BERRY LIBERMAN: Did you really do your college thesis in three days?

TIM URBAN: Ninety pages, senior thesis, yes. I did. I started word one 72 hours before I handed it in. It was not a good experience.

[Laughs]. Did you pass?

They say that the ideal thesis isn’t just a summary of stuff, it adds to knowledge. And mine was not adding to anything. I passed though.

You did it in three days. So that’s kind of awesome.

Well yeah, but it was a battle with procrastination. And that was an extremely bad project for me because it was just huge and disgusting. Who wants to work on their thesis? It’s upsetting. Although my job now is basically writing papers.

I was just going to say!

Yeah, I don’t know why I did that. But now it’s fun because A, I can pick the topics and do what I want. And B, I can write in a fun way with illustrations. Now I get to post it and there are readers. That makes a big difference.

That’s interesting ‘cause you sound a lot like me—lazy but ambitious.

Exactly.

And you also sound like me in that you’re extrovert, not introvert. So the audience matters.

Yeah that’s also true. Writing for me, the whole point of it is that I’m communicating with “blank.” And if there’s no “blank,” it’s less purposeful. I’m not going to write what I think is a beautiful passage and just keep it like I’m Emily Dickinson. That’s not me. If I’m writing, I’m doing it to delight someone. It’s like if you asked someone who gets onstage, a speaker or a stand-up comic, to just go do it alone in a closet. And that’s their thing. They wouldn’t be gratified. The point of stand-up comedy is to make people laugh. So the other end of the chain is a critical piece of the puzzle for me.

I keep trying to explain “Wait But Why” to people here. I say, “It’s like falling inside a giant mind and it’s funny in there, and there are big topics that you would never ever unpack yourself, and there are stick figures.” [Laughs]. But I want to know what’s your pitch?

I think that was as good a description as they come! I don’t know how I would describe it better. Just saying, “Long-form but stick figures” is enough to get people to say, “Huh?” Once they get those two things together then they usually start to understand. It’s like, “Long but kind of silly.” And the topics can be serious and deep or they can be explainers or silly topics themselves.

[Laughs]. I watch your TED talk, which has had so many views and is brilliant, and I’d love to know, what are the key parts of your story that got you to Wait But Why? Because so many things you write about are incredibly deep, very thoughtful and personal. But there’s no “I” in it. There’s no backstory to how you got to explore, for example, how to pick your life partner. That’s a brilliant post and I love it so much. Those stick figures—Romantic Ronald and Fear-Driven Freda. They’re the best. How did you get to be exploring these topics?

Again, to bring up stand-up comedy, I’ve heard someone say, “Everyone can be a stand-up comic if they just write down every time they have an interesting or funny observation.” It doesn’t have to be outright funny, it can be something like, “It’s so weird this is not consistent or, why do we do this but we don’t do that?” We all have these thoughts. And you also train yourself to look for those thoughts, and then you write them down. It’s about figuring out the exact funny wording, so of course there’s a talent there too. But the material comes from living life as a human. And so I would say the same thing about myself. I’m 34 and I’ve thought a lot of thoughts in my 34 years and I’ve had a lot of conversations and experiences just like anyone else. But my job is to think hard about things in life, important or interesting topics, and then draw on all those thoughts. You know, for that post “How to Pick Your Life Partner,” that stems back to long conversations I would have with my high school friends. And then when I went to college, I remember having a long conversation with these two guys about the things you actually need in a life partner. And then I remember sitting on the steps at Union Square with a friend after a movie and he was trying to decide whether to marry his girlfriend. And I’ve seen a lot of my friends in relationships and I’ve been in relationships and I’ve seen things there. So when it was time to do the post, it’s not like all those thoughts were clear in my head. It’s that I sat there for a couple of days and thought about everything. What are the things that are ideally counterintuitive? What are the mistakes we all make? I think about my friends—“People shouldn’t do this, shouldn’t value this so much in a relationship, or they forget to value this.” And I think about my own experiences—“What was I surprised about when I was first in a serious relationship? What did I see in my parents? My parents are divorced. Interesting. Why? How did that start?” And so you do this and then you start writing it down and you begin to see patterns and then you categorise those patterns and then you have a blog post. And you write it.

