Tim Urban

August 28, 2017

Normally being stranded in gridlock traffic during torrential rain sucks. The only time it doesn’t, is when you’re stuck with one of your favorite authors. This is the backdrop for my interview with Tim Urban, author of Wait But Why. We covered many topics that he writes about in his blog and also delved into his in-person experiences with Mark Zuckerberg, Sheryl Sandberg & Elon Musk. Tim was engaging, funny & forthcoming in this one-of-a-kind experience.

I had just finished my morning interview with Seth Godin and began to drive off from Hastings-on-Hudson with my photographer/co-pilots Adeline and Erik. We were still buzzing from the experience of meeting with the wizard when my focus quickly turned to my midday interview with the raddest blogger on the internet: Tim Urban (yes, he’s going to be uncomfortable when he reads that, but it’s a genuine statement). The plan was to meet up with Tim in Brooklyn and conduct the interview in the back seat of Erik’s car as we drove him to Manhattan …

‘Wait, a car interview!? Keep is classy, Dean!’ Yes, unconventional, but it was a solution I came up with since our schedules were not intersecting. Tim’s ‘Manager of Many Things,’ Alicia, told me he had to go from Brooklyn to SoHo around noon, so I suggested this plan which would help him get there while we conduct the interview at the same time. Win-Win!

For those of you who are unfamiliar with Tim Urban, he is the author of WaitButWhy.com; a long-form blog that has a fanatical readership base. As the world typically strives to make things shorter, Tim writes very long and in-depth posts on a variety of subjects such as the future, time, artificial intelligence, social awkwardness & current events. Did I mention his posts were lengthy? I’ve had to cancel weekend plans because I got sucked into the beginning of one of his book-sized posts and did not want to put it down (true story). Tim’s genius is in taking extremely complicated subject matter and delivering it with his casual writing style. It’s laced with profanity, stick figures he draws to show situations and smart comedy. I’ve yet to read another blog that is such a treasure-trove of content that fascinates and entertains in perfect balance.

I’ve got to put one more important thing into context for you: Tim is no lucky schlub who just happened to write a blog that caught fire. For starters, he graduated from Harvard University. Before starting his blog, he had already co-founded another successful company: ArborBridge. His TED talk on ‘Procrastination’ has over 20 million views online AND he recently surpassed the 1/2 million subscriber mark for WaitBuyWhy’s e-newsletter. The dude is brilliant and none of these things were by accident. Ok, now let’s go back to the day of our interview …

We arrived in Brooklyn around 11 am and knew we would be waiting for Tim to finish up a podcast he was doing with the New York Times. The madness which transpired over the next two hours I’m going to have to put in chronological bullet point form otherwise this would turn into a Wait But Why Jr. post:

  • Torrential downpours, with flash flood warnings that didn’t stop for hours.
  • Adeline and I jumped out of the car to go on foot to find the building Tim was in.
  • New York City traffic was in gridlock. Literally.
  • We met up with Tim, but then couldn’t communicate with Erik (who had the car).
  • GPS on our phones wasn’t working (due to weather & time of day, I’m guessing)
  • We were briefly detained by police because I led Tim and Adeline past a restricted area. My bad!
  • After 15 minutes of uncertainty, I visually identified a Mobil gas station to meet Erik.
  • Tim exclaimed, “I feel like I’m in an adventure movie” as we ran through the rain to the car.

... So now that we’ve framed this unorthodox interview, let’s step inside the vehicle at the exact moment we jumped in.

[Setting: Tim, myself, and Adeline are all drenched from running in the rain, but are relieved to be in the car. We start driving towards Manhattan where we will drop Tim off at his lunch meeting. I knew it would take a while due to the conditions outside, but couldn’t imagine what would happen over the next hour. After several minutes of getting our bearings and drying off, we began the interview …]

Dean: Okay, Tim, thank you. A pre-planned interview in the back of a moving vehicle. I call this New York efficiency. Have you done this before? 

