READ ON TO DISCOVER:
- How Tim Urban’s popular blog, Wait But Why, got so much buzz
- Which softwares and platforms spark different kinds of creativity
- What it means to stay authentic in an age of internet clickbait
Virginia Heffernan is a writer and acclaimed cultural critic whose most recent book, Magic and Loss: The Internet as Art, explores the deeply human aspects of digital culture. She recently sat down with Tim Urban, the writer behind the popular blog, Wait But Why, which features highly researched, hyper-longform prose on topics from procrastination to artificial intelligence, accompanied by quirky, everyman illustrations. Virginia and Tim discussed the origin story of Wait But Why, the nuance of all the different platforms on the internet, and the power of staying authentic.
This conversation has been edited and condensed.
Virginia: What is the story behind Wait, But Why?
Tim: Back in 2005, my friend sent me a link to his blog. It looked so professional and I asked him how [he] got something onto the internet. I didn’t understand that you could do that if you weren’t a professional coder or something. He showed [me] blogger.com. It was very surreal and exciting. At the time I had lamented that I couldn’t even find myself on Google. I was nowhere on the internet and it was a goal of mine to try to figure out how to get onto it somehow.
Virginia: I love that your first thought was “How do I get on the internet.”
Tim: It was like getting on TV almost, at least in my mind in 2005.
As far as writing goes, the worst thing I could be looking at was a blank Word document. It was a miserable place for me. But when I opened my first Blogger compose window, it was like I could do anything, I could be anything. I just lit up with creative energy when I saw it. I didn’t think I liked writing because I hated writing papers in college. But writing in my own voice on the internet in a way that had no consequences was just fun. Zero part of me thought this was going to turn into a career. This was purely to make my friends laugh and maybe strangers would find it—how fun would that be? It was an experiment.
Virginia: Something about the Blogger platform and the idea of blogging brought out this authenticity and productivity in you. I do think that you want to find software or a platform that you’re at home in: you might find yourself on blogger.com, you might find yourself on Pinterest, you might find yourself on a piece of paper, and these forms are very different. [What happened next?]
“You can be really hyperbolic with stick drawings. It’s amazing how much you can express with no artistic talent and only a few lines.”
Tim: Five years after I started the blog, I also had an online tutoring business. We had all these graphics tablets that tutors would use to do online whiteboards when they taught their students. I’m in the office late one night writing a blog post and I look up and see one of these graphics tablets on the shelf and I [thought,] “What if I draw something?” I was a terrible artist, but I thought that maybe that it would be kind of funny.
I had a beard at the time—I grow the shittiest beards. I was stroking it and was like “God I feel awesome” and then I look at myself in the mirror and my self esteem just plummets because I look like a teenager with a wispy mustache. I wanted to depict how that looks and how it feels. And what a better way to express that than a simple stick drawing? You can be really hyperbolic with stick drawings. It’s amazing how much you can express with no artistic talent and only a few lines. So the next five posts all had drawings in them.
Virginia: [There] are two things the drawings do for me as a reader. One, [I can] see what the tone is, because there’s something in those images that’s revelatory, because they’re line drawings, there’s nothing pretentious about them. And, [two,] it invites curiosity. And it’s just this very simple humor where it doesn’t cost you much to laugh at it.
With the New Yorker cartoons, for example, it brings out the connoisseur in you, makes you finicky, like “Not funny, funny, not funny, funny.” With Wait, But Why, I [felt I] was halfway into the joke. That nailed the tone for me.
Tim: Writing blog posts with stick drawings isn’t a normal medium—I invented it to fit me and likewise, [since] there’s so many platforms right now, you can find the right one to express yourself. The truth is, when you do something weird and unusual it goes over better, because it’s fresh and that gets people intrigued.
Virginia: It’s reductive to say the medium is the message, but on the other hand if you know you are doing makeup demo videos, you live well on YouTube, [and] when you’re doing stick figures that lives well in the blogging world.
All right, so what’s the third part [of the Wait, But Why story]?
“The truth is, when you do something weird and unusual it goes over better, because it’s fresh and that gets people intrigued.”
Tim: I stopped the blog for a couple of years, but in 2013, I decided I need to go full time on one of my creative pursuits. So I talked to my business partner, Andrew Finn, about it, and we came up with the idea of Wait, But Why.
He said, “Look, I’m going to get going on this and we’ll just see what happens.” I was taking it more seriously, and so I did procrastinate a lot more in getting this started. It took me months and months to get from the original idea to when the first thing was published.
Virginia: Now I see why you are part of the rich celebration of procrastination.
