Transcript Tim Urban – Wait But Why

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making a new post every sometimes with

my guest Tim urban Tim it’s a pleasure

welcome to hxb

thank you for having me Tim I I find

your your writing incredible man I

relate with it so much from your

procrastination post to the Elon Musk’s

series seems like you’ve written about

everything that there is to write about

it seems like everything that you’re

writing about goes viral and what’s

what’s the secret well I think it’s once

you have a decent-sized audience that is

aware of what you’re doing and is into

it then then I think it’s it’s it’s

about kind of delighting that audience

and and you you can you know you what

you do can spread throughout that

audience each time you do it and so

that’s gonna seem like a very successful

post each time because the audience is

of a certain size but I would still say

actually most things don’t really go

viral in the traditional sense you know

viral to me is when it’s all over the

place and it’s reaching all kinds of

people who have never heard of of what

you’re doing and and that’s not really

what I’m aiming to do anymore at the

beginning I definitely was because I was

trying to get attention for the new

thing we were doing and trying to pick

topics that would that would really

make a splash hand up in that way yeah

well let’s well let’s back up a little

bit I mean it wait but why is this sort

of content I mean what do you what do

you call it now is it a blog still yeah

I call it a blog it’s a terrible word it

is I call myself a blogger which is a

terrible work but yeah it’s it’s I’m

writing long-form articles on my own

site so whatever that is in the world I

I guess that’s them that’s that’s a blog

but it’s almost like you have this

magical decoder ring where you know you

you punch in these numbers and you click

viral and it just it explodes so where

did you know where did you start

where were the humble beginnings that

you know no one ever hears about yeah

well I think about 2005 to 2011 I have

another blog that was much more of a

kind of odd normal blog the articles

were much shorter they weren’t

Illustrated and they were kind of uh

sometimes about my day or about things

that annoyed me and that I did that for

six years and I wrote 300 blog posts and

there’s almost no chance you’ve ever

heard of it because nothing ever went

viral on that it was uh it was read by a

you know small group of people that

really liked it and we had fun and I

really liked it writing it but but so

that that’s that’s where I you know

learned how to write blog posts and kind

of found my voice and learned about the

relationship with readers and my own

process for kind of coming up with ideas

and writing you know getting in the

habit of writing things down when I

would have an observation during the day

and so I kind of learned all the the

important kind of skills then for

writing a blog and then a couple years

after I I stopped writing that I decided

with Andrew my business partner we have

this other business that we were running

together to try to start kind of two

how to do the blog again but to really

like do it right you know take

everything I learned and and try to try

to kind of go at it you know in a really

serious way

you know we saw all kinds of content all

over the Facebook newsfeed and and

things like that on Twitter and just

just articles that were okay

that you know we’re usually very short

no big headlines lists a stock photos

and sometimes you know they make you

laugh sometimes they’d be great

but you know very often they’d be okay

and and once in a while there’d be

something really good and you see it on

your newsfeed or somewhere else like

four times or five times and then

someone would email it to you and then

and then it would appear one of those

newsletters you know and and you kind of

we kind of thought about and said you

know when something when someone really

puts everything they have into an

article and it’s like this really great

thing it seems to make the rounds and so

even though there’s kind of a notion of

content you know out there then we’re

kind of inside of the there’s not a

notion of really good content and so

that was kind of the hypothesis and so

start to wait but why in 2013 so it’s

been three years yeah it’s been about

three years let’s explore the the

process I mean you you mentioned that

let’s let’s explore the process for you

I mean how does how does that begin I

mean you’d you take notes during the day

about what you kind of what annoys you

and he said well so in the in the old

blog I was doing things you know 19

things I don’t understand and 25 things

that annoy me and it’s actually annoying

because this was this is one of the

things that annoy me now one of the

things that annoys me is that I was

doing these lists like it’s you know

number of things that something you know

fifteen things that something that was a

format that I was I thought was all you

know clever and fresh and I really liked

it and it was fun to write in that

format and people liked to read it this

was 2005 2006 2007

and in the time since then it has become

the most overdone overused format now

and someone sees an article that some

know something things that something I

think everyone just kind of thinks this

is gonna be cheap low quality and

someone is you know just trying to get

clicks and it’s actually a shame because

because those those are really fun

articles to write now I feel like it’s

you know you don’t get the benefit of

the doubt them anymore but that’s an

aside so back then it was just yeah I

mean I would think of something I would

look at the dishwasher and think what

the hell goes on in there how possibly

does everything in there get clean like

what what is happening in there and and

out and and the detergent I put in this

little thing close it how does it go

from this little thing into all those

water and not get used up right away I

mean I was just very confusing so that

would be an example I would have that

thought I would just write it down and

then when it was and then I would time

to do a blog post and I would go kind of

say okay well there’s but there’s a the

list of things that don’t understand has

now grown again since the last time I

emptied it out for a blog post it’s now

up to you know 19 I always had 19 things

I don’t understand so I would take them

and I would write a new post and then

I’d start every time I didn’t understand

something I would I would put it in that

list until I hit 19 again then I would

write a new one so that was my process

with the old blog and but now with wait