Tim: I have not done this before, no. This is new. 

Dean: Well, fortunately, we were not detained earlier after going past a barrier that we shouldn’t have and somehow we made it through the rain, so I appreciate it. 

Tim: [laughs] This is actually a lot more exciting than my normal interviews. 

Dean: Okay, good. We’re off to a good start then. So, I describe Wait But Why as the blog of an obsessive researcher that likes humor, A.I., numbers, and the future. How do you describe what you do and write about to people that haven’t read it yet?

Tim: I basically say I write long-form … thorough, long, illustrated articles, I guess … blog posts … sometimes they’re like short books on kind of anything I’m interested in. Sometimes that’s tech and the future, sometimes that’s human psychology of some kind, sometimes it’s just something that I’m observing in society. It ranges, but that’s kind of the best vague explanation that I can give. 

Dean: By the way, I love the frequently asked questions section there. 

Tim: Yeah, that was the first thing I did on the site and it needs to be updated so badly and I just haven’t gotten around to it, so it’s just living there. 

Dean: It’s hilarious because it’s kind of this inner-head dialogue between somebody and themselves. 

Tim: I got very angry at the hypothetical reader as I wrote it. 

Dean: Okay, because it’s certainly like an existential thought, too. Like we’re a blog, no, we’re a website…

Tim: It’s still confusing. 

Dean: I think it’s awesome. So, if you had to pick one post that encapsulates Wait But Why, which post would that be?

Tim: Um, maybe, the post on artificial intelligence. It’s a two-parter. That, I would say, encapsulates the kind of long form explainer that I do. And I need to give a second answer because there’s really a whole other kind of post that has nothing to do with that. I think the post on procrastination sums up the kind of inner-psychology explorations that I do. The two of those together kind of represent the site. 

Dean: You mentioned the A.I. post. I think this is the same post, but what I was telling you earlier when we were running through the rain is that it’s fitting that I’m interviewing you right after Seth because he mentioned it in one of his workshops. And he mentioned the die-progress unit, I remember writing it down, and it really resonated with me … so I wanted to know … you have Seth quoting you, you have Elon Musk’s team calling you, you have some big eyeballs on you in stature and in number now, has this changed the way that you approach writing?

I published it at 5 am on the night of the election …

Tim: It’s enhanced my perfectionism in that it’s even harder for me to get posts out because I just want them to be everything I want them to be, but I would say that I’ve tried hard to not change the general vibe or the general idea of what I’m trying to do. Because to me, that’s what I like doing. That’s why I started this. I think it’s held pretty firm, plus we’ve gotten longer for sure. But I think that’s a natural progression of my own based on just wanting to kind of outdo what I’ve done, which leads to more thorough deep dives and I think that sometimes, I need to reign that back because I’ve gotten out of control with that and you’re eventually writing full-length books on a blog, which is pretty much what I’m doing and I need to kind of pull that back because books are made for books and a blog is good for things that are not quite as long, I think. But yeah, I don’t think it’s evolved too much because of some of the more intimidating eyeballs that are on it now. 

Dean: I wanted to ask you about the election post. I remember reading it very soon after it was posted. Was that the first time you really felt the masses?

Tim: It wasn’t the first time, but it was definitely one of the major times when I felt that something that I had scribbled through the night … I published it at 5 am on the night of the election … and yeah, over one million people read it the next day. I don’t think that what I wrote was quite ready for prime time. I still believe in the general ideas of it, but for something that’s so sensitive, I’d like to have a little more time to bring in the nuance that that kind of topic warrants. That said, sometimes good stuff just comes out wrong when you’re emotional and you just write it, so I don’t know. 

Dean: I saw that you have over 500,000 subscribers to your e-newsletter. You must have some haters and trolls out there. How do you handle them? Do you have a policy for that?

“Why do you swear so much in your posts?”

