“Half of the reason I decided to do this book was to learn… what does it take to write a book? Not only the process that you go through but what is the personal journey I am going to have to go through to become the person that can write this book? And it turned out to be as expected very difficult, lots of ups and downs…”
Buster Benson is incurably curious, and luckily for the rest of the world, he’s also generous and creative in sharing his journey. In this conversation we talk about the power of writing as a daily practice, how he had to learn to draw after deciding he wanted an illustrated book, and of course why learning to disagree well expands and improves your world, the topic of his book Why Are We Yelling? The Art of Productive Disagreement.
Buster’s site: https://busterbenson.com/
Buster on Twitter: https://twitter.com/buster
Buster on Letter.Wiki: https://letter.wiki/BusterBenson/conversations
The ‘How to write a book very slowly’ timeline: https://busterbenson.com/book/timeline/
Alison on Twitter: https://twitter.com/bookstothesky
The Extraordinary Business Book Club on Facebook: https://www.facebook.com/groups/1447064765612358/
This Book Means Business – the mentorship programme: https://alisonjones.lpages.co/this-book-means-business-mentorship/
The 10-day Business Book Proposal Challenge January 2020: https://alisonjones.leadpages.co/proposal-challenge/
Alison Jones: I’m here today with Buster Benson who is an entrepreneur and a former product leader at Amazon, Twitter, Slack, and Patreon. He’s now editor of and writer for The Better Humans Publication on Medium. He’s the creator of 750words.com, which brings private journaling to a safe place on the web, I want to talk about that it sounds amazing, and developer of Fruitful Zone, an online platform facilitating healthy discourse. He’s also the author of the Cognitive Bias Cheat Sheet with over a million reads. And his new book is Why Are We Yelling? The Art of Productive Disagreement. Welcome to the show Buster, you are a Renaissance man, are you not?
Buster Benson: Thank you. Well, time will tell but yes I do have quite a few interests.
Alison Jones: Its so fascinating. What I love is that you kind of leave it all out there. You just found ways of visualising it on the web and you talk about all of your interests and it’s really fascinating. How much of this is for your benefit? And how much is for the people?
Buster Benson: It’s hopefully a mutual benefit but definitely it comes from a desire, I suppose, to get feedback from the world. Because I think I have learned early on that the best way to learn is to really let other people serve as the mirror for the ideas that I have and the thoughts, the experiments, and the projects. So, I always like putting it out there and getting feedback as quickly as possible.
Alison Jones: And did that come from, is that sort of a deep, you talk about your values and so on, is that a childhood value or is that something that’s come, I mean you’ve worked for some of the most cutting-edge sort of tech companies out there, is that a professional thing? You know, where did that come from? How did you learn that things get better?
Buster Benson: It’s interesting because often at times it plays off each other. So the interests that I have are around cognitive biases, and self improvement, and using technology to make better decisions, to improve our habits, all these things. And the process of sort of iterating in public is how you do lots of those things, and, so I don’t know, which one came first. It was sort of a chicken and egg thing but early on I think I discovered that this works. And you know I remember very early on I was part of the quantified self movement and just by posting every day on the internet before there were even blogs like how happy I was, how much sleep I had gotten, how much coffee I had drank, and then seeing if there was a correlation enough funny side effects that came from that were people sort of coming up to me at work and being like, “Wow, you didn’t get much sleep last night.”
Buster Benson: But yes. It led to a lot of entertainment I could say.
Alison Jones: That’s funny. We’ll come back to the journaling thing in a minute because I really do want to pick up on that. It’s something that’s really important to me as well but let’s talk about the book for a minute. It is one of those funny things because quite often people come to me and they’re like, well, I don’t know which book to write first, I could write 10-20, I mean you could write like a hundred books couldn’t you? Why did you settle on Why Are We Yelling?
