"Why Greatness Cannot Be Planned" — Ev Williams

I've always found you to be a very deep thinker you think a lot and you choose your words carefully and ask a lot of good questions and I'm always curious

about the inputs what you feed yourself in terms of information and I've read that you're fond of a few books this may have changed because this is from 2016 but Zen in the-art of Motorcycle

Maintenance Robert piig the effective executive by Peter Ducker I don't know if you would still stand by those but I'm curious if so why those books and if there are any

others that you would add to that list where'd you get that list that is New York Times uh EV Williams favorite books.

HTML yeah I probably wouldn't pick those um now it's been a while um I'm not an executive anymore so I I mean that's not

as useful Zen the art Mar psycle manten is great but I will mention one B very related to the conversation which is have you read why greatness cannot be planned no great title though why

greatness cannot be planned I've recommend this to 100 people love this book it's the the subtitle is the myth of the

objective and the premise is is by a guy named Ken Stanley and another guy um who were AI researchers and the way it starts out is they this is early AI research Ken when

worked at open AI later they were building Bots and the example they talk about is trying to build a a a robot to go

through a maze and and how they you know tried to program all kinds of smart algorithms into it and then they found that the most effective strategy was just try something

new and they go on from that and extrapolate this idea that if you are trying to do something that hasn't been done before you know we're taught from

birth and from school and everywhere is like set your goal make a plan to get to the plan persevere go through that and the premise of the book is that works if

it's something that's been done a lot and that's formulaic and you can you can set a goal to run a marathon and you can you know download a training regime and you can go run the marathon and probably

get you can't do that to invent the computer or Twitter or like do you know create amazing art you it's just you can't plot it and to

the extent you try to plot it you shoot yourself in the foot because you cut off the possibilities that that lay before you and I read this book when I was

running medium my last company and it it had a great effect on me because I felt this deep sense of relief because my entire business and stter career I I've

been deeply driven to create things I saw like companies in particular product as a creative process you know it's like writing a book or painting a painting is

like you have to figure it out as you go you don't have it fully baked in your head from day one but what I've seen happen a million times and happen to me is you have this intuition you kind of

know what it is you start develop it you're like oh it's this not that let's try this not that and and you feel your way into what's the best first version

of it if you're lucky and good enough that that first version you know meets with some success in the world then you know in at least in the tech World employees and investors and

business people come in it's like okay where are we going next what's the plan what's the road map how we going to make the numbers go up and it just doesn't it

doesn't work to very far it it works like a little bit to get that next stage but it doesn't work to really innovate it doesn't work and so you have to be comfortable with the ambiguity of not

knowing where you're going to go anyway this book is is good and it makes this points very short it also talks about Evolution a lot and how like at the most

creative force in the world is clearly nature and like it has no plan it just tries [ __ ] trial and

error yeah all right taking notes that's going to be one of my next trees