but why you know that the topics are

much broader and so now it’s it’s still

still put stuff like that others if I

have an observation I think I bet you

other people think this too I bet no one

else knows how to with a dishwasher

happen how it works but but no one talks

about I’ll just write it down but also

I’ll write down I keep hearing about

Bitcoin and I no idea how that works or

I’ll think wow there’s so many people in

unhappy marriages what the hell is going

on there so I’ll go write it down and

and you just get if you just get in that

habit you end up with this incredibly

long list of thoughts and ideas and

observations and insights and sometimes

this is a great conversation you have at


with someone and and notes this one of

these really just really interesting

conversations and you can I will finish

that and I’ll think oh wow there’s so

many interesting things that came up

just now and I’ll just write them down

and and that becomes your topic list or

that becomes kind of your your your your

source material to then build upon I

mean I really want to break this down I

want to demystify kind of deconstruct

this process what is the first thing

that you do in the morning when you wake

up so I’ve actually gotten better I used

to just take my laptop right down to the

bed and start like doing stuff emails

which is a terrible thing to do it would

then be 2 or 3 hours later and I would

still be doing that Haiti myself so I’ve

gotten better about not only had the

laptop in the bedroom anymore ever so

now I I’m much more in control I get up

and I will turn on well it depends if

I’m if I’m in a if I’m trying to there’s

certain days when I’m in the process of

brainstorming or outlining a post and if

that’s the case then the morning is

precious brain time because your brain

is in a very specific very important

state so like the first 20 minutes 30

minutes when you wake up it’s this raw

state and and you know I actually I

actually intentionally try to think

about the topic and the brainstorm and

the puzzle I’m trying to put together

the night before like right before I go

to bed and you know that kind of I think

you know that you simply assert you know

if you if you’re playing a game

incessantly late at night and then

you’ll dream about it it’s that kind of

thing or your your your you know

thinking about one kind of one person a

lot you’ll dream about them so because

your brain takes whatever it takes a

signal from your consciousness about

what should we be trying to figure out

in our sleep okay got it and then it

works on that while you sleep so I’ll

think about whatever the post is I’m

trying to do and kind of signal to my

brain this is what we need to work on

tonight and then when I wake up in the

morning if that’s why it’s so bad to

pick the laptop up because it just

shatters it’s just you just you waste

the the insights that they’re right

there waiting for you and you just

distract yourself with other things so

just I just tried to get up and get in

the shower and just start thinking and

it’s it’s usually amazing how many new

thoughts come in the same way if you

want to memorize something you know you

do it before you go to bed and then in

the morning when you wake up it’s it’s

solidified so so that that’s in those

days but most days I’m not in that zone

I mean they’re just you know writing a

post or I’m you know in between coasts

or whatever in those days I’ll turn on

an audiobook or a podcast then I’m you

know into and I’ll just turn it on my

speaker and just kind of carry the

speaker around with me as I do stuff

which will be showering and I’m not

great about breakfast but I’ll try to

like have something so that it’s taking

any days off I haven’t had a schedule

now which I’m trying to stick on because

I used to take no days off and I was

just always kind of in some state of

either procrastinating from working or

working and and so I and I I decided

that I needed to kind of force myself to

take time off even on those weeks when I

felt like I have not been productive

enough we just don’t you know that’s

when you’ll just get into the trap of

you’ll just never take a day off because

you so I now say Saturday’s is a day off

and I’ll intentionally schedule you know

hang out with a friend at 2:30 which is

like being the worst thing I could do if

I wanted to be productive that day

because when I wake up that’s looming

ahead so I’ll never get anything done

before that and then by the time I’m

back it’s like 6:30 and now so I’ll do

those things and purpose to just say

wake up Saturday no you know what would

nothing productive needs to happen today

and what do I want to do so I’ll do that

and then I also try not often often not

successfully but I try to just at 9:00


just stop working and and you know then

I can start looking forward to you know

actually I’m gonna oh I 9:00 p.m. I can

do this at 9:00 I’ll do this tonight

instead of thinking off at some point I

need to do this I’m like I can even do

it tonight and I know this sounds crazy

too it gives it just like 9:00 is not

very early time you’re not so

to be working that late but for me it’s

it’s I will just continue all the way

until I go to sleep and it’s not because

I’m such a workaholic it’s much more

because if I know I have all that time I

just won’t be productive till pretty

late in the day I’ll just I’ll just dick

around basically and you know on and off

until 5:00 or 6:00 and then I’ll say god

I can’t believe I haven’t done anything

today and then I’ll just work till 2:00

in the morning

and I think I’ve been working on kind of

setting aside these no work blocks which

I think forces me to treat the work time

more seriously

yeah I’ve been I’ve been doing the same

thing – the dicking around I’ve been

really just I’m a workaholic so for you

I mean is there something that you feel

determines that you’ve had a successful

writing day it’s so black and white for

me which is something again I’d really

don’t want to be the case because it’s

not a very healthy way to be but for me

it’s it’s often that I I feel I’m like

really unhappy with my work day and then

I just I I got a little stuff done only

and the stuff I got done was not the

important stuff it was that urgent stuff

that doesn’t actually that’s not what

matters and or I I’m in one of those

zones where I I’m in a really good zone

and I’ll like get 14 hours of you know

of blog posts to work done and then and

then I’m happy about that but then my

the rest you know all these texts built

up in my phone people being like you

know I’m just being non-responsive and

I’m it’s really like you know the answer