Buster Benson: Well, yes it’s a long journey. The book originally was sort of a by-product or an outgrowth of the Cognitive Bias Cheat Sheet, which was a surprise sort of popular article I wrote in 2016. And I was approached by an editor and I said, “Wow that sounds interesting.” As I learned about biases I really became obsessed with the conversational habits that we have because that’s where our biases are the most pronounced and the most evolutionarily useful is to help us clarify our thinking, help us be heard, help us be right in an argument. And so this book became sort of the genesis or the centre point of almost all of my interests converging on conversation and disagreement as the meta skill that can really help us improve all of our other skills. So, I feel really lucky to have just stumbled upon this because having worked on it for three years you always fear that you might lose interest along the way but I have only become more interested in this idea that conversation is the skill we should all be working on.
Alison Jones: Let’s talk about the three-year thing just for a second actually, just a quick digression before we go back to the topic of the book, because one of the things that you do when you’re putting your whole life on the internet is you’ve got these wonderful timelines. And I have just shared with the group in my bootcamp actually the timeline of your book because everybody who has ever written a book will look at it and go, oh yes, I recognise the entire book about halfway through. And you’re just so open about that whole messy process and the doubt involved and the time involved, my goodness, and the people involved. Just talk us through that a little bit for people, well, I will put the link on the show notes at the end but just for the people who haven’t seen that talk us through it.
Buster Benson: Yes, I like to track things, obviously.
Alison Jones: Yes we’ve got that.
Buster Benson: Half of the reason I decided to sign up to do this book was to sort of learn the inside the black box of the publishing world, like, what does it take to write a book? Not only the process that you go through but what is the personal journey I am going to have to go through to become the person that can write this book? And it turned out to be as expected very difficult, lots of ups and downs, lots of roller coasters. There were definitely points along the journey that I felt like I failed or felt like I was on the break of the perfect book. So, capturing those ups and downs is my way of sort of tempering my expectations and allowing myself the patience to keep on going because I know that no matter how high it is or how low it gets the reverse will happen again and I don’t have to dwell too much on the current situation, just keep going. And that was my motivation.
Alison Jones: Its interesting because looking at it you can see the trajectory of the whole thing. But presumably you’re logging it in real time and you don’t get to see that trajectory, so there must be an element of faith involved in that.
Buster Benson: Absolutely. Yes, I had a couple of projects where I would track things. I used to take a picture at 8:36 every day. I was obsessed with this person Jonathan Livingston, I believe his name was, he took a Polaroid every day for 30 years up into and through his hospitalisation and eventual death. And there was this amazing art gallery exhibit like to showcase his whole work. And just like this idea that you can capture a larger narrative without actually knowing what it is. And you just do that in realtime every day, capture a dot and then after the fact you can go back and connect them all and say what did this actually mean? So, yes I know that life is going to be up and down. There’s never a fear in my heart that it’s going to be very easy and clear cut so I always know that it will show up interesting in some way.
Alison Jones: Its like the greatest vindication ever of that mantra that when you’re a writer, a good day is a good day and a bad day is material.
Buster Benson: Absolutely. Especially if you’re writing about disagreements.
Alison Jones: Yes! I mean you must have been hideously self-conscious about every conversation you had.
Buster Benson: Oh my gosh yes, yes. First of all, I am not an expert at disagreement I can’t win all my disagreements, I am in plenty of them that are unproductive. So there is always that self-conscious aspect of it like, who’s going to call me out, and point out who does this guy think he is writing a book about this when he’s so bad at it? There’s that part, but there’s also just this desire to look at this thing that is really uncomfortable in all parts of my life and it turned out that by looking at them, and working on them, and practising, my life started to change as a result of just having disagreements that I was avoiding at the time. So, it was a transformation.
Alison Jones: That is so interesting. So, tell us a little bit more about that. You’re writing this stuff, you’re researching this stuff, you’re living this stuff, I mean what did it mean for you, well, personally and professionally, I guess, to have written the book?
