Tim, The Article

An interview with Tim Urban, the creator of Wait But Why, perhaps the most obsession-generating website on the internet, on what makes him tick.

By Catherine Sinow

Today in Tedium: The blog Wait But Why is the kind of cultural artifact that some people become intensely interested in, inhaling the website 10,000 words at a time. But unlike niche hobbies and internet corners, readers feel a great need to show WBW to everyone they know because, as a blog about the human experience, the topics feel so universal. Except I’ve sent Wait But Why posts to dozens of people and nobody has really cared. Half a million people read the blog per month, and I’ve probably never met any of them. As a person named Preston S. said in a Wait But Why Q&A: “As one of the many (I’m assuming here) people out there who read snippets of your posts to an unreceptive spouse …” Can’t argue with that, Preston S. Maybe it’s true that the best things in life are polarizing. Today’s Tedium is a trip through the exhaustive and wide-eyed world of Wait But Why and its author, Tim Urban—and this includes an interview, because I somehow got him on the phone. — Catherine @ Tedium

Today’s GIF is from Tim’s immensely popular 2016 TED Talk about procrastination, which at this time has 50 million views.


News Without Motives. 1440 is the daily newsletter helping 2M+ Americans stay informed—it’s news without motives, edited to be unbiased as humanly possible. The team at 1440 scours over 100+ sources so you don't have to. Culture, science, sports, politics, business, and everything in between—in a five-minute read each morning, 100% free. Subscribe here.

Tim Urban

Who is this guy? A quick explainer on Tim Urban and his site

Wait But Why is a blog (or, as their business-side guy calls it, a “content website”) with a loose, all-encompassing focus on the human experience and the natural phenomena that shapes it. Since 2013 it’s covered science, politics, history, technology, the concept of major life decisions, math, existential questions, travel, and uncomfortable social interactions. Its science breakdowns are fascinating, and its life advice is poignant and comforting. And occasionally, it dabbles in gripping sci-fi fiction.

The blog is written by a millennial New Yorker named Tim Urban, and this guy’s articles are long. I recall a tweet in which he criticized those “estimated reading time” widgets since his articles always show up as something like “124 minutes.” And yet, his style is so approachable and friendly that it feels like he’s an old friend giving you advice, and it’s written with a beautiful sense of awe about the world and universe.

The simple but effective stick figure drawings probably help with this. In a livestream he called himself a reverse Bob Ross: instead of beautiful works that take 20 minutes, he makes crude drawings that take hours. He uses the app Pixelmator and ranks his skill at B-. (He started out at F, not knowing how to use layers.)

Unnamed 14

Sage advice from Urban’s Twitter.

His relationship to his readers is in a very original class of social interaction: He once planned events for a bunch of Wait But Why readers to meet up, and people did it in 48 different countries. Some time before that, he asked WBW readers to plan his vacation. He ended up in Russia, Japan, Nigeria, Iraq, and Greenland.

“There’s not really a more jarring travel experience than spending two weeks getting used to being in Japan and then going immediately to Nigeria,” says the Nigeria post.

Tim has also done occasional Q&As in which his fans interview him way better than I did.

This is just one of many pieces of evidence that Urban is one of the most eccentric and intense people I can think of. You mostly see it in the way he runs his blog, but then there’s the fact that upon his future death, he is scheduled to be cryonically vitrified (frozen) with the company Alcor. The front page of Alcor quotes Tim Urban’s article about cryonics. (Cryonics is not particularly popular—only about 500 “deceased” people are floating in the suspension vats right now.) His reasoning makes sense—that it’s better to take a narrow chance at extended life than not try for it all—but since my worst fear is being digitized into an I Have No Mouth and I Must Scream land, I would never do it lest I be revived like that.

A WBW commenter claims they spoke with Max More, the President Emeritus of Alcor; More allegedly said that at least 25 people have signed up for Alcor because of the post. But there’s one person Urban has not convinced to sign up for Alcor—his wife, Tandice. (Urban and his wife are both self-starters—Tandice co-owns a boutique doctor’s office called The Lanby.)

Royal Family

An illustration of the devastating truth about second and third cousins. (all illustrations and graphics via Wait But Why; used with permission)

My five favorite Wait But Why pieces, in no order

  1. Your Family: Past, Present, and Future. Do you not know what a second cousin actually is? Urban explains it here, along with the jaw-dropping harmony of genealogy. Featuring a truly heartbreaking chart about how Prince Harry’s family line will slowly breed away from royalty.
  2. The Fermi Paradox. In which Urban explains fourteen possible reasons for why we haven’t met aliens yet. For some reason, I find it very soothing to read a long list of possible reasons for something and I was sad when the article was over.
  3. The AI Revolution. A two-parter about how AI is an existential threat. After poring over this for two hours, I promptly had an unforgettable anxiety attack that I believe was completely rational given the predictions in that post.
  4. The Procrastination series. Do you have a procrastination problem? This three-parter gently takes you through the whys and hows with characters like “The Panic Monster.” This article doesn’t mention ADHD at all, but it may as well cast Driven to Distraction aside and become the condition’s ultimate text. These posts were later adapted into a hugely popular TED Talk that he, naturally, threw together three days before he had to give it. It was the first TED talk to reach 10 million views.
  5. 20 Things I Learned While I Was In North Korea. Somehow, Urban was able to visit Pyongyang and a few nearby places. He presents a ruthless, hilarious dig at their government and he’s definitely on some North Korean watchlist now.

