The Secrets Of Writing Smart, Long-form Articles That Go Absolutely Viral

Going deep with the founders of Wait But Why, who show that thoughtful, long-form content is king.

The Secrets Of Writing Smart, Long-form Articles That Go Absolutely Viral
Image credit: Tim Urban, Wait But Why

Note: BuzzFeed publishes several long and excellent feature stories every week, as you can see on their Big Stories page. We did not intend to belittle the work of the editors and writers there, and we regret if that was the takeaway. — Noah Robischon, Executive Editor.


Over the last several years many professional writers and journalists have lamented what’s been called the BuzzFeedification of the Internet.

This is an Internet where, it seems, a steady stream of churn-and-burn content is king, and anything of substance is only second best. It’s an Internet where if you want to get a job writing for one of the hottest media companies on the web, your knowledge of how and why information is shared online is as important as your writing talent. And it’s an Internet that the content masters at sites like BuzzFeed, PlayBuzz, ViralNova, and Upworthy have created in direct response to the supposed needs of the TL;DR Generation–a generation comprised of modern Internet users conditioned to communicating with text messages, 140 character tweets–and, when even that’s too much, posting a Snapchat pic that exists for less time than a yawn.

Increasingly, news organizations are relying on apps like Snapchat and Facebook not only to build their audiences but to host their content, in ways that are designed to capture readers’ supposedly shrinking attention spans, which are thought to be so short that anything longer than a six-second Vine or a listicle that takes longer than 30 seconds to assimilate could have them clicking or tapping away to the next bit of stimulation.


“Long-form writing is great,” an editor at one of these major new-media publications once told me, “but no one shares it.” I protested, and he challenged me to send him a link to one long-form site whose articles get at least tens of thousands of shares. “Not just one article–a majority of the articles on the site.”

At the time, I couldn’t. But now I have a link for him: A young, bare-bones website called Wait But Why is disproving the notion that thoughtful, long-form content and virality are mutually exclusive.

The Internet Gave Up On People

“In 2013, when we were discussing this new project, we noticed that it seemed like the most popular writing these days was stock photos and lists that were really crappy and short–-and sometimes really clever and great–-but really short. It was like the Internet had given up on people having attention spans,” says Tim Urban, the thirtysomething writer and cofounder of Wait But Why, the sometimes humorous, almost always profound, long-form explainer site whose articles have captivated millions and garnered influential fans, including Elon Musk and Sam Harris).


“But we didn’t really buy that,” Urban says. The site’s first post was called “7 Ways To Be Insufferable On Facebook“–“a classic BuzzFeed headline.” The story itself was not classic BuzzFeed: across a breezy but smart 3,000 words, the article dug deep into the psychology of social media. Urban and his co-founder, Andrew Finn, figured that even if nine out of 10 people read the first few paragraphs and left, that 10th person would be enough to begin building a loyal following.

“We took a bet that long but really thorough, really high-quality articles would not only be acceptable to certain people but would be a really fresh, standout thing in a current world of really short list articles. And that smart people would start reading it, and would keep reading it and get to the end. Then they’d want to share it, even more than if it were a great short article.”

Just 19 months after the site began, that bet has paid off in spades. Along with influential readers like Musk and Harris, Wait But Why now has numbers any other startup blog would be envious of: A total of 31 million unique visitors and 87 million page views, with monthly averages of 1.6 million uniques and 4.6 million page views, according to Urban. Its newsletter has over 106,000 subscribers. The site is now visited by people from every country in the world every month, and its content is so viral its readers offer to translate it into other languages, including Chinese, so their non-English-speaking friends can read it.


And this has happened, the site’s founders say, organically, without buying any followers or likes, or even pressing hard on social media.

This is all the more impressive considering there just isn’t a lot of content on Wait But Why. Unlike viral churn-and-burn content sites, which posts dozens of articles a day, Wait But Why has only published just over 80 articles in total. That’s an average of just one a week; 63 of them are pieces that stretch to over 2,000 words, with some reaching more than 3,000. The site’s slow schedule, which began as one post a week, is now more erratic. “After a post goes up, the next one might go up two days later or three weeks later,” Urban says.

Common Internet logic would say that articles of those lengths just don’t go viral, and that an editorial website that only publishes occasionally certainly has no chance of retaining readers. But the success of Wait But Why has flatly disproved that. Its most viral article, a 1,600-word essay explaining the psychosocial reasons why Generation Y is so unhappy, has well over 2 million shares. The site’s other long-form essays typically get in the range of 300,000 to 600,000 shares each. Even the lowest performing articles boast share numbers in the mid-five-figures.