Buster Benson: Man, it’s a lot, a lot. A couple outwardly obvious things, when I started the book I had a full-time job, I was a project manager at Slack, and a few months in I quit my job because the timing was right, no disparagement to Slack but I was like, I’m not focused on my new book, because normally I was not ready to do that necessarily but by having the conversation with my wife, with my boss, it just became clear that this was the right thing to do. So, that was a big change and sometimes the most productive disagreements cause changes to happen that are sort of scary and that’s okay. Because often times what’s on the other side of the scary thing is something good and in that case that was true. So, that was one example of a time where just by having a disagreement it changed my life literally not necessarily in the enlightenment sense but I left my job.
Buster Benson: Now, I have been writing for a year plus. It’s definitely changed my marriage, we ended up having more in-depth conversations, we ended up starting to go to therapy to sort of facilitate these conversations. And just really diving into: what do we want out of this relationship, how do we help make those things happen, what are we going to do? So, that’s the exciting things, the world becomes bigger when you aren’t avoiding all of the disagreements.
Alison Jones: And of course as a pathological conflict avoider this is the book I need. Many of us are, and those that aren’t are often quite miserable to be around aren’t they? That’s the difficult thing. Doing conflict well is a really hard skill.
Alison Jones: One of the things I liked as well is the way that you visualised this, but, this should be no surprise knowing what you do and how you sort of map things out visually as well, but you include your own illustrations in the book and you’ve got this sort of visual path of how it goes. Which came first the illustrations or the texts or the concepts, how did that all fit together?
Buster Benson: That’s a good question because I am not naturally an artist and I had just picked up an iPad and started drawing on it when this book came about and I started thinking from the reader’s experience: What can I do to make this sort of intimidating topic less intimidating? Well, the books that I like to pick up at the bookstore are the ones that have pictures. So, I added a lot of pictures, and I also knew that by visualising disagreements it was a great tool to sort of break you out of the one-dimensional good-bad, black-white kind of situation when you can see something on two dimensions at least so I knew it would be a good tool. And that was another situation: how am I going to draw these things and how’s it going to work with the text? And I just figured it out. But I think the idea came together like, I am going to write this book and it’s going to be filled with illustrations, and then I had to learn how to draw.
Alison Jones: But you’re quite right because any book suddenly becomes much more accessible doesn’t it? And you can hold ideas in your head differently when you see them visualised, than when just simply reading text, I think we’re very visual people still.
Buster Benson: Absolutely, yes. I come back to this a lot which is very central to disagreement, which is, we have two eyes in order to see in three dimensions and in order to really think about things we have to be able to see them from different angles, process them through different parts of our brains, visual and text is one way to do it, sound is another. But in many cases bouncing it off another person, the reason you’re having a disagreement is because they see the world differently than you. If you start to think of them as a way to see the world in more dimensions, instead of as an opponent you need to squash, then suddenly you’re actually enhancing your sense of the world by seeing it through more perspectives and then the more different they are that’s an even better situation because if you can actually see the world through somebody’s eyes that are completely different than yours, wow, you’re going to see all kinds of things that you don’t see today. So, I really like the idea of processing the world through as many inputs as possible.
Alison Jones: I love that idea and its such a great reframe because its hard to be angry with somebody when you’re seeing them as your lens to a new reality.
Buster Benson: Right, yes. Loads is about reframing.
Alison Jones: It’s all about reframing, absolutely. Fantastic. Can we talk about the 750 words thing as well? When I read about this I was like, “Oh I love this so much.” So, you have been inspired by quite a lot of books and that’s one of the things I found really interesting you’ve got on your website the books that have inspired you, and its got sort of a public reading record. One of them is Julia Cameron’s The Artist’s Way. And of course you have something about Morning Pages, which, I have a bit of a love-hate relationship with, mornings are busy in our house, we have a dog, we have children, all that kind of stuff, but in another universe I am there serenely writing Morning Pages every morning. And when I do do it, it’s transformational. So, tell me how you took Julia Cameron’s vision, which is mostly about sort of creativity, isn’t it, awakening the artist within, and you did something a little bit different with it so tell me about this whole 750 words journey.