somewhere in between there and so a

truly successful day for me which I

which happened more is you know III

would get up and I would you know around

10 a.m. I finished all the morning stuff

and I sit down and I do emails and

meetings and other things like that

until about 1:00

I try to schedule things in that window

10:00 to 1:00 and then at 1 o’clock I

shut all that stuff down and I dive into

creating whatever I’m working on

creating at that time the blog post or

maybe a video

whatever it is and I work on that until

about 9:00 and then I stop feeling great

about the digs I just got a ton of stuff

done and I’m caught up with my other

stuff from the morning and now I can

enjoy some time off and then because of

that because then I give myself two

three or four hours of leisure time I

feel fine going to bed at 12:00 or 1:00

which for me is early because uh if I

don’t do that what happens is I’ll kind

of not let myself do anything leisurely

until you know it’s like 12:00 or 1:00

time to go to bed and then it’s like

some part of me is like some part of my

brain the leisure part is like no we’re

getting our time we’re not doing nothing

I’m gonna now go see what the sports

scores are the day and I’m gonna read

this article and before you know it it’s

2:45 and now I’ve like kind of destroyed

my next day this is something that I

find pretty remarkable about your

writing which which I really enjoy is

that you have this sort of it’s almost

this sort of sardonic sinfully mocking

it’s the almost dark style I mean is

that me am i projecting do you or do you

feel that way or it’s humor ‘fl you have

this sense of humor that that relates

through your posts but I mean do you do

you feel like you’re mocking things in a

way well I think there’s a lot of

there’s a lot of things in life in the

world to me that kind of just are

begging to be made fun of and there’s

kind of a lot of things about humans and

I’m the specimen number one for myself

that are to be made fun of so I’m

usually writing from a place of I’ve

been dealing with my own like human

flaws all week so I’m already in kind of

that mood and then I’m also whatever I’m

writing about either I’ve been reading a

bunch of experts or watching interviews

or I’ve been just brainstorming why

people are or do a certain thing and

there’s so much ridiculousness and all

of that usually that that I do get into

I can I can get into it a tone where I’m

where I am I just want to point that out

either because it’s funny to point it

out or because I I want people to be

thinking about it more but um but I

think there’s also I think kind of

beneath that kind of it like that

that’s within like a well of kind of

excited optimism as well because I’m

also kind of like really like really I

really like life and I really like

people even like people I don’t like

like I like the concept of people and I

just a few manatee you know and I’m

excited about the future and so so III

think there’s um yeah III I hope I hope

that it’s not like you know cynical I I

like it being kind of mocking without

being really negative and cynical

because that’s not really Who I am so I

hope it you know I wanted to reflect

that yeah yeah I mean I’ve got a few

more questions on your writing style

that I promise we’ll move on I doubt

this is fun for you but I feel like

people might want to know you know kind

of what but what drives you and how how

you’ve you know sort of developed this

this style that reaches so many people

when you are creating a post is there a

process in which you sort of visualize

where the post is going organically

piece by piece or how much how much of

the story arc have you kind of just

decided on already before you begin

writing yeah so for me basically all of

it that’s a really important thing for

me because I need to when I start

writing the first word I need to kind of

be ahead of the reader I need to be in

control I need to kind of know the plan

and I want to be I want to be in the

mode where I feel like I’m this this

storyteller are talking to people who

don’t know the story yet and and it

would be a terrible feeling for me to

start a story with a bunch of people and

and not and just making it up as I go I

just would be much worse I would be much

worse of telling the story I wouldn’t

have the confidence of a storyteller who

knows where he’s going I wouldn’t be

able to foreshadow I wouldn’t be able to

to kind of to set the mood and the way I

want and bring the mood to where I want

and all those things and so for me if I

wrote if I you know some people I think

thrive in a very different way then just

start writing and think

happen and then they go revise later I

hate that because if I just start

writing out know where I’m going by the

time I figure out where I’m going now I

have to go back and fix the tone and

everything cuz it’s not what I wanted it

to be so for me I would say more than

50% sometimes like even more than like

70% of the total time between when I say

okay here’s the topic of the next post

let me get started – when I’m published

to post more than half at that time

happens before I write the first work

because there’s always a big you know

sometimes it’s just a post like you said

about you know procrastination though

that kind of those kind of posts are how

to take a life-partner those posts are

just mostly me thinking about what I

think about stuff and thinking about

what I’ve observed in other people and

what I’ve gone through myself so I have

a lot of brainstorming time and a lot of

thinking time or sometimes it’s a post

about something in tech or science or

something like that

history in which case I’m going to be

just doing a ton of reading and research

and interview watching but either way

that process is the beginning where I’m

just gathering information and just kind

of putting it in a pile in a in a

document just gathering gathering

gathering without any discernment yet

for what what should or should not make

the post or what the actual structure is

and then I go through the next process

the next stage stage to kind of which to

me is the hardest part the least fun

part and the part where I definitely am

tempted to procrastinate away from it

the most which is I’m currently as we

speak by the way in a full

procrastination zone from one of those

from that some of the second stage I’ve

done the fun part I have all the ideas

I’m excited about the post and now I

have to do the actual kind of homework

which is taking that pile deciding what

the post actually is what’s gonna get

what’s gonna make it into the post what

I’m gonna leave for some other post some

time what the structure is of the post