Have you ever been in therapy?

I’ve been in therapy.

Does that inform it? The things that you articulate, are they something you’ve unpacked with friends at Union Square or are they personal journey work? Has that played a big part?

Sure. I mean personal journey in general for sure. I haven’t done very much therapy. I’ve done a year or two, spread apart. And I would certainly say I do that kind of stuff all the time. Alone and with friends and with my girlfriend, I’ll expound stuff. So therapy is not like “the” time where I figured everything out.

So, if you’ve got a topic, something epic that you want to really pull apart, is there a go-to person or a go-to top five?

It depends, you know, on the topic. There are lifelong friends. My business partner who co-owns Wait But Why with me, Andrew, we’ve taken road trips together, try to always talk about the big questions. And now I’ve been in a relationship for five years. My girlfriend and I talk about this stuff all the time. And then I have two sisters who I’m really close with and we talk about this stuff. It’s not all I’m doing, only talk about deep things, but if I’m with one of these people for an extended period of time there’s a good chance we’ll get into this stuff. ‘Cause we’re all a similar age and we’re all figuring it out together I think. But that’s intentional. Those are the people I surround myself with intentionally, ‘cause those are the people I have the most fun talking to.

So how did you get here? Like, how did you get to writing the blog? ‘Cause you’re a Harvard graduate, right?

Yes. Yes. Harvard graduate and knew he didn’t want to do something boring. Knew he wanted to do something creative. Something in, like, the arts of some kind.

What was your degree?

Government.

Okay.

For no good reason.

[Laughs]. Okay.

And so I moved to L.A. after college to start writing movie scores. I was going to write music, it was the thing I wanted to do the most. I was trying to figure out a career with that, and movie scoring seemed like a good one. And I started tutoring on the side. I was tutoring students after school for their homework, SATs, stuff like that to pay the bills. Which is a typical thing someone in L.A. would do who is trying to do something in the arts but wants to pay the bills and doesn’t want to be exhausted from work, so it’s a good job. But, you know, the film-scoring career, there’s no specific structure. You have to just go and start figuring it out. So 22-year-old Tim—total procrastinator—never did anything. Once in a while I would get a movie job from a friend who would know someone and I would do really well. I think I was good at it. But you had to really build your career and it just wasn’t fun to do at all. I didn’t make that much progress because instead I started tutoring like crazy and I started getting more referrals; I never turned anyone down.

So I ended up starting a tutoring company. That was 2005. And then I partnered with Andrew, my current business partner, in 2007, and we built it up for six years. I moved to New York in 2009.

Meanwhile I’m writing a piano album on the side, I’m blogging on the side—I wrote another blog for six years. I moved to New York and started this program called the BMI Lehman Engel Theatre Workshop, which helped partner people who were writing musicals with other people. If you’re a composer you partner with lyricists and then you workshop. So I was really into that. I was doing that with a quarter of my time, blogging with a quarter of my time, working on the business with half my time, doing everything badly. ‘Cause that’s what’s happens when you put a quarter of your time in. And so I still never lost that impulse that I had in college to do something creative full-time. Finally in 2013 I said, “Okay, I’m going to figure this out.” So I talked to my business partner and we brainstormed cool businesses where he could do his thing and I could do something more satisfying. ‘Cause I was going crazy here doing these things on the side. So we brainstormed things and realised that I’ve been blogging for six years and I really like doing it. I was putting five to 10 hours a week into it. What if I full-time blog? Just obsessively worked on the blog, tried to make it the best one I could? That could turn into a platform, we could hire other writers maybe. We could end up writing a book from it. Like, there’s a lot of things that could happen from that which are enticing from a business standpoint. And so I was very excited about writing because it was only second to music in the things that excited me. So that was the idea. In 2013 I stopped working at the other company and gradually my other work. And I said, “I’m going to go full-time right now. For the first time I’m going to focus on one thing.” And unlike my film scoring career, A, I was a little more mature, a little better at getting things done. And B, I had a business partner who was counting on me to work on this since I wasn’t working on the other thing, so I had some external pressure. And I started by going to Easter Island to just write. I wasn’t that productive. I wrote three articles. And one of them I thought was good enough to post, so I got back and actually started the site. Even then I procrastinated for six months on really getting it going. But I finally got it up and I was fortunate that it took off pretty quickly. The first article did really well. And then 10 articles and two months in, there were numbers that completely blew up and put the blog on the map.

