I first got to know Tim Urban’s site, Wait But Why, when reading one of his most popular posts from last fall: “The Marriage Decision.” In a nutshell, this long essay is about why it’s so difficult to make the choice: to marry — to not marry — to whom? It’s summed up well in one of Urban’s signature stick-figure graphics: a scared couple shivers between two infinite abysses labeled SOUL-CRUSHING BREAKUP and PERMANENT MARRIAGE TILL YOU DIE. I think about this post once a month, every month.

“The Marriage Decision” has had a tangible impact on my life; my best friend — having read it at my behest — dumped her long-time boyfriend and got married to someone else, two months later, in a kitchen. When I told Tim this story, he admitted it’s the third Wait But Why-related break-up to which he’s been privy.

So add that to a list of phrases to describe Tim Urban: blogger, researcher, interviewer, creator of charming stick-figure cartoons, couple breaker-upper (but in a good way!). You should really know him. He’s the writer Elon Musk reached out to with the goal of capturing his complex projects — from Space X to Tesla and now Neuralink — in a way that the non-rocket scientists among us can understand.

The Musk articles have brought even more attention to Wait But Why, but the site has boasted an impressive, dedicated and global following since its start. And the reason is clearly Tim Urban — his curiosity, his foresight about his business’ place in today’s media landscape, and his innate ability to zero in on things we all understand for which we often lack the words.


When you were growing up and going to school, were you imagining yourself doing something like Wait But Why for your career?
I definitely was not planning on drawing stick-figures online, no. I think I would have said that writing was a possibility. I moved to L.A. to write film scores after college. And I thought I could maybe do something in business. I didn’t really know for sure. But I knew I wanted to start something. I didn’t want to go apply for a job. I wanted to start my own world of some kind.

My main thing before that was starting a test-prep company… It became full-time, partnered with Andrew [Finn, co-founder of Wait But Why]… I liked having a business but I really wanted to do one of these creative things full time. So about four years ago, I said, okay, you need to pick one thing and just do it, all in.

You’ve found a big audience in a relatively short amount of time. When was the moment when you got a sense that this was something that people really connected with and that it was going to work?
The very first post, I just posted on my personal Facebook, because there was no other platform to post it on. It ended up bringing about a half a million people in the first month. It was good to know that the hypothesis might be correct: that if I just spent 60 hours on one post, just really work hard on each post rather than have a large volume, that post has a good chance of standing out.

But then I wrote a post about millennials, what I call “Gen Ys.” And it seemed to hit a nerve or something. Because like, two months in, that post just absolutely exploded. The first one had 500,000 people in a month. This one had 10 million people in a week. It was like, “the blogger dream.”

We didn’t have a plan. My plan was basically to put my head down and write really interesting things, and just kind of go from there.

After four years of developing this community, do you think about your readers more so when you are writing, or are you mostly still guided by your own curiosity and just hoping that others will come along with you on that journey?
I think in some ways it’s more about my own curiosity and less about readers, now that there are more readers. At first we didn’t have anything at all. No one is paying attention at first, so you’re really concerned about that. And now I find that, especially since I know there’s no way I can please all the readers — every single post that I write there’s some contention, people get upset or angry or bored — I just make sure I focus on what I want to write. On the other hand, obviously there’s some level of having a bigger audience that’s in your head a little bit. My problem is that I’m a perfectionist. And I just take forever. I just want the post to be exactly what I want if I’m going to send it out to all of these people. There’s some kind of mix of caring more and caring less than I used to.

It seems like this idea of quality over quantity is very important for Wait But Why.
Oh yeah, for sure. That’s what the whole brand is based on.

It’s kind of a, I don’t know, anachronistic way of creating media now. But actually, it probably helps the site to stand out quite a bit.
Yeah, exactly. I felt like that was a part of the problem — that it was so rare that people were doing that model. Most of the content is put out by these big companies that were venture-funded and have lots of writers putting out stuff. And that was part of why I said, “We’re definitely not going to out-BuzzFeed BuzzFeed.” We can’t beat these people at their thing. We have no way to get that kind of volume out. But what we can beat them at is, I can spend longer on an article than any of their writers ever considers spending. And so with a small amount of quantity we can make things that stand out.