In eschewing churn in favor of substance and breadth for depth, Wait But Why’s essays also capture a level of reader engagement that even the new-media giants would be envious of. Wait But Why’s audience (“From all over the world, all different ages, all different backgrounds,” says Urban) doesn’t just share stories; They stick around the site to discuss articles in the comments, which can number in the thousands and, in some cases, are almost as long and thoughtful as the articles themselves.

What Really Drives Sharing

With the quality of Wait But Why’s articles, their massive reader engagement, and their ability to consistently go viral, you’d think that the site proving long-form can be good business would have a team of writers and cutting-edge social media experts behind it. In fact, it’s just run from the laptops of two friends separated by the span of America between them.

Wait But Why’s only resident writer, Tim Urban, lives in New York. The site’s other cofounder and the man who’s responsible for the business side of things, Andrew Finn, lives in Los Angeles. Urban has a BA in Government from Harvard and Finn earned his BBA from the University of Michigan, but in describing Wait But Why‘s ascendence, neither cites their degrees or experience running their other companies, two ed-tech startups they previously founded called ArborBridge and truePrep. Instead they credit the site’s success to their friendship since kindergarten and the decades of esoteric conversations only best friends can have.


“We’re both really curious people who like to really think through all the angles of things,” says Finn. “Ever since we were young, we’ve really tried to come up with an original, bottom-up view of things, not necessarily the one that just got handed down from parents or society or whatever the norms are. We’ve really always tried to challenge that.”

And it’s those thoughts and conversations, they say, that would eventually become the foundation for many of Wait But Why’s long-form, viral essays.

“When we come up with a topic we want to talk about, it’s not something we’re talking about for the first time,” says Finn. “It’s something we’ve probably talked about for 50 or 100 hours. Then it’s probably more of a question of ‘How do we build a good post about that?’ and then ‘How does Tim write it and flesh out those ideas?’ Because if you can, in an article, really articulate something that people think but just has never been articulated in such a compelling, engaging, interesting way, that’s something that they really get excited about and want to share.”


And, he adds, “if you can blow someone’s mind–really, genuinely blow it, again in a really well-written way–then that’s something they want to share.”

“’Fermi Paradox‘ was a great example of that, where people were just like, ‘Holy shit, this is amazing,’ and shared it with everyone.” Other stories can strike a more personal chord, like the piece on Generation Y. Urban says the audience response was, “‘I have all these feelings about Gen Y and millennials and, holy crap, you nailed that. You hit the nail on the head and you did it in a really entertaining way.’ I think that’s really what drives sharing.”

An appetite for stories that are less disposable and more like a good book–essays and articles you might even return to again and again–may help explain the rise of explainer sites, and of similar long-form content in other mediums, like the podcast Serial. But this kind of content is still marginal on an Internet tailored to generating churn-and-burn clicks; If you do want to see more quality long-form stories online, then Urban and Finn have a suggestion for you: Start writing it.


But how exactly do you do that?

1. Only write what you’re excited about

Urban says that long-form writing doesn’t only have to be engaging for the reader. If you’re writing something approaching 2,000 words, you better damn well be excited about the topic or else it will show–and your readers won’t be gripped enough to make it to the last sentence.

“There’s a lot of topics that would be good Wait But Why topics, except I don’t particularly find them either interesting, or I don’t think that I’m the right person to be writing it,” he says. “It has to be something that I’m giddy to dive into, that I can say, Oh, that would be a great Wait But Why article.”


Finn agrees. “I always try to encourage Tim to go back in the direction of what he’s really excited about, because that’s when the best work comes out. I think what happens is there might be a topic that seems right, that seems good, but the ideas aren’t coming together, and a lot of times I think it’s because there’s not a native excitement at the moment to write about it. It’s trying to marry what Tim’s excited about with what we think will be a good fit, what will get shared, and people can really engage with.”

2. Use images to support the words and not the other way around

Ironically for a long-form content site, the stick figure drawings often used in Urban’s essays have become an iconic staple of Wait But Why. But unlike the GIFs and memes that most viral content is built upon, the simple drawings in Wait But Why’s articles are there to support the words, much of the time adding humor that contextualizes a topic and strengthens the prose in the process. They also help to break up the long-form piece into easily digestible chunks.