Tim: There’s definitely always going to be … Honestly, I try to appeal to like 1 out of 1,000 people. If you hit 1 out of 1,000 people, that’s potentially a 7 million person audience of people that really resonate with exactly what you’re doing, so I’m always focusing on those 7 million people. So if it’s a stadium of 50,000 people, I’m focusing on 50 people that really click best with what I’m doing. When you focus on those people, there’s going to be some of the other 999 people that very much do not resonate with what you’re doing. They don’t like the tone, they don’t like the language you’re using, they don’t like the fact that there are these amateur drawings, they don’t like the topics, they don’t like how long it is, they don’t like how short it is, they don’t like a lot of stuff, right? And most of those people will read it and say, “This isn’t for me,” and they leave. But of course, there’s always some people who read it and say, “I’m angry that he’s doing something that I don’t like and I’m going to try to tell him to change that thing.” With those people, I don’t take it that seriously because if someone’s like, “I don’t like what you’re doing,” I’m like of course you don’t, 99% of people don’t. That’s the point. It’s made for a very small number of people. I guess that’s the long answer. If someone writes something and I think that they’re misunderstanding something, then I’ll respond. Or if I did something inaccurate, then I always want to fix that and I will respond. If they’re just responding and being like, “Why do you swear so much in your posts, you shouldn’t do that,” what’s the point of responding? Where am I going to get with them? It’s actually a Seth Godin line … “This isn’t for everyone”. It’s the easiest way to counter that, which makes them realize that the fact that this isn’t for you doesn’t mean that there’s a problem with the thing, it’s not meant to be for everyone and you’re part of the group that it’s not for. I’ll read a lot of comments, but if I read one that seems like it’s a big rant, I’ll kind of usually not give too much attention to it. And if it’s someone that I do think that I’m writing for and they have feedback, then I think it’s super valuable, so it kind of depends on that. 

Dean: How did you get started [with the blog]? What was the initial vision that got it going?

Tim: It was kind of like I’d be on the Facebook newsfeed and there would be so many short, really short, big headlines, lists, click bait headlines, and big headings in the post, and those can be great if you’re in the right mood, but it seemed like there should be a little variety. There should be some of that and there should also be some things that are much more thorough, or in depth, or serious, or whatever it is. Or like instead of just political rants, it should be something that’s really digging into what both sides think and there wasn’t much like that. I found that whenever there was something that was really good that was a little more thorough or clearly high quality where someone spent a long time on it, I found that often, those things went viral. So I said, okay, there’s a hunger for something more here. The conventional wisdom is that no one will read long things on the internet, but my observations and my own personal taste told me otherwise so that was kind of the idea. What if I started something where instead of spending three hours on a blog post like I used to, what if with this new thing I spend 60 hours on a blog post? 

Dean: Is that the average amount you spend nowadays? 

Tim: Honestly, nowadays it’s even more. The last post, the post on ‘Neuralink’, I kind of tried to estimate and I think it took about 400 hours to write that. But again, it’s a 38,000-word post. It’s kind of how long that will always take me. It was just the hypothesis or the classic example that so many times, people start a business because it’s something that they wish existed, so I was kind of like I wish people would forward me really good explainers on stuff or really deep dives, visual … and so I decided to make that. 

Dean: You and Andrew Finn founded [the company] ArborBridge and then you also co-founded Wait But Why. So, two successful ventures. What makes the partnership work? Is there anything that you can share that has helped make the partnership work?

‘I don’t like the way you made me look in that meeting’