Tim: Oh my god. Horrible.
Virginia: You’re at the leading edge of procrastination.
Tim: I’m the Michael Jordan of procrastination.
So I started writing for Wait, But Why. I looked at the open empty WordPress doc and it was a different kind of energy. It was still a very excited energy because this could be anything, [so] I could make it really good. When I first started writing, I’d always written maybe 400, 600, maybe 1000 word things before.
Virginia: That was the convention of blogging.
Tim: Short, sweet. The idea at the time was [that] no one will read your long stuff on the internet. But part of the reason we started Wait, But Why is [because] it was frustrating how there was nothing in depth. There would be some new science thing and I’d really want to understand it, but it would be an unsatisfying, surface-level article. And I’d read ten other articles and they’d all be saying the same 600 words about it. Or it’d be something funny and it would be such a short list. I’d want someone to go into it. [When] you go to a stand up show, it’s an hour. It’s not six minutes of a David Letterman top ten list, it’s an hour Louis CK set. There were no good Louis CK sets or good science explainers or deep dives into psychology. When these rare longform pieces [did] happen and they were good, they made the rounds. That’s what we noticed.
People are starving for something really good. The hypothesis was if I just do my thing and I keep it light and entertaining with visuals and headings, but it’s thorough, I thought maybe this could work. I wrote the very first post, called “Seven Ways to be Insufferable on Facebook,” which sounds like a Buzzfeed listicle, and yes we were trying to get attention at the time with that headline, but when I wrote that I decided not to do the 600 word thing. It was a couple thousand words and it got kind of dark. I went into a deep dive into the psychology behind people’s Facebook behavior. The narcissism, the insecurity, and the image crafting that goes on.
Virginia: Do you remember an example?
Tim: I talked about the cryptic cliffhanger. It was the concept of someone basically saying “Wow, what a day, can’t believe the luck in my life.” And everyone [responds] like, “What happened, what happened?” They just want attention.
“The internet is the wild west of social interaction right now, and I think the etiquette is finally starting to form.”
Virginia: It’s funny, because that is not done anymore, and it’s partly [because] you start crystallizing this behavior. I got faulted for “Vague-booking,” once, [which is] when you give a line or two that sounds vaguely suicidal and everyone worries about you.
Tim: And a humble brag is another classic example. The internet is the wild west of social interaction right now, and I think the etiquette is finally starting to form. Not that etiquette is always good, but sometimes it’s there for a good reason so that we’re not our worst selves, our most self-absorbed, transparent selves.
Virginia: I like that it was important to you to lay down some parameters. Obviously it’s a super funny piece too, but one of the things that motivated you was how we are using this technology, how can we be better citizens here or funnier citizens here.
Tim: Exactly. I gave myself the freedom to go more in-depth. On Underneath the Turban, I never had the guts to take on more serious topics or go in-depth. But with Wait, But Why, I allowed myself to take myself just a little bit more seriously. I’m going to say something meaningful at the end of this post. The ability to go more in depth, and get a little more like real about stuff was the third ingredient that I think like made these posts what they are. That’s when I felt I found a unique art form, a unique medium that I really love.
“The ability to go more in depth, and get a little more like real about stuff was the third ingredient that I think like made these posts what they are. That’s when I felt I found a unique art form, a unique medium that I really love.”
Virginia: That flow state you got into is also the moment where the audience picked up. It’s the web fairy tale, that authenticity plays with an audience. There’s something in the software, something in having the experience and you just let loose.
So, so many trees fall in the forest on the web. I was talking to a museum curator the other day [for] a huge, famous museum, [and] they make incredible, beautiful content. They can’t get an eyeball on their site to save their lives. How in the world did your stick figures and innate curiosity bring people in droves to Wait, But Why?
Tim: I think that there is something to this low volume model. I spend minimum 40 hours on an article—I spent almost 400 hours on the Neuralink post. Not that hours purely equals good, but really thinking for dozens of hours before you even write the first word is valuable. It’s a luxury to be able to do so.
Virginia: You’re not hacking anything here. You’re actually just spending a long time writing articles like someone might at Rolling Stone or Vanity Fair.
“It’s the web fairy tale, that authenticity plays with an audience.”
Tim: It’s also an element of not needing the majority of people to like your work. You need a tiny, tiny minority of people. If one tenth of one percent of people happen to love your stuff… there’s seven billion people in the world, that’s seven million people who love your stuff. And those seven million are going to forward it to their friends and share it because they love it so much, because they’re the one in a thousand that likes it the most. So I’m just going to write exactly what I wish someone would send me.
