November 23, 2022

Greg Satell on writing daily, building your own ideas, seeking different perspectives, and conceptual models (Ep40)

“There’s the experience, what it is we take in the information, and then there’s the output, which can come in many forms just in talking, thinking or writing, and so on. The writing is crystallizing the ideas, which can be a process and come out difficult, but it is this process. What you write then informs what you read or what you input or the things which can shape that to be able to then write something which is even more incisive or better.”

– Greg Satell

Tim O'Reilly

About Greg Satell

Greg Satell is a transformation and change expert, international keynote speaker, and bestselling author, most recently of Cascades: How to Create a Movement that Drives Transformational Change. He is also a lecturer at The Wharton School; his work has appeared in Harvard Business Review, Barron’s, Forbes, Inc., Fast Company.

What you will learn

  • What is the importance of an information routine to get to the good stuff (02:27)
  • Why thinking your own thoughts and ideas is important (04:25)
  • How to leverage your personal information networks to learn more (06:38)
  • How curiosity allows you to uncover what’s worth reading? (10:00)
  • What is the process to build a framework? (16:07)
  • What are co-optable resources and why TedX is the best example of it (18:57)
  • Why we should ask what-if questions (22:57)
  • Why doubting everything you think is the way to thrive on overload (26:32)

Episode resources


Ross Dawson: Greg, it’s awesome to have you on the show.

Greg Satell: Thank you so much for having me, Ross.

Ross: You keep across the edge of change, undoubtedly, in all sorts of interesting ways. How on earth do you do that?

Greg: I just pursue interests that change over time. What I really think is most important is that you put in the work every day. You make sure that you’re taking some time out to read every day. For me, it’s really important to write every day, whether I write something worth writing or not. You put in the effort every day. Often I find myself copy-pasting or writing something that’s not very good, but you really need the reps, you really need to put in the time to get to the good stuff. Somebody once described it to me, you need to let the muse know you’re serious. There’s so much to just putting in the work every day.

Ross: That’s great. What do you write?

Greg: It’s funny. One of my favorite quotes is from Fareed Zakaria, a famous journalist and author in the United States. He says when he sits down to write that the thoughts he thought he had were just this garbled and mumbled chain of a bunch of stuff, he said it much more eloquently than I could, but a bunch of stuff that doesn’t make much sense. Obviously, everybody can’t write. I have other friends who like to do podcasts or do it in other ways. The idea of that discipline of arranging your thoughts to see if they make sense. He’s right. When I sit down to write that great idea I had, I realize that a lot of times, it doesn’t make sense, but that process of working through it – I’ve been doing this for a long time now. I have old thoughts. Sometimes I’ll have a thought, and I’ll say I thought something similar five years ago, or 10 years ago, and I’ll go back to it, and I’ll say that’s interesting, but something else I was thinking, I can build on that now. That’s really how you start building your own idea about things. It’s really important that you are thinking your own thoughts because if you don’t think your own thoughts, somebody else will think them for you. The best indication of what we do and what we think is what people around us do and what people around us think.
We have decades of research that show this is absolutely true. It’s not just the people we know, either, it’s three degrees out, so our friends, and our friends and friends and their friends, many of whom we never met, are all influencing how we think. It’s one of the reasons why it’s so difficult to persuade people. Ross Dawson could come to me and tell me how to think about the future and I think, jeez, that’s a really great idea, he really persuaded me about that. But then what happens the next day? I go right back to those same social networks that form the way I thought in the first place. Chances are, that Ross Dawson’s idea is just going to fall by the wayside because everything else in my environment is pushing me in a different direction. That’s how we get into trouble.
Generally speaking, we take the most available information, not the best sources, but what’s easiest for us to access. It’s called the availability heuristic. Somebody can tell us about traffic accident statistics, and it won’t change our behavior but the second we see an accident on the side of the road, we’ll immediately slow down. If we happen to make a particular observation or just our local information in a certain way, that will form our opinions, and then we’re likely to go out and try and look for data that confirms those opinions and tend to reject data that contradicts our existing paradigms.

Ross: There’s the experience, what it is we take in the information, and then there’s the output, which can come in many forms just in talking, thinking or writing, and so on. The writing is crystallizing the ideas, which can be a process and come out difficult, but it is this process. What you write then informs what you read or what you input or the things which can shape that to be able to then write something which is even more incisive or better. Digging into your point about social networks and this idea, of course, we take information through our screens, or reading or books, whatever, but a lot of it is the people that we connect, we have conversations with, we’re exposed to, are there ways that you leverage your social networks? Sometimes I call them personal information networks, this idea that networks are the people from which we can draw on for our information or insights. Are there any ways in which you try to leverage your social networks to think better and learn more?