Tim: Partnerships are complicated. It’s like a marriage, a business marriage. [laughs] Look, if you can find a good partner, it’s awesome. You have someone to talk about stuff with, you can expand what you’re good at because two people have a wider skill set, but a lot of partnerships aren’t great and I don’t think that those are good for business, or good for the people involved, or good for the friendships involved. First of all, one kind of easy metric or easy litmus test is if there is person A and person B and they’re partnering, would two person As or two person Bs as partners be a better team than person A plus person B? And if AA or BB is a better team, then it’s not a good partnership. You should rather have you and the other person than two of you. If that’s not true, you should find another partner or work alone. You have to be enhancing what each other is doing or filling in the gaps in some way. Secondly, you have to be able to communicate well. There’s going to be times when you just disagree or you’re mad at each other and if you just don’t know how to talk that stuff out, you will inevitably end up building resentment. It’s really just like a relationship and it will turn into loud fights or it will turn into a major falling out with people not speaking anymore. So you have to be able to kind of err not just like ‘I disagree with you about that business decision’, but like ‘I don’t like the way you made me look in that meeting’, or you’re not picking up my calls enough and you need to be better about that. You have to be able to get into the really interpersonal stuff. In my case, we can because I’ve known him since we were five years old and we’re good friends. 

Dean: Wow, so you’re lifelong friends. 

Tim: Yeah, we’ve been disagreeing and yelling at each other for like 30 years now. For us, it’s not a big stretch to be very honest business partners with each other. And I don’t think you need to be best friends with someone, but just like you don’t need to know your significant other for 20 years before you start dating them, you’re looking for someone that is a good fit that you can communicate with. I think it’s important that that aspect is there along with that skill set aspect. 

Dean: So, being a company founder myself, who also has a blog, I wanted to know how do you get it all done without drowning? Today, it’s more literal, but just in general.

Alicia can say no to stuff before I even see it otherwise I’ll be so tempted to do everything.

Tim: I spent a lot of years doing like three things and not being satisfied with how I was doing any of them because I was spreading myself thin and I felt like I was drowning, and like I wasn’t moving forward with anything. It was not a good system for me. I think some people might be able to handle it, but for me it was bad. When I started Wait But Why, I said I was going to do one thing only. That was a good step towards drowning less and feeling more productive at the same time. The hard part of that is closing doors when you know there’s potential here and I’m going to close that … it’s really, really hard especially for a perfectionist personality, but doing so was critically important for me to be able to feel fulfilled and like I’m doing something valuable. That’s one thing. Then as Wait But Why starts to pick up, you start drowning again. I do feel like I’m drowning currently, but I’ve done two things to try and mitigate that. One is that I hired someone awesome, Alicia, who just does a lot of different kinds of things for Wait But Why. She does a ton of stuff that clears stuff off my plate and she wears a lot of hats, so that was really helpful. I can’t believe I waited as long as I did to hire someone. The second thing is just getting good at saying no. It’s like closing doors again and new doors will try to open with your new thing and sometimes, something sounds fun or potentially like a good opportunity or it sounds like something you’ve really always wanted to do or whatever, but it just doesn’t fit with your schedule and you know it’s going to eat into the thing that you care about. I think it’s really important, and it helps to have a person by the way. Alicia can say no to stuff before I even see it otherwise I’ll be so tempted to do everything. So basically, by starting Wait But Why, I said no to my other ventures. And then within Wait But Why, constantly saying no to new things … sometimes it’s a no within my own head. I’ll think this would totally be such a cool project to take on and I was like, no, that’s not what I’m doing right now, so just limiting the overextension of yourself that way is just really important. That said, I still feel like I’m drowning, like I’m taking on too much. 

Dean: It’s interesting that you talk about ‘saying no’. I mentor college students and one thing I told them is that right now, your job is to ‘say yes’. Just say yes because later in life, responsibilities and life will catch up and ‘no’ is the key, but early on, you’ve got to say yes. 

Tim: I totally agree. It’s really interesting, there’s totally a balance where like when you’re in college, you want to dip your toe into a bunch of different things. You’re not trying to do something great yet and that’s the key. You’re not trying to climb up a mountain yet, you’re at the bottom of a mountain and you want to walk up a few feet of 50 different mountains and see what they look like so that you can figure out what mountain you do want to invest a ton of time in. Once you’ve gone through that process … which actually might take your whole 20s! I have friends that are 35 that are just figuring out what mountain that they want to be on and sometimes they could have figured that out earlier if they hadn’t just jumped up the first mountain they saw and they kind of feel like they could have saved that eight years or whatever. Once you do figure out a mountain that you are satisfied with and you’re pumped about it, then in order to climb that mountain when there’s going to be a lot of other people trying to climb that mountain, then you have to put the other mountains out of your mind for awhile at least and say no to everything. That moment when you pick your mountain is when you switch, but I totally agree with the say yes advice for college students. 