which can be 200 different structures

it’s not like an obvious structure if

you look at a bunch of my posts or any

bloggers or you know there’s often

you’ll see my posts have many different

structures and so you have to kind of

decide that and it’s torture because I

decide on one I think well this other

one you know I don’t like it it’s not

quite you know there could what if

there’s something more creative and more

creative structure and then and then you

know actually figuring out there are the

outline the arc you know and you know

what is it two three main parts or is it

a list of ten things or is it one big

story and am I telling this like I’m

inventing a character and telling it

through them it’s like a fiction is like

a seems like a fiction story or am i me

am I am I just being me the author that

might just be myself and talking to the

readers like earnestly you know and so

you have to kind of make all those

decisions because if I don’t make the

decisions like that then they um they

often just get made kind of by accident

I don’t think that ends up as good as

good a post so that that’s that’s what

takes up you know ton of the time but

that’s remarkable I love that

I mean is there when you look at other

blog other blog writers blog posters I

mean are there certain weaknesses that

you see that that other people are kind

of making mistakes that you see that you

notice well it’s hard I mean I’m still

still trying to figure out kind of how

to do my own thing enough that I don’t

think I’m quite ready to kind of

critique others that much but one but a

couple things I will say that I just

noticed both my my old blog writing and

some blogs I see today is I think people

are sometimes they think they know they

they have their journalist voice on you

know or something like that they they

have a certain tone on that’s not really

human it’s journalist II and that I just

feel like we’re not in that that era

anymore like I don’t think that if you

look at what’s really poppin online now

it’s it’s often like a person being a

person in in writing versus you know

someone you know the okay the ultimate

example is like you know 20 years ago

like I’ve been front page New York Times

article that’s not a human at all that

is a very specific voice which is it is

you know super formal and it’s not

you’re not supposed to see any semblance

of personality you know supposed to see

no you’re not supposed to know anything

about whoever the human writing it is

they are completely hit right and then

you go to something like today something

like my blog or many others I think

comes you know James clear I think of

Mark Manson I think of Allie Brosh and

hyperbole and a half I think you know

these people they are in a hundred

percent of a human it’s it’s good when

from 0% to 100% now not everyone some

people want to have a certain kind of

voice that’s not necessarily them and

that’s art and that’s fine but I think a

lot of people are trying to go for you

know connecting with an audience

building a following and they try to and

and they they they’re they I think they

need to do a better job often of just

getting to that you know 90 or 100

percent human level and getting farther

and farther because people are scared

they think you know I’m a writer

III have to be people will think I’m a

better writer if I asked like a writer

it’s a no act like yourself you can

still have a writing style that’s not

exactly how you speak but I just think

that that to me is something I think you

know modern-day writers should be

thinking where do you see your readers

kind of going

is there any specific topic or John rrah

that you see your readers going to or

it’s like are they magnetized by your

relationship posts or well what I would

say is um you know because I’ve written

about a bunch of different things I

would say there’s there’s a there are

some readers who are just really similar

to me in which case they might like a

lot of the different things I read

written about because the things I’ve

chosen to write about are things that I

as a person happen to find interesting

and you know fun enough to dive into for

a couple weeks and some people are

really similar to me and if I’m writing

about artificial intelligence they’re

like oh that’s that I love that topic

that’s so interesting and then if I’m

writing about relationships they’re like

oh that’s kind of how I think about

relationships you know and so those

people are course arose right down the

middle way Pillai readers those are

gonna be the people who like it the most

but then there’s some people who they

really like posts like artificial

intelligence and they like posts about

other technology and Tesla and and they

want to hear about the Fermi paradox

kind of these heady kind of sciency tech

techie type things and those people they

know they they all you know if I get an

email from one of them they’ll I can

tell you know it’s not it’s not

surprising when they tell my favorite

poster this this and this I’m saying

you’re right cuz you’re you like that

kind of post and if I write about

relationships they might read it but

they might think oh well III thought

this was like an awesome tech blog what

are you doing and then other people who

got you know who first found the blog

because of procrastination or because I

talked about why you shouldn’t care what

other people think of you or you know

why people act a certain way on Facebook

it’s kind of human psychology kind of

poking fun at life but also analyzing

you know how we can be better people

somehow right those people I think again

some of them also happen to really or be

into the to the tech topics but then I

think some of those people are kind of

like you know they they are sad when

it’s when it’s a post that’s not about

um you know about something with

humanity so I think um I think it just

depends I think because when you’re

gonna when you’re writing a very broad

blog you have the advantage of you’re

gonna attract you know there’s gonna be

some posts on wait but why for for a

huge group of people you know what

they’re doing a huge group of people

where at least one post appeals to them

well if I were just writing about sports

you know now that you know now there’s

fewer people that can find something on

the site they like so but that’s the

advantage the disadvantage is you know

if I were just writing about sports

there’s the people who like the site

they like everything on the site because

this is their thing and and the

disadvantage for me is that you know

there’s I matter what I write there’s

some maple Y readers who are

disappointed that that’s the topic