Greg: Yes, that was the point I was getting to. You have to be very careful about that because they’re shaping your thoughts in ways that you’re generally not aware of. That’s one of the powerful things about writing is that you’re doing it yourself. If it doesn’t make sense, you’re much more likely to catch yourself. So I think that whole idea of falsifiability and testing yourself and being very careful about things that you want to believe. Because if you want to believe, you’re not going to look that hard for other information. Ideas you don’t like, you’ll check. Again, we know this from decades of studies when people are in situations where they don’t expect to be checked, they don’t expect people to call them on stuff. They’re much less careful about the information they share.
I think everything is it has to be about being careful. You’re right, when you’re inundated with information, it’s important to remember, you’re only getting a sample, a small sample of it, because of your social networks, your location, your time, your geographic location, all these different things. You’re getting access to different information in Australia than I’m getting in Philadelphia, you probably don’t even know who the Philadelphia Eagles are, they’re the greatest football team in the national football and we have an Australian on the team, by the way. It’s important to remember that what we’re seeing is only a small part of the information that is out there so not only do we need to filter the information so that we can understand it but then we have to ask the hard questions, what are we not seeing? How can we be wrong? What’s another perspective? Very much to your point, it’s really important through both social media and also through your social networks to surround yourself with people who challenge you and don’t think exactly the same way you do.

Ross: Going back to the start, you were saying you do lots of reading based on your evolving curiosity. How do you find what it is you read? What formats do you read in? Do you tend to read books or articles? How do your evolving curiosities allow you to uncover what’s worth reading?

Greg: It’s funny, I can’t stand documentaries. I’m not a documentary person. I also can’t stand anything with subtitles. Because I’ve spent so long, I spent 15 years in non-English speaking environments so whenever anybody says, oh, do you want to watch a foreign film, I say, watch them, I’m living in one. Anything I watched became just a pure form of entertainment. I’ve always been very, very partial to books. To grasp a subject, to get a hold of it, you need to read three or four books about it, you can’t just read one book and say, now I understand that. It’s that type of thing when you get interested in something, whether it’s an idea or anything, if it’s worth reading one book, it’s worth reading five books. You have to get to that point where you’ve read three to five books, and you’ve read a bunch of different perspectives on it, then you can start to put it in perspective.

Ross: Do you read a chunk a day? Do you say, here’s a particular time of day that I’m going to read a book?

Greg: I try and read 20 pages a day, hopefully, more than that, but 20 pages a day, or an hour a day, is a good number. I don’t always achieve that. Sometimes I’ll get more, of course. In the beginning of the book, you’re always reading slower. Then, of course, you have to make that decision once you get to about 50 pages, whether it’s still not interesting, whether you’re going to continue to slog through it, or maybe jump to something else that’s a little bit easier to hold your attention. Because your time is important. I always feel guilty when I don’t finish a book.

Ross: It’s a really important precept, if it’s too hard going, just move on to whatever it is that’s enjoyable, which is going to be worthwhile. There are a few. There is very occasionally, a book, which is worth slogging through. It’s not just time, it’s enjoyment. If it’s hard work, then there’s plenty of reading out there, which is not hard work, and which is beautiful and wonderful. We don’t speak enough about just dropping a book if it doesn’t keep enough interest.

Greg: Yes, it is always. It’s funny, you get to that point, and you’re thinking, what’s the value of actually finishing this? And also what’s the value of jumping to another book I can read twice as fast?

Ross: Yes, I think it’s dynamic. Your evolving curiosities, do you track it as in say, okay, this is what I’m interested in now, this is what I’m digging into, or is it just whatever takes your attention?

Greg: I track it through my blog. That’s the way I track it. That’s nice because my blog could just have its 13th birthday in August. I lose track of how many years it’s been, but it’s great to have a 13-year-long record of your thoughts.

Ross: Yes. I’ve been doing it longer, but you’re more consistent than me. I need to get back to being more consistent. It’s one of the things where, for example, you write a book, okay, I can focus on that but when you’ve done that, it’s important to have the discipline to say alright, this is a thing I want to capture, and then write it. I admire your consistency in getting your ideas, really good and incisive ideas out there.

Greg: I have slowed down. For the first few months, it was three times a week. I kept up to two times a week for at least 10 years. Recently, I switched to one time a week, a few years ago, and that’s enough I think, for now.

Ross: You have a nickname or moniker Digital Tonto. I’d love to hear about that because that’s relevant to what we’re talking about.