Buster Benson: Yes, well I have always been a journaller. I have always like journalling, but I have always been really paranoid about people reading my journal, and so I have always had this really strange convoluted systems for hiding my notes and my journal. In order for me to really spill my thoughts I need to be in this place where I don’t have to fear that someone’s going to read it. Even though, it’s very psychological it has nothing to actually do with what I am writing about, I stumbled across The Artist’s Way, I felt like it would be even better if I could just type this into a computer and it would automatically protect it and hide it. And it wouldn’t ever accidentally get published on my blog, or never get left on the computer that then somebody else looks at.
Buster Benson: So, all these things that went into it. The idea is really is just, if you can open up your thoughts, I think it would be sort of like meditation, where you’re trying to just be with your thoughts, and not necessarily have judgement of them, break stream of consciousness. Writing is a great way to just start spilling these conversations are unresolved in your head, concluding them, and then sort of having that feeling of, “Ah, now I can move on”. And it’s been such a great tool for me when I’m trapped in this circle of thought, I can just go there, type it all out, and end up somewhere that I couldn’t get to despite thinking about it.
Buster Benson: It turns out, that’s a useful thing for lots of people, and it was one of my few projects that, even though, I barely spent any time working on it, has continued to grow for almost 10 years.
Alison Jones: And what’s magic about 750?
Buster Benson: So, 750 came from The Artist’s Way, she advocates for three pages, and I looked up at the time, how many words are on a page? And, about 250 and multiply that by 3.
Alison Jones: You had to quantify it.
Buster Benson: Yep.
Alison Jones: That is hilarious.
Buster Benson: And getting to that is the hard part. I like the fact that it’s a little more than you would normally write, so you have to stretch yourself, and get to the real dregs of your brain, and get there, and that’s where the good stuff is.
Alison Jones: That’s so true isn’t it? I always find, with Morning Pages, the first page and a half are… you just have to get through them. But, they have nothing, and it’s when you get toward the end of the second page, you suddenly start hitting… you say the dregs, I say the gold. That’s suddenly when it really starts kicking in. And I think a lot of people just, it’s like going for a run, the first five minutes of any run are just rubbish, and a lot of people just don’t realise that you can get beyond that, it actually gets good beyond that.
Buster Benson: Like into the zone, and then the good stuff comes out.
Alison Jones: That’s right, and it’s something about sticking with it. And I guess that the great thing about a quantified target is that you know how much you’ve got to do. I’m fascinated though that you have, such a, hang up. Oh, that is just such a loaded word, but that you’re, so, that you have that hang up about people reading the journal, when you are such an open person, and you live your life… So you must put a lot of energy into where you draw that line. The stuff that’s your thinking tool, that is private, that is just for you, and the stuff that is processed enough, finished enough, to share with the world. Is that a conscious process for you?
Buster Benson: It must be, strangely, I haven’t really thought of it like that before. But you’re absolutely right. I am pretty open with everything, but there is a censor, I think the censor is around what might accidentally hurt people, so whatever processing thoughts internally, we don’t, we might have to go through these sort of pads of thoughts that might, if were just exposed to the world might hurt people. Even thought they might resolve, but at the end you’re OK. That’s really the thing that I would probably point to as the thing I would not publish about. Not that I can just work through all of my insecurities and doubts of other people publicly. I’m going to try to keep it more about myself, and less about other people.
Alison Jones: So there’s the dividing line, we’re back to the conversations, aren’t we? We’re back to the intrapersonal stuff, it’s not OK to share other people’s stories, it’s OK to process that and understand how it fits into your life, and then share that.
Buster Benson: Yes, yes, that’s a good way of putting it.
Alison Jones: That’s really interesting. And the Codex Vitae, I loved as well, I’m also a huge fan of Mr. Penumbra’s 24-hour Bookstore. Actually, I can totally get why you love that, because it’s that mix of books and technology, and encryption, and it’s just marvellous.
Buster Benson: Everything. Yes.