Which one was that?

It was called “Why Generation Y Yuppies Are Unhappy”.

[Laughs].

And that was, again, an article from many conversations from my own experience. A lot of that experience was from working with students. When I was a tutor I worked with a lot of millennials and I think I understood their psychology.

Why are they unhappy?

There are three reasons. One, they’re super ambitious. They think, I’m going to go far and achieve all of these things ‘cause their parents are fancy baby boomers who did really well in a really good economic time and their parents raised them saying, “You can do anything.” And they had a normal nine-to-five nicely-paying job, which is not enough for most millennials. This demographic was raised thinking, I need to do something special with my time. Not just lucrative. That’s the first thing. Then on top of that there’s the classic millennial thing where they were raised to think they were even more special than everyone else around them. A lot of people are like that. So then they get to the real world, which is of course really hard, and it takes years to build up a really good career. Especially a special one. It’s really hard. And when you graduate college you’re not very special. It doesn’t matter how awesome you are. You’re an intern somewhere. You’re not very good at anything. And you’re not that valuable to any company unless you’re an unusual genius so you have to just bust your ass for a while and it’s not pleasant and you don’t know if it’s going to work. And then on top of that they look on Facebook, ‘cause you have social media now, and they see all of these other friends of theirs projecting the best view of their life. And everyone’s life looks great on Facebook. And so they think everyone’s more successful and happier than they are. So then they really feel extra bad about themselves. And then you add to that a bad economy, it’s the perfect storm of misery.

[Laughs].

And, you know, I said at the beginning of that post that

So if your expectations are sky high and reality can’t match that, you’re going to have a negative happiness. So that was that idea. But the post totally blew up. I made 300 email subscribers before that post, and then 10 days later there were 30,000.

Ho-oly shit!

The post was everywhere for a while. I mean every single person I know was like, “Oh my God, your thing!”

Hah!

So that was cool. And because now there were readers and there was an email list, there was motivation to really keep going. And I never trimmed back. It was obvious I was going to dig into this for a while.

How was that in your head a business model though? Did you just leave that to your business partner? “Mate I’m going to give you the content, you figure out what to do with it.”

No, ‘cause he was working full-time on the tutoring company. The idea was if there’s an audience, then there are plenty of ways to make money. You just have to be creative about it. So, you know, the classic way is banner ads but we didn’t really want to do that. A few months in we started a store selling t-shirts, stuffed animals. Stuff that was enough to pay my salary.

Hah!

So there’s that. Then there’s a bunch of other costs, so for a while the company was using money from the other company, which is a nice way to get started. So the store then took a lot of that off the plate. And then we started getting reader donations from a site called Patreon. We set it up, people can do a monthly recurring pledge. And so those two things combined was enough to support me and an employee and all of our costs. Break even. And then on top of that I started to do some speaking, which helps. That brings in some more. It’s not huge but it’s enough. All we wanted was enough to be able to grow this and do it for a long time without having the stress about money.

And it doesn’t also hurt that now, you know, if we start something else there’s a mouthpiece for it. We have a nice media platform. So it can serve us in a lot of ways, and mostly for me it’s just that I’m doing something I really want to do right now. I couldn’t love writing “Wait But Why” more. It’s exactly what I want to be doing. It’s interesting, I get to learn, I get to use my tutoring skills and explain stuff. It’s just this wide-open platform, I can use it creatively for different things depending on what I’m interested in. So I couldn’t ask for more. I feel like the luckiest person to have this platform right now and hope it sticks around.

If I go back to what you described about millennials and how they have this inflated sense of self, and then there’s the humble walk through the mud of life. What was that for you? ‘Cause in your writing, it feels very humble. There’s an enormous amount of humility in the writing even though you’re dealing with and up against huge topics.