because that’s not what they’re

interested in so you know I don’t know I

just think it’s it’s it’s a trade-off

but you’ve built this massive following

I mean it’s huge within within three

years you’ve built I mean it’s it’s a

business I mean you’ve you create a

business out of this blogging idea and

and people love it I mean it I mean you

guys are getting what like at least a

million reader readers a month right

yeah and I mean so that must put a lot

of pressure on you as well right oh yeah

I mean it’s it’s um

uh it’s it’s really mind-blowing if I

think too hard about like what the

numbers look the actual how many people

that actually is because that’s just not

humans are not programmed to like to

absorb that kind of information and to

know to not freak out so if I think too

hard about it yeah then I become

overcome with pressure and perfectionism

where I’m like you know that I can’t put

anything you know I even just you know

I’ll send you know every post comes

along with an email because I’ll ever

you know I don’t use the email a story

much other than to send out new posts

but when I do I’ll often put a little

note at the top just a little friendly

note saying something that we’re working

on or a new thing that I want to point

them to or just to kind of update people

on what the plan is for the next month

whatever it is and so I just write that

read it over once and send it let me

think about it like as if I were sending

an email to a friend and then once in a

while like oh it’ll hit me as I’m doing

it how many people are gonna I’m sending

that note and then I become paralyzed

and I can’t do it I just can’t it’s just

I’ll read it ten times I get incredibly

self-conscious that you doubt everything

so that’s a it’s not a good creative

place to be and if you think too hard so

I actually end but the truth is you end

up your your brain kind of it you know

is happily not conscious of the truth

with with the readership and I think for

me it feels very similar you know it’s

different but it doesn’t feel that

different having the million people or

so visiting a month now versus having a

thousand people visiting my old blog it

just you you know my brains kind of

adjust in the same way and even though I

know it’s a very different situation it

kind of feels the same like I was very

gratified when I wrote something I

thought was good on the old thing and I

in it and I feel similarly now do you

feel like do you feel like you’re

adjusting your writing style because of

how large your user base is no well so

that yeah so that’s that’s interesting

because there’s some ways this is I I

definitely it definitely affects me in

some ways it’s good one way is that I

know that if I write anything about

Tech history politics anything and

there’s something about it that’s not

correct or that’s like only talking

about one side there’s going to be 15

absolute experts in that thing in the

comments section saying how wrong I am

which makes me lose credibility to

everybody because all the people who

didn’t realize that when they read it

because they’re not experts then they

read those experts saying and I think oh

I can’t trust this guy right exactly

yeah so now I’m like and likewise if I

ever even accidentally like 1/8

plagiarized something by just kind of

doing a diagram and the similar way to

someone else the way someone else did I

mean I’m gonna I’m gonna

people are gonna absolutely call me out

on that publicly in front of everyone so

it keeps me I have to be I had to have a

lot of um has to be high standards for

my fur for fur for accuracy and for

originality and that’s a good thing that

keeps me like you know just tip-top

shape as a writer in that regard I can’t

get lazy I can’t get sneaky I can’t get

you know whatever on the the time when

it can be negative is if you know I I’m

someone who I think a lot of writers I

think a lot of creative people are sense

like somewhat sensitive and they want to

be liked they like to be liked like you

know people talk about Obama like that

like that’s one of his his problems as

the president is he doesn’t like to not

be like I think there’s a lot of people

who have that quality and it can and it

can be problematic in certain

circumstances so I think for me like

just knowing that a lot of the people

who do read the blog like it and like me

it’s like I don’t it’s like I then you

can quickly stop take that side of you

that’s like edgier that can be kind of a

dick that can kind of um kind of uh just

make fun of a certain kind of person and

a pretty harsh but funny way you can you

can quickly kind of put that part of you

away and say no no no sorry yeah this is

just you know I just I can’t you can’t I

can’t say that about and I don’t think

that’s not you know Mike because then

what happens is your taste starts to be

disappointed by it like what you’re

putting out like your like my taste

might think oh that’s so funny when

someone else wouldn’t some other writer

write something but then I find myself

you know what if I had that thought I’d

be like I don’t know and it’s like no I

mean if you got to still stick with your

tastes even if some people are gonna

hate it and especially some of the

people who already really like you who

don’t know I always I have such an

affection and fondness for anyone who

likes to blog and I just don’t want to

like hurt anyone’s feelings who really

likes what I’m doing but you can’t let

that affect your tone and your and make

you worse so I think that that’s

something you know that’s that can be

dangerous yeah yeah I understand


you know there’s I’m a huge stand-up

comedy nerd I like to study stuff and

and there’s there’s this sort of saying

it they call it the forever box and

inside the forever box you can say

anything literally anything that you

want and people just love will love it

like you get into this rapport with your

audience and they just love what you’re

saying and doing so they laugh

automatically Elon Musk it this is this

is such a huge thing just because I mean

if I feel like when Eli Elan musk enters

a room like harps play angels sing it’s

like there’s this there’s there is

something happening with you on must

that you know should be noted and he he

invited you to interview him and write a

series on him how did that work out yeah

yeah that was that was like the coolest

definitely coolest thing that’s happened

in my life in my life so far so yeah I

mean I think he’s a pretty amazing

person and the more I’ve learned about

him I’ve learned a ton about him and

what he’s done in his his life in the

last year and I’ve been more impressed

so I feel like you know it made me