Alison Jones: Yes, so that Codex Vitae, you have been keeping this log since 2012, I think you said, of what you believe, and just sort of, making yourself accountable and checking in, and saying “Do I still believe this? What’s my evidence?” How strongly you believe it. There’s a lot of emoji work going on, isn’t there?
Buster Benson: Yes.
Alison Jones: As to how tentative this belief is, how strong it is, how locks into values, and so on. I mean, obviously, the Codex Vitae idea is very abstract in that book. But you’ve made it something quite, I mean, was it get help used?
Buster Benson: Yep. Yes, the idea really just being if I just write down my beliefs I can watch them change over time.
Alison Jones: Right.
Buster Benson: And we don’t really get that information, just living life through our normal experience. Because, as soon as we change our mind about something often times we, then revise our past belief as well, we think “Oh, I’ve always believed this.” When that’s not the case. Just reading your own journals is proof of this often enough. So, that was the motivation there.
Alison Jones: And, to me that seems incredibly vulnerable making, because I think I’d find it hard, even to articulate with that level of granularity. What I do believe about stuff, and there is something really powerful, about forcing yourself to say, you know this is me and this what I believe, and putting it out there. Did you have any reservations about that, or did I just seem quite natural?
Buster Benson: Oh, wow, lots of, well, not necessarily reservations, but what you said about the fact that the granularity is hard. It is so hard, that was one of the most interesting things I realised by doing this is that I don’t have beliefs about a lot of things. I have hunches, and I have, sort of, reactions to things. But, to actually know what my belief, if you circle back, you’re not going to find a belief about, you know, exactly how likely is it that aliens exist. You’re going to find more than zero less than 100%. So, part of the process of doing this, is realising how shallow most of our beliefs are, and over time the act of writing them down does help me build them. Because, I don’t want to just react to things I want to react, like be proactive from a belief. So that, when things happen in the news I would rather go back and say, “Okay, what do I really believe about this”, and then act from that stance. Rather than merely, this is bad, this is good.
Buster Benson: That has forced me to investigate and come up with details, that I can stand behind on a lot of these topics.
Alison Jones: I think that’s fascinating. Because what you’re demonstrating is something that I see a lot in people who choose to write a book. Which is, that self knowledge, that inner force in yourself, to identify what it is you believe in and how you do something, and why, and all that kind of depth of analysis that you do when you write a book. But, you’re not just doing it in the book, you’re just doing it in daily life, which is just so fascinating and really challenging actually. I think a lot of people would be like, wow. How can you not live like that? I bet it’s hard work.
Buster Benson: Yes.
Alison Jones: Really fascinating.
Buster Benson: Yes.
Alison Jones: So, I’m going to ask you, there’s so much useful stuff in here. Thank you so much for just opening up, clearly you’re quite an open person, but for just opening up so much of the thought process behind how you are, and how you show up in the world, and where the writing comes from.
Alison Jones: If somebody is listening to this, and hasn’t particularly been quantifying their life and analysing their beliefs, and so on, but they are trying to write a really good book, what would your best tip be for them?
Buster Benson: Wow, I think that is, I know can see how writing a book is a transformative process. It’s forcing you to say more about something than you probably have in yourself. And, it’s forcing you to be a person that can write the book that needs to be written. So, I really advocate for lots, and lots, of just free writing, drafts, snippets, capturing notes, trying to triangulate. Don’t force yourself down into, here’s the outline on day one. Ask a question, and then just dive into, immerse yourself in the question, and see where it leads you. And, it’s really easy to get distracted, especially if you don’t know, like myself I was a first-time writer, I don’t know if I can do this. And, so, there’s all these fears like, am I going to hit my deadline? Is this the right thing for me right now? Is this the right book?
Buster Benson: So take your time in the early stages. Before you commit to writing it, to be sure you really want to dive into that topic. And be kind to yourself in terms of missing deadlines, it’s not a deterministic process, it’s not something you can just spill out, in the same way that you can just knit a sweater. You have to find the heart of it first, and become that centre, and write from there. It might take a year, some people can write a book in three months, it’s all about timing and how much is built up. And luck. I would choose, be patient with yourself, explore the question.