Yeah, I think it helps that I don’t feel like I’m an expert on anything. I do feel like every topic I take on I’m a total amateur right when I start. So two or three weeks later, after my research when I’m writing it, I’m not fully like, “Oh well I’m the pro at this!” I’m like, “I know exactly what it’s like to not know about this.” It’s as if I’m going to dinner with a bunch of friends and saying, “Listen to this stuff.” And I can explain it ‘cause I know exactly where they are and what was interesting to me about it. Versus if you’re an expert on something then you use the jargon, and it’s harder to explain stuff. I think another thing is that I still just think I’m a blogger, there’re people doing much more important things. My friend’s a surgeon. I’m using this computer that people actually know how to make. And what I’m doing is I’m benefiting from a society that is built and incredible, and I now have the luxury of making a living writing about stuff that I like and I get to find all the intellectual, curious people in the world who like that stuff. So I just feel very lucky to be in this situation. And also I think part of it is the millennial thing. I spent the ages of 22 to 31 not liking my life very much. And I had an objectively good life. Like, I was running my own business and everything. I guess I’m just saying that, after spending nine years not doing what I loved, I was mad at myself for that. So it wasn’t, “Oh it was so hard to start a career that I liked.” It’s that it’s hard emotionally to just do what you really want to do. Especially when it’s not conventional. So I appreciate just how challenging it is to do what you know you should be doing in life. Plus I think my readers are damn smart. So I’m always trying to not have the readers read it and say, “This guy’s an idiot.” As soon as I meet readers and they’re clearly very intelligent people, that makes it nerve-wracking. So I guess I just feel like I am one of the readers in many ways and I’m the lucky one who gets to be the one writing all this stuff.

Two questions on that. The first one is: why do you think it’s emotionally hard to do what you know you should really be doing?

I think it is incredibly hard because there are two characters in our brain at different times. One is very logical and says, “Well nothing that bad is going to happen if we do this and fail, just try it!” And like, “Oh people say it’s one in a hundred, but if you actually just do the thing it’ll probably work.” And then there’s the other character, this more ancient emotional character, who’s scared of a lot of stuff and doesn’t want to take any risks. Scared of what people think of him. And is unsure of himself. And procrastinates and says, “Yeah, I’ll make that big life change, just not this week. ‘Cause I’ve got stuff right now.” And you’re just battling at all times against this emotional fear-based animal, and this very rational, calculating consciousness in your head. And it’s one thing if you’re one of these rock stars who feels like you have nothing to lose and you just grow up in a bad situation—it’s easier for them to take risks because the illusion that they’re on some platform, that life is supposed to be perfect for them, is not even close to being there. But

I just think it’s a challenge for a lot of people. Not everyone, some people are good at it.

Or maybe as you said in your TED talk, they’re just good at one part of it and they’re hiding in other places.

That’s right. Exactly. That battle in the head affects almost everyone I think. For some people it’s procrastination, some people it’s an eating problem, some people it’s a promiscuity problem. It just depends.

So the second question was: how did you write 30,000-word articles in the age of the Internet? How did you think that was going to fly?

Build up to it, you know. The first ones I was scared to go over 2000 words and then I did one that was three! And each time I went, “Oh! Not only did it not backfire, I think people actually really like it.” I got really good responses. And so I got encouraged to say, “You know what? Maybe this is okay.” One time I wrote a post and someone asked a question in the comments, and I answered. I said, “Actually I had written a whole thing about this but I took it out ‘cause I didn’t want it to be too long, but here’s the answer.” And someone wrote back, “We love your stuff! We want to read everything you do! Don’t cut things out!” You know. “You should always make it longer!” And these articles are visual and they’re light. And they’re on interesting topics. It’s not for everyone, but the group of people who it’s really for, they want to get the full information.

So you’re doing all this awesome stuff. What’s your kryptonite? What’s the thing that will really set you off your game?

Oh I mean the TED talk is not a lie. I ruin my own life constantly by procrastinating. And procrastinating in many different, clever ways. Sometimes I’ll research way too long. Sometimes I’ll write a bunch of emails and they’ll be way too thorough.

But wait, one of my favourite things on your site is “The Shed.” Because it’s like you’ve taken all of your procrastination and made it a thing that everyone can relate to. For me, procrastination is actually feeding the work, because you can’t be on all the time, right? So all of those hilarious video clips in the shed on your website and all of that, it’s all part of the same brain space.