realize that you know you assume someone

who gets talked about so much and prays

so much is probably overrated a little

bit and actually I kind of think he’s I

kinda think he’s underrated I don’t

think people

get yet you know how incredible what

he’s doing is and so so you know I was a

I was already you know a pretty big fan

and yeah he kind of started and it was a

2015 like early 2015

he started tweeting tweeting out wait

but why posts like he did it three

different times and and they know each

time was just completely like a

mind-blowing day of my life and you know

and it started to hit me like okay this

dude’s aware of the blog like officially

like he’s just and so so that that was

awesome and then and then and then his

uh his assistant you know reached out

and you know and actually you know said

he would like to give him the phone one

day and just talk about maybe some doing

some writing about his industries if

that’s something you might be interested

in and they were very polite as if they

were kind of like intruding on my time

she’s hilarious

um and and so yeah so that happened and

yeah I and suddenly I’m on the phone

with him and really not you know not not

what I saw coming plan other than kind

of I think he thought that you know my

very long form very thorough style was

was very was it was it was a good match

for his industries and and I think

that’s probably correct because what

he’s doing with Tesla what he’s doing

with SpaceX um those things are so

complex there’s so much background you

need to know to understand why those

things matter so much and why we should

be as the public should be in great

support of both of those missions you

really need to educate people on those

things for them to understand and I know

that cuz I didn’t quite get it when I

first started this whole thing and then

I started reading and said all oh man

like this stuff is you know yeah this is

really really important for so many

reasons that people don’t get so I think

that was the idea he said you know this

guy will write a really thorough posts

on this and that’s what we need because

I don’t have time for a three-hour

interview which is what you know he

would need in order to to explain

everything his interviews are these

little soundbites in 20 minutes and they

asked the same circus questions and

people ask him about you know PayPal and

there’s just no one no one really gives

you know he doesn’t have the chance and

and his companies don’t really have a

mechanism to educate so I think that was

the reason behind it and then yeah and

then I spent six months writing you know

four posts that would that would be like

a together a pretty long book yeah

that’s amazing it I mean it really does

show I mean you were invited to a TED

talk I mean it really does show the

success of wait but why just because of

all these things I mean it seems like

you guys have captured lightning in a

bottle here yeah well I I always have

the feeling like it’s it’s um it could

it could go away and this is not like

you know it’s it’s not like we have

these you know customers or the count’s

and we have like you know contracts with

with things like you know business when

you feel like okay we’ve like built

something it’s solid like you know blog

blog you can be popular and then they

can go away so it’s really very a lot of

a lot of hum gratitude every day that

this is because again I spent six years

as a blogger without this happening so

really grateful when it is happening and

just you know trying to enjoy it while

it lasts and hope that it’s a bit of

sticks and that I can keep putting

things out that uh that kind of warrant

this kind of readership that’s good man

I really really respect the the

gratitude party I think that’s a that’s

a huge deal so Tim let’s let’s get back

into your process a little bit I mean

when you feel stuck within an idea is

there any certain thing that you go to

where you feel like it invigorates you

or gives you creativity we sometimes I

will literally just have to like reset

if I’m just in the bad zone I’ll go for

a walk I’ll take a shower I’ll go to

sleep I’ll change rooms but honestly is

mostly when I’m stuck it’s because

I’m avoiding you know it’s like I’ll be

working and I’ll kind of hit a bump

that’s something that I’m like oh wait

that’s a problem that’s not gonna that

that won’t reconcile with the other plan

I have here yeah something has to change

and then and then what I do is then

I will start doing something else

because that’s pretty hard what I just

described and actually I don’t want to

deal with that right at this exact

moment so I’m gonna deal with something

else and what happens is the bump grows

even though the bump hasn’t changed in

size in my head the bump becomes a

little bit of a hill and then it becomes

a mountain and then it becomes Mount

Everest as days as you know suddenly 1 2

3 4 days have passed and I have I just

got away from my process for 4 days

because of a bump that I could have

gotten over in 10 minutes if I just

spent like 10 focused minutes working on

it so often when I’m having a problem

it’s because I’m just avoiding and if

the thing that solves it is when I just

confront the confront Mount Everest work

on it for a second realize it’s just

remember that it’s just a bomba fix the

bump and then they get all excited and

then I keep going but again that that

process that that between when I leave

the bump to when I get back that can

take them that can really eat up a bunch

of days when I’m doing all of this

important not important but urgent stuff

you know emails and you know meetings

and other things that I that are just

not the real thing I’m trying to do so

to me it’s often the solution is just

closed down everything else on my

computer and just sit there and look at

it and think and get back into it and

sometimes 10 minutes later I’m rolling

again that’s so so interesting to the

whole creative process and and really

you know immersing yourself putting

yourself completely into you know

writing and and doing it full-time the

way that you’re doing it you know is is

there is there a post of yours on the

site that is kind of a favorite I mean

my personal favorite type posts are just

type of post that I would like to read

the most and that are just masais it’s

the for me ironically it’s some of the

posts that have no writing at all I did

a post called

putting time in perspective I’m looking

at that one right now yeah so that post

to me was the most fun to do ever

because writing is hard and and and and

but just you know finding facts about

timelines and making this little simple

graphic and getting excited about all