Dean: I’ve got a question about the instant gratification monkey [the fictitious character who is in everyone’s head and side tracks productive behavior]. By the way, as soon as I mentioned to my wife who I was interviewing, she said, “Oh, it’s the guy with that instant gratification monkey!”. In one of your posts, you say that you have 60 tabs open at one time [when researching]. Would you say that’s some form of unleashing the instant gratification monkey to do the research in a specific domain? 

So it’s when they’re having a conflict, usually, the monkey is not right.

Tim: Here’s what I would say to that. The dark playground isn’t just when you’re clicking around Reddit or something. The dark playground is anytime you’re doing something that the adult in your head is saying, “Why are we doing this right now. This doesn’t make sense. This is not a good plan. You’re going to regret this later.” If you’re doing it anyway, you’re in the dark playground. Is the place where you’re self-loathing. You know you shouldn’t be there, but there’s some other force in you that’s just keeping you there. Now, sometimes that’s leisure activities when you know you’re not supposed to be doing them, sometimes it’s the wrong kind of work. Now, I call the other characters the Rational Decision Maker (that’s the adult) … when the adult and the monkey are in agreement, like when you’re sitting down to a good meal with friends, they’re both happy. The adult says great, this is a great thing to be doing and the monkey says I’m having fun. When you’ve finished work and you’re going to go and have leisure time that you enjoy, both people are happy. The adult doesn’t want you to have no fun, the adult says good, this is the time to have fun. So it’s when they’re having a conflict, usually, the monkey is not right. Usually in the conflict, it’s because it doesn’t make sense to be doing it and it’s self-defeating. Research is a good example because at the beginning of research … well, it depends because sometimes the research is hard and the monkey doesn’t want to do it … but when the research is really interesting, the monkey can get addicted to learning about something, the Rational Decision Maker is happy because we’re researching for this post, and then at some point, the adult says let’s move here, I think we’ve done enough, let’s start outlining the stuff, and let’s get onto the post so this doesn’t take forever and the monkey says that sounds hard, unpleasant, I don’t want to outline, I want to keep learning. And as the perfectionist creature that’s also like we’ve learned, we’ve read like 30 of these tabs and there’s 20 more open, we can’t just leave them (even though I just opened them haphazardly in the first place). So these other very compulsive, primitive parts of me are basically forcing me to spend like three times longer on research than I need to and the adult is screaming, this is enough, you don’t need this extra stuff, time is more important here, you’re going to regret this. Then because I do all the research because the monkey wins that battle all the time, now the perfectionist can’t handle not putting all of the research in the post, and the adult is saying just cut stuff, it doesn’t matter, you’re making the post worse by putting all of this stuff in. It’s a real like nightmare head I’ve got going on here. So I guess that’s how I would say it. When it’s unhealthy, when the research now doesn’t make sense, that’s when the monkey alone is doing this and it’s not the Rational Decision Maker. 

Dean: Anyone reading this that hasn’t seen your blog is going to read it now because they’re going to go ‘what are they talking about with this monkey and decision maker?’ So go read the blog! For the record, I concur that Elon Musk is the raddest man on earth. I actually asserted last week that he’s either from the future or he has access to some future person, that’s my assertion. 

Tim: It would make a lot of sense, right? He came from 2150 and he was like, okay …

Dean: … ‘I know it’s possible, I may not know how to do that one thing, but I know we can, so you people and you people’ … 

Tim: If an entrepreneur from today went back to 1870, you’d say I’m going to dive into light bulbs and we’re going to do this because I know this is possible and then we’re going to start working on a combustion engine because I know that’s possible … I feel like that’s kind of what he’s like.