Alison Jones: Just digging into that a little bit more. How do you know when the time is being well spent on opening the self up and being curious and digging in, and how do you know when you’re procrastinating?
Buster Benson: That’s a question I do not know the answer to.
Alison Jones: There’s a fine line isn’t there? I totally agree with you, I think that sense of curiosity makes just the best place to start a book from, and then free writing is the most underrated thinking tool ever. It’s just at some point, you kind of need to pull it together and go, “right, here’s what I’m writing about, and here we go.”
Buster Benson: Right, and that is always a compromise at that point. You’re really like “I’m not done yet, but I have to do something.”
Alison Jones: I could continue researching this and playing with this idea forever, and yes, you could that’s the problem. It’s such a, okay so we haven’t got an answer on that, we’re just going to leave that question out there. Good for that one, but everyone has to make their own call on that. Sorry.
Buster Benson: I will say one thing, which is, I loved the tangents, and the research rabbit holes that I would fall into. And, I actually started writing about those publicly, because, it would be so much fun to, “Oh my gosh, I just went deep down into, Linnaeus, and his tree of animals. It was so much fun.” I’m not going to use any of that, but it was really fun.
Alison Jones: What’s great is that you’ve got the ‘Piles’, the navigation on your website is nothing like I’ve ever seen before. And, you just actually create this place where you can put stuff. ‘This is stuff I don’t know what to do with it, but it’s really interesting. Isn’t it interesting stuff?’ You just stick it into ‘Piles’, it’s great. Everything has a taxonomy. And here’s another question I can’t wait to hear the answer to: I always ask people to recommend a book, it’s often a business book, it’s not always a business book. But what book would you recommend that anybody listening now should stop everything to go read?
Buster Benson: Oh wow, there’s so many books, well actually…
Alison Jones: So many books, I know, right, so little time. I know. But just one.
Buster Benson: I am really thinking a lot about this book I just read this year, it was last year at this point. But, How To Do Nothing by Jenny Odell is one of my favourite books. It’s just so good, it’s surprisingly not about how to do nothing, but what it is about, is about how really to find yourself, how to become the human that’s not just a producer of efficiency, and capitalism. But, find yourself and she has a great writing style that I loved and she’s from the Bay Area, too. A lot of it is, also, the subject in that sense. But, I love that book. I don’t know if you’ve heard of it, but it’s really good.
Alison Jones: I have not heard of it, and it sounds really interesting. I love it when people come up with something like that. I love the sound of, and haven’t read. So, thank you, I will get that onto the reading list. I am trying to read 100 books this year. I’m way behind, all I’m really interested in is the 100 pages. Just give me the short books right now, just the collected blog posts, or something. Yes, I will put that on the list for next year. Thank you, that sounds really great. Buster, if people want to find out more about you, if they are intrigued by your Codex Vitae, and your Piles, and all the stuff about you where should they go?
Buster Benson: BusterBenson.com is my website, it’s got all kinds of weird stuff. Twitter @buster, those are probably the two best places. I am always open to a conversation on Twitter. Most recently I’ve really liked using letter.wiki, which is a place to do long forum correspondence in public, so that’s another place where I have a lot of stuff recently.
Alison Jones: Oh wow, I hadn’t heard of that. I mean Medium is the really sort of long form blogging platform, but this is actually correspondence?
Buster Benson: Yes, it’s two people talking about something, in public in a long-form format. It’s almost like a text-based podcast.
Alison Jones: That’s great. Actually, that feels quite historic, as well. Like the great letters that the great men and women of letters used to write. The Oxford Book of Letters is one of my favourite reference books of all times. Love that. Going to check that out, brilliant. Buster thank you so much for your time today, it has been fascinating.
Buster Benson: Thank you, it was a joy to be here.