when this is done this is gonna be such

a great graphic you know I’m so excited

to own this just to be able to like

reference it and I was and I’m like or

in and and I was learning a lot so to me

I had a great time making that and

that’s like this very few post I go back

to myself too because if I start

rereading for a second I all I do is

well all I can think is all the things I

want to change and so I I don’t usually

do that but with with that post I go

there all the time just to actually get

information or just to look at it

because I think it’s so interesting

just because history so interesting in

this spans of time are so incredible and

and that to me that that graphic really

kind of just makes you know clarifies

that in my head so that to me is like my

favorite or you know I don’t know

certain you know just a funny answer

because that’s again one of the few that

doesn’t have my own voice in it and now

it’s it’s good an honest answer I loved

the novelty aspect that you kind of

continue and you you know you’re

sticking with the things that that that

interest you and you know what you said

earlier about retaining the sense of

sort of humanity and the people who are

writing to be liked versus actually just

being their authentic you know their

themselves and and I think there’s I

think in today’s society when you know

everything is measured by a page view or

a click or something it it’s it’s so

important that you know you you do have

this sense of overwhelming honesty and

and the moment that you don’t at the

moment that you

kind of playing around and the moment

that a person senses that you’re that

you’ve just created this post so that

they can click on it the sooner that

they’re gone and and I mean you just

don’t ever see them again

well I used to be the case I think that

this we are now living IIIi think this

is becoming more and more obvious in an

era of people like authenticity being

the most important thing people don’t

want fancy graphics you know high budget

you know corporate graphics you know on

something they don’t want journalists

voices they they they don’t want you

know cheesy ads and marketing messages

that are obvious they just people and

and they’re starting to really really

hate clickbait and and it’s one of these

things where you know you can just see

it like louis c.k is such a product you

know he of course you know he this is

like the Louis CK era and almost you

know this guy is so honest so authentic

he you know and and and of course he’s

the most popular stand-up comedian in

the world and I just think there’s that

you know Jon Stewart was so you know

himself that’s why he was so ragingly

popular that this you know the young

current young generation like they’d

rather you be mediocre and unprepared

but raw and yourself then being you know

something that is that the bullshitting

them for whatever reason and what

happens is when you when you’re in that

era people develop a really really

fine-tuned radar that I don’t

think they had 30 years ago just wasn’t

isn’t I don’t think you know I don’t

think that it ought anticipate any

professionality or other things mattered

but so III think that that’s just

something that you know it doesn’t

matter how is a matter how good you are

at being authentic hard and it’s hard to

continue to be that way

because it’s kind of scary to just be

yourself but that’s what people want

they want real people yeah and I think

you know what you said earlier about how

as you develop this sort of following

and as it increases the

sure of that the idea of you know okay

there’s going to be you know ten

thousand a hundred thousand people

reading this holy that blows my


I mean um so it it does kind of change

it’s kind of like the Schrodinger’s kind

of cat you know is it a lot versus dead

and once I got it you know you you find

out but you changed the outcome alright

is there any certain thing that you feel

like you’ve learned about people through

through the success of the blog well

it’s a little along the lines of what I

just said I think that I think that at

least at least my readers I mean they

they want substance and they want

authenticity and I think people want to

learn like I think a lot of people have

a craving to learn I mean it’s as crazy

structure of our society where you’re

supposed to learn until 22 you know or

whatever around 22 and then and then

that then you’ve learned stuff and now

you go and you do stuff and that’s just

so outrageous given that you know you

can be the best the most genius

scientists of all time people like

Fineman and Einstein and Newton they are

they have quote after quote after quote

about how they know nothing and how they

they there’s an ocean of stuff they’ll

never know so there’s just manure nning

is so invigorating and it’s so I just I

I think it can it can it once you know

learning suddenly makes makes it makes

that it makes more learning about that

topic suddenly super fun and it makes it

really fun to talk about it suddenly and

it feels really great and it’s also just

really interesting if it’s taught in an

interesting way I think also a lot of us

brand learning as boring because

learning in school is boring so I think

that people want to learn a lot more

than I think sometimes they get credit

for and I think um people want

authenticity I think again so many

people are kind of scared to just kind

of be themselves scared to curse scared


to kind of to kind of just be kind of

casual yeah you know that we’re not no

one’s wearing suits to work anymore like

it’s just a different time it’s just so

it’s missing it’s okay to be a human

publicly but the whole normal human is

fine it’s like fine you know and people

are gonna like you for that and the

paradigm has shifted and you know I

think people expect different things now

we are so inundated with information and

if if you watch television

I mean spares or so but I mean if you

subject yourself for that to that media

is constantly pushing all this

information at us all the time so I

think I think just to remain relatively

sane I think we have to kind of limit

and still be very selective of what we

decide to feed our our brains our minds

yeah I think there’s just I I I’m

already just overwhelm the open you know

my podcasts happen I see how many

multiples hours of great content out

though that I’ll never have time for how

many audiobooks I have them I think just

looking at dad my options in the morning

there’s there’s no way and so and

there’s so much great like amazing

amazing stuff to take in that that it’s

insane how much time I wasted on on

taking in bad stuff it’s crazy