Dean: Okay, so we agree that he’s the raddest man on earth. Who is the second most rad person on earth that you’ve met and why? 

…. around the same time to meet Sheryl Sandberg, which was the most intimidated I’ve been by someone …

Tim: Let’s see. Well, I had a chance to interview Mark Zuckerberg recently and I don’t know if I would anoint him number two, but that guy is for real. I mean, he is working on not just Facebook, not just that Facebook is the leading company in VR now because they bought Oculus and they’re doing more than anyone, but they’re trying to put satellites in the stratosphere to bring internet to rural areas, the Chan Zuckerberg Foundation is trying to cure every disease by the end of the century. They’re working on brain machine interfaces just like Elon is that can relate to VR. He’s a big thinker and talking to him, it reminded me of talking to Elon about how this guy thinks super big and he’s only 33 now, 32, something like that, so I wouldn’t be surprised if he ends up being as impactful as Elon by the end. I don’t think people realized that about him 5 or 6 years ago when they thought of him as just a guy who runs a social media site. So, I think that he’s underrated and he’s a good contender, maybe. But there’s a lot of people who I’m very impressed by who I’ve been lucky enough to meet while writing this blog, so it’s a hard question. I had a chance around the same time to meet Sheryl Sandberg, which was the most intimidated I’ve been by someone because I just wanted to impress her and I was not doing a very good job of it because I was trying too hard. She’s very little and you’re like wow, imagine such an amazing and powerful person … I pictured her being like seven feet tall … so it was just weird to talk to people you idolize and then try to talk to them like an equal because that’s how you’re going to get someone, but it’s hard and you’re in your own head when you’re meeting with these people for the first time. I think once you have a few touches and you’ve been able to meet with people more … in the beginning with Elon, I was a mess. I was a total mess, but now I’ve had a chance to talk with him a bunch of times and I find that it’s become very easy. I can kind of be myself, I know the vibe, and it’s not a problem. 

[At this point we take a 4-minute break. The rain is coming down extremely heavy and I’m unsure of where we are or how much time we have left for the interview. Tim is texting with his lunch meeting to try to update them on our commute left (which seems to be stuck at a fixed amount of time). Concurrently, we’re looking for subway stops close by that Tim could switch to. Little did we know right now, but the subway was also grinding to a halt due to the bad weather and ‘train traffic’. We then start the interview back up … ]

Dean: In your most recent post, you mention that, if there were two camps, you’re on the optimistic side of the future of artificial intelligence … what gives you optimism?

Tim: I go back and forth with whether I’m really on the optimistic side or not, but I think that if I want to figure out the future, I just look at the past and extrapolate forward. There’s been a lot of times where we’ve been scared of what’s coming and then it turns out to not be the end of the world and it turns out to make life better. That said, sometimes I go into another zone where I think well yeah because those weren’t as big a deal as A.I. and not anywhere close and this is different and can’t be compared in the same way. So, I go back and forth with how I feel about it, but I think there’s a good chance that we will figure this out in a way that we can’t understand now; we can’t understand how we can do this safely get because we don’t get what A.I. will be like when it gets to be human level intelligence, but I just think that when it’s a species thinking about something and that they can’t visualize the good future, you just assume it must be bad. But, you know, we might surprise ourselves and come up with a way to do it totally safe. I just have faith that we’ll figure it out somehow. That’s not really a scientific answer, but that’s kind of where I end up landing usually. 

Dean: I have some questions from social media. I posted earlier that I was meeting with you so I have some rapid-fire questions for you. So Tom wanted to know, what’s the one value you hold closest?