Maybe, but I will say that I’ll spend eight hours in my day trying to get started. And then I’ll spend eight hours working. When instead I could have spent eight hours working or four hours trying to get started, eight hours working, and then I could have time to see friends. To go out to dinner with my girlfriend. To read a book. To do things that also make me happy. But that time is gone right now because I have a genuinely busy job and I’m not very good at being productive. Because there’s no adult here to make me do it.

So whose life do you admire? Like, who do you look at either personally or in the world and say, “I want to actually be like this person holistically. I like the way that that person walks in the world.”

You know Seth Godin?

Yeah. We’ve interviewed him.

So he’s prolifically productive. I read his blog for a long time and I had a chance to go visit his office. And he just seems like a very grown up man who both has an inner child and is super productive. He has this great little office and staff. But he also probably takes weekends off and has this great passion. He makes wine, he makes really great coffee and he’s really into cooking. And I just think this is someone who has found balance and is prolific in his creating. So I think that it’s possible. And I think those people I admire, people who I’m like, “Wow, you’re doing awesome stuff with your career, and you reject the notion that that’s all that matters, that’s all I can do.” I think those people are psychologically stunted in many ways. Those people who are great, great, great—they’ve basically sacrificed everything for it. I think that we can do better than that. Humans should be able to do better than that. There are movie stars or famous writers, and then you hear they’re kind of a bad father. Or they can’t hold down a relationship. Or you find out they don’t have any close friendships or they die young from mistreating themselves. Some people worship those people, you know? But

Part of the wisdom is that they would have been greater if they had sacrificed everything but realised that it’s a better life move to have the balance part of it and then do something great for other parts than to just go completely crazy and try to be the number one in the world at something. That’s what I think. So Seth Godin is one example of that.

That’s an awesome example. And you used a really interesting term, which keeps ricocheting in my mind, you said, “He’s a grown up man.”

Yeah, I know lots of adults who are absolutely not. You find these adults who namedrop or brag or who are being bad fathers, which are childish things to do. You know? Cheating on your husband is a childish thing to do. And being some really awesome, incredibly famous hundred-millionaire CEO who’s just working all the time, I see that person as a child who needs to be hugged and counselled.

It reminds me of this film Lions for Lambs. Robert Redford is the professor and he’s talking to one of his millennial students who’s there on a scholarship and he’s flunking. And there’s this moment where Robert Redford is trying to convince the kid that he needs to make an effort, because the Mercedes at the end is not the reward. He needs to actually be engaged. And he says, “Adulthood has already happened when you’re 12 decisions in.” Like, it’s happening anyway, you’re already the amount of decisions you’ve made in. Whether or not you choose to actually become a grown up and embody that.

Yep. It’s very hard. One of the greatest challenges in life is becoming a grown up. And again, some people never get there. Some people don’t even realise that that’s the game. They don’t get that they’re not an adult.

Okay, so that brings me to this question that I was like, “Do I ask this of you or not?” But I’m going to. You wrote that Elon Musk wants to populate Mars with a million people. And I’m incredulous at the scale of the vision for a thriving multi-planetary civilisation. But what about the inner world? The fact that we’ve so royally destroyed this planet because we don’t understand ourselves and each other? Who are you going to interview about that?

Well, Elon makes the point that taking care of the Earth matters even more, and I totally agree. I’d like to talk to some people in education. Trying to fix education is one of the greatest possible challenges I can imagine. The work with Tesla is a huge project, they’re a company that’s making some great changes in the world. I’d also love to talk to Mark Zuckerberg, he’s giving 99 percent of his wealth away.

What do you think about that? About business that can have no ethical responsibility to community or the planet, and then use philanthropy to plug up all the holes that business screws up? I just find it a hard paradigm to get over. Like, Facebook is a business that makes a lot of money and has cool technology around it but doesn’t have an ethical overlay. And then Mark Zuckerberg amassed a fortune and now he’s going to donate it all. We have no expectations of people in business. They don’t need to do what doctors commit to; doctors have the Hippocratic oath.