but I think we all do still it’s just

out of habit or out of you know I don’t

know like we know it’s like you know

it’s almost like to take in something

really good I have to commit that’s the

activity I’m gonna read this great book

right now and and I ended up taking in

more content not when I’ve decided to

take in content but when I’ve decided to

work and I procrastinating and I’m just

for a minute I’m gonna read this stupid

thing and then that turns into 40

minutes and now that thing that kind of

crappy content consumption took up 40

minutes while I spent zero minutes that

day reading something really great

that’s sitting in my bag that I’m dying

to read so you know I think that um that

yeah I just think we should have a meter

on reminding ourselves how much great

stuff there is every time we’re reading

something or consuming something or

watching some stupid video that is not

really enriching us or delighting us

yeah so to I mean we’re

running out of time here I’ve got you

know look I really want to drive this

this home and I and I I really want the

listeners the people who are listening

to kind of get to know you better as a

person so you know is is there any

single one thing that you would I mean

how old are you now 34 so is there any

single one thing that you would go back

and tell your 21 year old self oh so

many things but I think the main thing

is just the thing that jumps out at me

is you know as far as career goes at

least I would tell myself that the world

is mostly built you know in Mozilla

people who didn’t really know what they

were doing and that and then and that

everything I’ve gotten you know is

seeing the inside of a company or the

the way someone has made and an album or

something else that you think is this

amazing process you could never touch

it’s actually just kind of like flawed

people and if you think you’re really

good at something you’re probably better

at it than the people who were doing it

and they’re famous for it you probably

are here’s a good chance just because

they’re you know just because they’re

doing it they’re famous for it does not

mean they’re in this it’s not it’s not

like sports you know it’s not like I

think I’m pretty good at basketball but

I could never be Michael Jordan right

you could never be Michael Jordan but

that people have applied that logic to a

lot of other things art and business

they look at you know someone who’s

older company for a billion dollars they

look at someone who is a number one

best-selling author and they they say

well that’s the same Fame level that’s

the same they’re the top point all one

percent just like Michael Jordan so I

couldn’t be them and that’s not true

it’s not like basketball at all there’s

a good chance person selling their

company for a billion dollars is not any

better at business than you and I’m

really if you think you’re if you think

you’re good you think not great but you

think you’re a smart person who has a

knack for this thing that is a that

means a lot if you think you’re a smart

person who has a knack for something you

you probably can beat the point

1% and really what the main thing that’s

in your way is not the superhuman Kalen

because it’s not even that doesn’t exist

what the main thing that’s in your way

is that you’re not going to go for it

you’re not going to charge ahead for ten

years and try to do it because you think

it’s a it’s a hopeless quest like trying

to become Michael Jordan so and but I

got daunted by that for I didn’t start

something like wait but why with all my

might I did all these creative projects

on the side yeah 10 years because I

didn’t have the guts to just do it


because it felt like a though what are

the chances that’s a one in a thousand

it’s just completely false and if I

could go back I would have told fall

head you know headfirst into creative

endeavors I thought I was good at full

time with my full-time job starting

right after college and I 39 years

instead I feel like you should drop the

mic after that little statement a

beautiful man love that so crucial and

and I agree a hundred percent I feel

like we’re so misled and I mean our the

structure in which we kind of create

learning and distribute knowledge is so

flawed and the direction in which people

are going to chase what they think are

their dreams and then realized aren’t

and then end up you know quitting their

corporate jobs to go and refine

themselves again end up on pages like

yours or we’re listening to podcasts

like mine what’s next for you Tim what

is I mean what is a what – what’s your

what’s your next goal what’s your next

thing what are you doing next yeah so

right now I just my main challenge in

life is to try to be as productive with

writing as I was in the first two years

you know and right now because there’s

you know I it’s I I I’m just trying to

right now do wait but why well for a

while and just you know continue to do

this thing but really really be writing

a lot so that’s my first my first goal

is just in the near future just write a

bunch of really good blog posts very

excited about that right now

and I feel like I haven’t gotten enough

out recently so that’s one thing and the

second thing is I think I’m you know

looking at bigger kind of a bigger

project either either a book or a like a

video series or something that to kind

of continue to push myself out of my

comfort zone and challenge myself with

something like totally new but still

with the same but still under you know

still with wait the why and still with

the same kind of trying to get the same

kind of messages out but just trying to

do it in a medium that I’m not

comfortable with because I think that’s

this is still a good time to be doing

that so I would say that’s those are the

main things on my mind

cool a team working where can people

find your blog your work um everything

is just at weight but wide calm that’s

basically everything that exists for me

currently that matters is there so and

then you know I always tell people that

the best way to the best way to kind of

stay in touch like you know if you if

you like it it’s just do the email

subscription because that’s just know

for myself I end up really keeping up

with things that they’re gonna email me

every time there’s a new post and the

ones when they don’t even if I like it I

just forget about it for a long period

of time so Tim thank you so much for

your time and I love what you’re doing

love the message thank you so much for

for being here

yeah thanks for having me on this is the

human experience we will see you guys

next week thank you guys so much for



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