Tim: Oh man, um, this is such a cliche answer, but I feel like it’s authenticity. For your own sake … [Dean: so, not trying too hard?] Well, no, sometimes you do have to try hard because there are parts of your brain that don’t want you to be authentic, they want you to try to fit in at all costs. You override your own kind of authentic self all the time for the sake of fitting in, or getting ahead, or out of fear, or insecurity … all these things. It’s very hard to be authentic, you have to override a lot of your own brain to do so and I think that figuring out how to do so is the key to everything. I think if you’ve really, really figuring that out, you’ve figuring a lot of other stuff out. Your relationships are better, you pick a better career for yourself, you end up more successful, more likable, with more meaningful interactions and experiences, fewer regrets. If you mess something up being yourself, you’re going to regret that a lot less than when you overrode yourself and then something went wrong. The answer is authenticity, but it’s maybe not the exact kind of thinking that I think people would have when they think about that answer. 

Dean: Mike wanted to know, who do you go to for advice?

Tim: I have a lot of people that I look up to in areas that can help here … so my agent, Richard Pine, is a wise guy. I definitely look up to him. I always ask Adam Grant questions, he’s a good friend and he has been doing this a lot longer than I have, or at least a little longer than I have … this whole writing thing, speaking, and all that. I often just ask my girlfriend who knows me really well, who knows Wait Buy Why really well and often has kind of a clear view of what’s happening when I just can’t see because I’m too in it. And then a handful of other friends. I mean, good friends are good people to ask because they know you and they get it, but they’re not as emotionally involved. So yeah, some combo of that and some professionals I know who are in the same fields. 

Dean: So Rajiv wanted to know about the future of A.I., say that we don’t have to work as much. How will adult humans define themselves and their purpose if not through work and vocation? How can we start to have these conversations to orient the next generation?

You’re a complex, evolving, shape-shifting, creature …

Tim: I think it’s probably good anyway to not fully identify with work because work should be like an experiment that you’re working on, but you’re the scientist. You’re not the experiment. And that’s always been the case. Especially more recently when people change careers a lot … I think it’s dangerous to think of yourself as the experiment because that makes failing terrifying and changing careers is really a whole thing and it’s hard and you have to explain it to everyone and you feel like you have to change your identity. I think it’s a healthy change regardless of what the future brings, I think we should do it anyway. We should talk to kids like they’re the scientists behind their work and the work is the experiment they’re doing in the lab. You are not defined by what you’re doing. You’re a complex, evolving, shape-shifting, creature that takes on different things throughout life and the things you take on and you want to take on will evolve as you go. 

Dean: The final question I have for you is one that I always like to ask at the end. If you could put your humility aside and kind of look at yourself in third person, what is your secret to being outrageously remarkable?

Tim: I’m definitely uncomfortable with that term for myself, but I think I’ve had the most success when I’ve been able to follow my own observations and my own judgments and the hunches I have, even though they don’t really seem to make that much sense by conventional wisdom. Sometimes I’ve done the other thing and I’ve let conventional wisdom or fear drive me and that has not turned out as well for me by a long shot, so I think it’s the times when I’ve been able to really just trust myself that things have actually moved in a positive direction. I think that’s probably the case for a lot of people, especially in the creative arts world, but also entrepreneurship. Often, we have a lot of good, creative, original ideas in us that we don’t let out because of conventional wisdom, which usually lags 10, 15, or 30 years behind reality … It usually conflicts with that. When it conflicts with that, we usually ignore our own reasoning and we defer to conventional wisdom, which I think is a pretty big mistake. I think it goes back to the authenticity thing. I think all the forces in you that are trying to get you to fit in or not trust yourself made sense in the tribal days when … if conventional wisdom says don’t eat that berry, you should follow that. Life changes so quickly that conventional wisdom lags behind and it’s not good to trust it anymore. 

Thank you, Tim. I’m ready to be more authentic in my writing.


Special thanks to my photographer Adeline Ramos at You Look Lovely Photography, along with her husband Erik, were my co-pilots for the day! It wouldn’t have been the same without them. 

Check out Tim’s blog Wait But Why hereThis post was PART 2 of a 2 part series. Part 1 is Seth Godin.

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