The tidbits and diversions that shaped Tim Urban’s life

Urban was born in Newton, Massachusetts. According to a WBW post, he grew up in “a have-your-cake-and-eat-it-too Reform Jewish family who also did Christmas and Easter.” In our interview, I asked him my most burning question: how did he get into Harvard?

“I got in because I got very good at a game that you need to get good at in order to get into the selective schools,” he told me. “And the game was you didn’t need good grades freshman year in high school. I got medium grades freshman year, and I knew that the game started sophomore year; that’s when you needed to get really good grades: sophomore and junior year and the first half of senior year. Each class had a game; in Spanish class, you have to memorize a lot right before the exam. In English class, you have to do the thesis statement the way the teacher’s asking for it.”

When he got to college, he “met a bunch of other people there who also were really good at the game. It’s not that it’s the smartest group of people. It’s a bunch of people who were awesome at this game.”

Underneath the Turban

Underneath the Turban, Urban’s first blog.

His first blog was called Underneath the Turban. It was active from 2005 (his first year out of college) to 2011 and it’s still up. “It’s like a tattoo of my old self on the internet,” he says. If you want to read the words of a youthful, unfiltered, informal Tim Urban firmly planted in the late 2000s, this blog is a must-read. Although he provides me with a disclaimer: “It’s a little less funny than it used to be because when I started dating my now-wife, I raced through and deleted all the curse words because her mom had found it.”

It’s an interesting place to take a look at his life story: apparently back in his Harvard years, he participated in a study where he was locked in a windowless room for 12 days. He did this for $3,500 to fund a personal trip to Asia. This entry makes it very clear that Urban has been truly himself for his entire life.

As he details in his posts and again to me on the phone, Wait But Why was a diversion from his tutoring business, which itself was a diversion from his film composing career. His blog debuted in 2013 with the help of his business partner and childhood friend Andrew Finn, who continued to run the tutoring business full-time until it got sold in 2021.

It’s possible that the most noteworthy moment of Tim Urban’s career was when he became friends with his personal hero, Elon Musk. Musk reached out to Urban after reading the AI articles, and he ended up writing a bunch of glowing, loving, lengthy reports on Musk, his companies, and the history of humanity and technology leading up to Elon Musk’s involvement (the post on Neuralink is almost 40,000 words long, longer than Animal Farm by George Orwell). His fans seem to be more into Elon Musk than not. On a WBW discussion post asking “Who would you bring back from the dead?,” two different people said that instead of bringing someone back, they would prevent Elon Musk from dying.

The Thinking Ladder: Tim Urban’s views on politics

Many people would be inclined to call Urban centrist. He deals lightly in Twitter politics, both pleasing and upsetting many of his ~700,000 followers with his opinions that could be considered both left and right wing. He occasionally has his formal critics, like in this article from the historically unethical website known as Gawker. And I must say that I think the article is pretty mean and poorly argued, despite its stylish prose.

I myself disagree with Tim Urban a lot of the time. I think he’s too positive about Elon Musk and has trouble acknowledging Musk’s controversial aspects. He’s been oddly silent about transgender issues, and one time he retweeted an article by a trans-critical guy who got banned from PayPal and Etsy for making stickers saying “There are only two genders.” There have been some other Tim Urban tweets that I didn’t like either, and as a left-leaning socialism subscriber, I’ve had my share of uneasiness and internal conflicts about Wait But Why.

But over time I have radically accepted this thanks to Urban himself: for the past three years, he’s preached extensively about political open-mindedness, critical thinking, and calm discussion. Gawker missed this—Urban’s main deal isn’t what he thinks policy should be, or about what political opinion he thinks the public should have. He is attempting to create a new, party-neutral frame of mind and way to talk about our society and its problems. And I love it.

This new frame of mind is the subject of Urban’s upcoming book, his first. The book is an expansion of his deeply complex “The Story of Us” post series, which covers the history of life, humanity, consciousness and society. He felt an intense, emotional calling to write it. We don’t know the name of this book yet (this Indian Amazon link makes it look like it’s called The Story of Us), but it’s hitting digital shelves in February of 2023. The majority of it will be new writing about current events, seen through his invented framework of thinking.

Thinking Ladder

Tim Urban’s “Thinking Ladder,” depicting in descending order “thinking like a scientist,” “thinking like a sports fan,” “thinking like an attorney,” and “thinking like a zealot.”

To simplify one of the densest things I’ve ever read: a central theme in The Story of Us posts (and apparently the book, too) is Urban’s own 2-D political compass that he created. It portrays a horizontal spectrum of ideas and opinions (left versus right, at its most broad example), but there’s also an up versus down. Urban calls this the Thinking Ladder, with its extremes called “high-rung” and “low-rung”. Here he’s drawing a distinction between discussion-oriented critical thinking (led by the “higher mind”) against the jump-to-conclusions, tribal thinking from our ancient “primitive mind.”