I think for most businesses that are worth a lot—whether the people are trying to be ethical or not—if they have value it means they’re providing value in some way or another. Now, of course there’re some like casinos, which you could say are basically doing nothing good. But with Facebook, I feel like it’s another version of inventing the telephone. It’s a revolutionary communication and I think that’s a really valuable thing. Steve Jobs never gave any money to charity, but he created Apple. He created tens of thousands of jobs and he gave us all this great new revolution in the phone industry. So I think it’s hard to find too many really valuable companies that are not doing something valuable. Again, it’s difficult to define what’s ethical and what’s not. But then on the other side we talk about being childish. I think someone who’s a billionaire who doesn’t give very much and doesn’t do anything philanthropic; I think that’s a bit childish. It’s just not thinking that hard about it, it’s not that logical. And he’s worth 40 billion. So I think him giving away 99 percent of his money is a very adult thing. It’s him understanding that at the point of having 400 million, or four billion, or 40 billion, his happiness is not going to change, his family’s fortune is not going to be changed. So at that point he’ll get a lot more out of trying to really fix a bunch of things. I think it usually works itself out. Worst-case scenario, someone starts a business with no ethical parameters and they make a ton of money and they save all of it. Well, then what? What are they doing? Someone just has it under the mattress. In this case it’s not saved, it’s invested. It’s making the economy more robust. And a robust economy helps all kinds of ethical things. So I don’t really criticise someone who just wants to start something big and they’re being selfish. I think if they’re creating a valuable thing, they’re creating value. I think it’s okay.

I have one last question. I think about your life calendar, your graph of a 90-year life in dots. It’s not much time that we have. So what do you want to do with yours? Do you feel like “Wait But Why” and this journey you’re on of articulating all these big ideas and engaging with this big audience, is that, like, act two?

I don’t know. I think 50-year-old Tim is so evolved from where I am now that he’s practically a different person. It’s hard to know what that person’s going to care about. I learned my lesson early from doing the wrong things and I’m just trying to do things that are fun. And right now this is really fun for me, and if it stays that way I’ll keep doing it. But if it stops being fun I’ll try to think of a different way to do it or do something entirely different. So I really don’t know the answer to that question. But I can say that it felt like I was wasting those years before when I was doing something that on paper looked great but wasn’t really exciting. I felt like I had one foot out the door of my own life, like I wasn’t being present in my own life. And now I don’t. I’m like, “Okay! This is good! These years are being used well and I’ll figure out the later years later,” as opposed to before when I said, “Something’s got to change. Is it this year? Is it next year? When is it going to change?”

And why was that for you? Who in your past influenced you to go for it? Was there that?

Honestly I don’t think there’s any one person. It’s just what lit me up, creating something. Whether it was writing something, writing a piece of music that I thought was really good, or writing a blog post that I thought was really good. That lit me up much more than hiring the right employees and designing a system to carry out a service and do that really well. Some people are the opposite. Some people love building a company, love working with employees. But for me, the euphoria of working really hard—it’s really hard at the time—and finishing something and feeling like, “This is really good” and then being able to have people experience it, that’s what I want to spend my time doing. At least right now. Again, maybe when I’m 50 I’ll be sick of that and my impulse will have totally changed. Sometimes what makes you tick changes.

No one tells you about that when you’re younger. But, like, you’re going to want to evolve. And shit’s going to change.

That would take a lot of pressure off young people who think they have to figure out exactly what they want. It’s like, 10 years from now you’ll be a different person. That person will figure out their life. That’s not your problem. You figure out what you want to spend the next few years doing. People feel paralysed, I think, coming out of college worry about making a decision. They think, Who do I want to be in the world? It’s like firstly,

You’re still the scientist no matter what you’re doing. You’re not the experiment. And secondly, you can change. People always change. And thirdly, you don’t even know what you’re going to want, so you can’t even predict what’s going to be right for the person you’ll become. So there’re so many reasons to not think of it as, “I need to make my decision and I’m going to be…” Fifty years ago people wondered, Should I be a teacher? Should I be a doctor? Should I be a lawyer? Should I be an accountant? And that was who they were. They were putting on the hat for the rest of their lives. And I just don’t think that’s how the world works right now.