite character is played by.

13.) Always test.

No matter how clever you think your headline is.

14.) Speaking of which, don’t be too clever.

People won’t get it and they won’t click and then you lose.

15.) Have fun.

Dry headlines bore people.

16.) Always write 25 headlines.

Or the terrorists will win.

BONUS UPDATE: Try descriptive headlines.

We’ve found that they usually can tie vague ones. There’s nothing I love more than giving it all away.


Again, these rules are for getting the widest audience possible. If you have a targeted audience that might not like these rules, then don’t ruin their experience by being like us. Our voice is not for everyone.

Also, just FYI, I’ve broken every single rule on this list at some point. I learned by experimenting and failing. So test on your audience, have fun with it, assume you will make mistakes, and win the Interwebs.

And write 25 headlines. (I can do it in 15 minutes now that I’ve practiced enough.)

An important factor that I seemingly left out it that your content should not ever be like this. Your content should challenge people, make them think, and be more than just clickbait. However your Headlines will be more effective with these rules.

Voiceiness in your content is actually really important. People refrain from sharing headlines and images that make them uncomfortable. However they will share content that does. As long as they won’t be judged for the packaging on Facebook.

So make your content safe for Facebook to share, but live on the edge with the content you present on the other side of the click.

Source: -What tools does Upworthy employ to test its headlines

More: Why You Should Be More Like BuzzFeed
Things entreps should take away from this:

1.) Adam Mordecai’s ideas apply to nearly everything you sell.

Whether you’re selling a new app that does freelancer’s taxes or a batch of your special cinnamon-pumpkin cupcakes, several things remain true. We all want to feed good, we don’t want to feel stupid, and we act based on out emotions. How you sell any product or idea hinges on these things.

2.) You are not Upworthy.

Though Adam didn’t say it outright, you probably don’t want to appeal to the lowest common denominator. The tactics employed by all those social media outlets clogging up your feed may not work for you if you copy them outright. I’ll do you one better and guarantee that copying their systems will never work for you.

Each and every marketer and entrepreneur need to find their own voice (or set of voices) through trial and error.

3.) Perceived quality might suffer if more people have access.

Over-saturating your market with promotions can cause people to care less about what you’ve got. Plus it gets annoying pretty fast – unless you switch things up a little.

4.) We don’t like being emotionally manipulated.

This is one of the main reasons Upworthy and Buzzfeed are often reviled.

5.) That said, we sometimes can’t help but BE led on.

On the other hand, the success those social media outlets had with those tactics speaks for itself.

6.) Act based on how your audience will respond.

Anything you try to sell should be about benefits not features. Upworthy nearly always tries to promise or inspire, implicitly (heck their name does that already) or explicitly on their titles.

7.) Try to make your audience feel good.

If you can make them feel optimistic, clever, cool, or altruistic by virtue of them just sharing something you’ve

8.) You won’t ever get it right all the time.

The “25 headlines” per post process just begins to touch on many of the things you will need to do in order to succeed at anything. Most of us will have to fail a bunch of times before we succeed.

9.) Originality is overrated.

Case in point: Apple. Few of their products in the past 15 years were particularly groundbreaking or original from a technology point of view. Apple continues to be a huge deal because:

10.) The human factor is underrated.

Like Upworthy, Apple considers how their market would react, and they work their way back from there. Forgive this oversimplification, but you just have to see how things that were “ahead of their time” failed. In most cases, the creators put the features ahead of the benefits, and the technological limitations ahead of the humans who would need their products.


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Arthur Piccio manages YouTheEntrepreneur and has managed content for major players in the online printing industry. He was previously BizSugar's contributor of the week. His work has appeared multiple times on The New York Times' You're the Boss Small Business Blog. He enjoys guitar maintenance and reading up on history and psychology in his spare time.