“I try not to do a string of eight big paragraphs in a row with no visuals,” says Urban. “I try to make every piece very integrated with visuals and have the writing not be too dense. I’ll think pretty hard as I’m doing any topic about what could be better done visually in this post than writing. If there’s anything that can be better done visually, then I’ll always elect for that.”


3. Authenticity and hard work will get you an A++

“This is our big bet on the long-form content of the site: instead of trying to guess what the Internet will like or manufacturing a ‘voice’ persona to try to appeal to everyone, we instead just decided to be as authentic as possible, because nobody can copy that. We said, We’ll be the best at being authentic. If people like it, it’ll be awesome,” says Finn, who explains that authenticity is the difference between an article that is an A and one that is an A+ or A++. And, they say, that seemingly small difference can translate into exponentially more shares.

“It’s like power laws. An A++ is going to get shared 1,000 times more than an A+, which gets shared 1,000 times more than an A. Tim really gets all the credit because he has just this absolutely maniacal switch where he’ll put 40 hours into something and it will be an A, and then he’s the guy who has that extra 40 hours in the tank to pull two all-nighters just to turn it into an A++.

“It just gives that extra level of engagement that makes someone so compelled that they want to tell people about it,” says Finn.


4. A Corollary: Don’t Bullshit

Urban’s essays cover a wide array of lofty topics ranging from the vastness of time and space to religion to tackling social preconceptions about marriage. If you’re writing a 200-word viral post consisting mainly of GIFs, it’s easy to fudge your way through those subjects. If you’re writing long-form essays really meant to explore the nitty-gritty of the subject, Urban says do your research and don’t try to bullshit your way through it.

“The thing that’s scary about blogging is that I can say 15 things in an article, and if one of them is not quite accurate, 10 people who read that article will be experts on that one thing, and they will all throw a fit in the comments and make the entire article and the entire site lose credibility,” says Urban. “No one is kept more honest than we are at this, because we have enough readers now that know way more than I know about every single thing I write in every article. If I bullshit, I will get called on it.”

And anyway, doing your research pays off, like when one of the world’s most famous AI enthusiasts tweets that your article on the subject hit the mark.


Urban said the tweet was validating, especially because writing explainers can often be “scary.”

“I didn’t know anything about the Fermi Paradox before I started writing that post. I didn’t know anything about AI before I started doing this post. I’m relying on successfully educating myself enough in my research period to do it. And with AI, such a big topic, such a controversial topic, I had known so little about it before. I read a bunch and then wrote it. To have someone right away who knows a ton say it was a good primer and recommend it, it was just like this huge relief moment of, Okay, I didn’t fully botch this. This is not a disaster. I can just feel like, Well, Elon liked it. Maybe you didn’t, but he did.”

5. Don’t worry about sounding like an expert

In spite of the public appetite for expertise, there’s a value in being approachable, says Urban. “I think part of the appeal of our articles is you can find gurus writing about this stuff and that has its own value, but I think what people like about our articles is it doesn’t feel like they’re being written by a guru. It feels like they’re being written by their friend who just thought about this for 40 hours and are now discussing it with them at the dinner table.”

“Because it’s really no different from if I spent 40 hours thinking about why Gen Y is unhappy, for example, and then sat down with six friends at dinner, and I was like, Okay, I just spent 40 hours and here’s my little theory. They’d all be really interested. They’d be listening and then they’d have their own opinion. That’s all this is–a bigger version of telling my friends what I was just thinking about.”

6. Value your community and the trust it puts in you

While some websites–Popular Science, Medium, Quartz–have eschewed comment sections or removed them, partly for their lack of seriousness and abundance of vitriol, Urban and Finn see comments as integral to building a two-way relationship with their audience. His readers, he says, are “smart and curious and have long attention spans,” but also, “they’re all immature and fun people too–they have to be because I swear like a sailor. If people are too serious they’re not going to like the site.”

“So the thing that we just know that we can never, ever, ever, ever do is lose that trust in the community and lose their respect. We don’t want ever to let them down. That keeps us so incredibly scared and puts so much pressure on what we’re doing in a really good way and ups the ante. Whatever we do, even if it’s 2035 and we’re trying to do a movie, it has to be something that the community says, That’s worthy of the brand. That’s what matters.”


About the author

Michael Grothaus is a novelist, journalist, and former screenwriter. His debut novel EPIPHANY JONES is out now from Orenda Books. You can read more about him at