(There’s also a 3-D component to this political compass, but that’s best saved for when you’re ready to take a 3-hour political analysis journey.)

“For the politically homeless people, a lot of the home they’re looking for is actually not in the center,” he told me. “It’s actually above.”

The mention of low-rung tribal thinking naturally implicates woke culture—he criticizes it on Twitter sometimes, so I asked him about it. I ended up agreeing with him more than I thought I would when he said, “Conformity PC has skyrocketed and its ability to shut down discussions is much higher than it was 10 years ago. That’s what got me into thinking, I need to write about this. Now. I’m wondering, why are they succeeding more? What is that success made of? It’s not okay, given that we are in a rapidly advancing technological world, and the stakes are getting higher for humanity as our tech gets more powerful. We have to be able to think collectively.”

Although it sounds like he dislikes the far left, he really just dislikes low-rung left thinking: “We want a radical left voice in the room in the high-rung political arena. That’s good, maybe liberalism is wrong about some stuff. What I don’t like is when this group chills the entire conversation and says, ’we are 100 percent right, we have a monopoly on moral good, and anyone who disagrees with us are the bad racists from the ’60s fighting against Martin Luther King.’ It’s a cheap trick to make it scary to disagree with you.”

I didn’t ask him about his dislike for far-right republicans because his anti-Trump posts made it feel obvious already. He did toss off a casual insult at CNN, though.

How has his view on artificial intelligence evolved?

I followed up with Urban on the state of AI, as it’s been seven years since his anxiety-inducing posts. I still masochistically read them once every six months or so, contemplating its suggestion that in our lifetimes, the world may be eaten by uncontrollably multiplying nanobots (this concept is called Gray Goo).

On the phone, Urban expresses both deep fear—“We’re going to have a lot of unexpected, unforeseen consequences, some will be negative and scary”—and a sense of hope—“my gut suggests that in 2060, we will be happier.” He also expresses, most unexpectedly, excitement.

AI Revolution

A graphic from Urban’s The AI Revolution.

“I want to have sensors in my body and my genome totally understood by an AI and, and it’s reading all the levels of my glucose and my heart rate and my blood pressure,” he told me. “And it knows when I ate last and what I ate and what my goals are, and it’s advising me what to eat and when to exercise. And I know that its advice is perfect. It’s way better than any advice I can give myself or any advice a trainer or dietician could ever give me because it knows all the details. In 2060 cancer will always be caught really early because AI knows what’s going on in your body. No one’s going to want to go back to a world where you just went in for a check here and there and hope they didn’t find a tumor. That’s going to seem really old school.”

This lines up well with Ray Kurzweil’s utopian cyborg dreams. (Kurzweil, futurist and inventor of the flatbed scanner, is discussed extensively in the AI posts. There’s also a Tedium post about his work with Optical Character Recognition.)

I asked him these questions a little bit before people started talking about AI art, and recently ChatGPT has been unleashed. His answers would probably be mostly the same if I asked him now, but now everything he said on the phone in April reads a bit more urgent.

“AI already does so much for us,” he told me. “Google Maps is incredible. We forget how much it used to suck to have to look at maps and figure out where you’re going. So many safety things in cars and airplanes are just because AI is running it and doing a really good job.”

Google Maps is truly incredible. Streetview is absurdly creepy, but we’re used to it—maybe this is the key to adjusting to AI. That is, until it becomes so smart that the world might dramatically change every six hours. I try not to think about that.

This article was hard to write. I procrastinated on it a lot. The main problem was that I kept going back to Tim’s articles for research, and then I ended up spending 2 hour blocks reading Wait But Why. But this is just a 3,000 word article. I almost never dream of writing a book. Tim Urban has accomplished something very difficult.

Dark Playground

The “Dark Playground” that procrastinators get stuck in while attempting to be productive.

Since he is perhaps the world’s most famous procrastinator, I asked him how his problem has affected his writing process. Procrastination has been a huge problem with his book:

It took me a long time, but I also ended up with a very long, 200,000-word first draft, which is way too long, double the length of a normal volume book. I ended up both taking forever and creating something way too long, which doesn’t make sense. And you can’t just cut sections, you have to rewrite.

Urban is very grateful for the patience of his readers. “For me,” he said, “I don’t want to ever do a grand dissertation of the world again like I did for this book. It’s not a good match. In the future, it’s either going to be blog posts, or short, modular books with individual little chapters.” I pointed out that this is exactly what a lot of people say before going on to write another book, and that he is probably one of these people. He agreed with me.


Thanks to Tim for taking the time to chat with us—and to Catherine for writing a killer piece! Find this one an interesting read? Share it with a pal!

And thanks again to 1440 for sponsoring. If you’re looking for a little more unbiased news in your inbox, a signup to the 1440 list is just the place to start.

Catherine Sinow

Your time was just wasted by Catherine Sinow

Catherine Sinow is a nonfiction writer in Portland, Oregon, originally from San Diego. Her writing focuses on obscure and idiosyncratic topics. She is a graduate of Colorado College, where she studied creative writing, art history, and metalworking.

Find me on: Website