I know you’ve now interviewed Elon Musk several times. Aside from the sheer density of the topics, was it challenging, being asked to write about something like this, and was it strange to step into the role of an interviewer?
I mean, it felt like it was the right thing for the site in that these were all topics that I wanted to write about anyway. I really wanted to write about energy and space travel, Mars. I always wanted to write about the brain.

When he reached out, it was very open-ended… And that allowed me to kind of craft this project in a way I thought worked best for me and that would also excite him. To write really thorough, in-depth, accurate posts on these very complex topics — for all the things that he has going right, I don’t think that they get their message across as well as he wants them to… And that’s reasonable, because it takes a lot of explaining. There’s a lot of background information that you need, to understand why it matters so much. I wanted to be able to do this post on Wait But Why and not on any other site, and he seemed down for whatever. So I got access to him and a lot of his executives and engineers to just really ask questions.

A lot of it was just like a conversation I would have with any friend who knows a lot more than I do about something interesting. I just get naturally curious. I read a bunch of stuff online as well, read a bunch of books on the topic. I wanted to really understand what was going on, and that’s when I would turn and write this thing. They were huge projects. I learned so much about the world from them.

Does any one of your posts stand out to you, in terms of something that was really personal to write about?
There are a few posts that I find myself referencing again and again in other posts, and that I find myself thinking about a lot. I end up doing talks on those topics; there’s some fundamental lesson there. One of them is called, “Religion for the Non-Religious”… “Atheist” means you’re not something. But you still need a framework. You still need a way to grow… So it’s a post about mindfulness and awareness and all of that.

The Cook and the Chef” is a post about originality and [Musk’s] “reasoning from first principles,” versus copying what everyone else is doing, and just assuming that “this is the way the world is, it must be for a good reason and don’t try to change anything.”

Another one, I would say, is a post around procrastination, which is kind of like my core struggle. And it definitely has become, I think, the most referenced post by readers. I get a lot of emails about it… Those are kind of defining things for the site.

Do you hear a lot of responses to your posts, ways that they’ve changed people’s lives?
I’ve definitely heard some amazing stories, like about a kid who’s sick, who is loving the blog and it’s making them happy — things like that are obviously incredible to hear.

Sometimes I’ll do a talk at MIT or somewhere and I get told by a kid afterward that he is going to work at Space X next year, or work in A.I. next year, because he read a post. I think if you can convince a smart, young person to dedicate their career to something, that’s like adding fifty years of effort into that cause. That’s a massive impact.

I was reading one of your posts about the rapid progress of technology, and how it would be shocking to someone from the past to see where we are now. I feel like that could also be said for our political climate in the U.S.. Things are changing so rapidly and something absurd seems to happen every day. Do you feel a new pressure to write about politics now?
I actually am currently in the middle of a long post about politics, but even more so: the way we think, the way we figure out people who disagree with us. That post was triggered half a year before the election, actually, when I felt like I saw a lot of this around me, with people who were just, a full tribal, dogma-following echo chamber. And I thought, this is kind of nonsense, this is not going to end well if this is how we’re thinking. So that’s what started it. And since then the news has definitely validated the thoughts that I had about this topic, unfortunately.

You also wrote a piece right after the 2016 election, “It’s Going to be Okay” and then a follow-up shortly afterwards. It seemed like just in that short amount of time your perspective had shifted. Has it been difficult keeping up with this topic?
Yeah, definitely perspective is shifting all the time, for me and for everyone else. That’s why it’s hard to write this one long post. I keep changing my own thoughts on it as I go. I think I just need to get it out.

And you were on The Apprentice some years ago.
That is true.

Is it a bit surreal looking back and thinking about that time now?
Yeah, it’s pretty odd. But in some ways, you don’t really get to know him better on the show than you do watching it, so I feel like, it’s as weird for anyone who watched the show as it is for me. But maybe I’ve just blocked it out at this point.

What else is on the horizon for you and Wait But Why?
Well, I’m starting a podcast in the fall. And then I’m going to also write a book next year. That’s kind of a whole different thing, although it’s not that different — it’s kind of the ultimate blog post.