Greg: When I started my blog back In 2009, it was 2009 in Kyiv in Ukraine and the whole world was coming to an end. I was just online and I was reading this article about why you should do a business blog, and I thought Gee; my wife was nine months pregnant at the time, I went in and I said, hey, honey, I think I should do a business blog, and she was, okay, whatever, she was nine months pregnant. I went back and said, I need a name for the blog, because back then when you had a blog, you didn’t just name it, now I have, but back then, everybody needed a name. It was 2009. I knew it needed to be digital something. Then there was this old joke about the Lone Ranger and Tonto so I thought it was a cool name, Digital Tonto. If I had to do it over again, I probably wouldn’t have named it a Digital Tonto but I think it’s worked out pretty well.

Ross: It has certainly; certainly very well known. For me, it evokes this idea of learning in the digital space. I’m not necessarily the Master or the Lone Ranger, but being at a place where I know I can look out there, and to learn and to find things and discover.

Greg: I’m glad to hear you say that.

Ross: Part of the idea is building your frameworks and your thinking. You’re very widely read, you share all sorts of interesting references and sources in what you do, they’re not just from business books, and so on. But this idea of building your framework of understanding how an organization works, how the world works, how the economy works, and so this is an ongoing process, you capture a lot of these frameworks or these ideas in your blog posts, what’s the process for you to have all of the information come in to be able to build that framework of understanding? Do you use any ways of writing notes or drawing things? Is it all in your mind? How do you develop those ideas and frameworks?

Greg: I really just write, for the most part. I’m not a visual person, I’m not a drawing person, maybe I’m not clever enough because there are a lot of people who are really good at that. They’ll draw things out and their whiteboard things, and I’m not really that great at that. I plod along, and I keep knocking at it until I get something that starts to make some sense. I usually don’t realize it until later. When you’ve put it down on paper and you come back to it six months later, a year later, two years later, if it still makes sense, you’ve probably done pretty well.

Ross: Yes. There is a structure in writing. I’ve been through the process of taking a written article and then distilling it into a visual because there is logic, there is structure. One way of representing is visually and another is through writing, but it’s just as valid. Now, that’s common, the most accepted form in how most people are used to taking an idea. Writing in a structured format does tell the story, it is a framework.

Greg: Michael Port, who does speaker training, has an interesting one that he puts his students through, he calls it content cataloging. The idea is you have an idea, then you have a story and a conceptual model. The idea could be something about this, about the future, what you do, or for instance, in terms of what I do, when we’re talking about scaling change, we often talk in terms of co-optable resources. The simplest one is TEDx.
One of the big challenges about change is that people need to embrace it for their own reasons, which might be different than your own. The challenge becomes what can you give them that they can co-opt as their own to drive this change forward so that you’re not pushing them to change, they are pulling. You’re giving something that empowers them, that promotes change, probably the most successful ever is TEDx. They have thousands of people running around doing all these millions, if not billions, of dollars worth of man-hours or person-hours to promote the TED conference. If you ask anybody why they do a TEDx, they’ll say they do it for themselves. That’s the conceptual model. We have a whole conceptual model around that. You have the idea of how do you scale change. Then there are several different stories that we use to conceptualize that framework so that people can understand it, TEDx is one of them. Those three things where you have an idea, a conceptual model, and a story, that is one of the frameworks I’ve seen, that I found really helpful.

Ross: Yes, that really a good frame there. In terms of just your daily information habits, how do you find, filter, and discover the things which are worth spending your time on?

Greg: There are several newsletters I’ve got about the news. There are things I follow on Twitter. While I’m getting ready in the morning, having my coffee, and waking up, I’m looking at those. Then I start writing. Usually, when I’m writing, I’m writing according to an outline which I’ve written at some random time before [00:22:49 check] penning it. At any given time, hopefully, I have three or four outlines. Once I start running out of outlines, that’s when I get nervous. While I’m writing, I’m usually finding gaps, and I need to go look for other things. When I find those other things, I link them to the outline that I’m using. I will research them later in the afternoon along with whatever book or books, I’m usually reading two or three books in the afternoon or evening, and I try and at least get 20 pages in.

Ross: Does the framework, the article, or the post which you’re writing direct you to some research, things you need to find out, or some facts or some insights or some background?

Greg: Usually, yes. Sometimes I’ll run across something, I’ll run across the article, and then that will form the basis for an outline; or if it’s an academic paper, then I’ll realize that there are pieces missing that I need to go run down.

Ross: There are a couple of levels, part of it’s factual, I was just doing this little post, and I realized to make my case I need to find out the cash on hand of Facebook, which takes a little bit longer than I expected to find. But anyway, so now I know the cash on hand of Facebook, which happens to be 40 billion, which is interesting. It’s part of that framework of having all the pieces fit together and there’s a fact but a part of it is also the context, sometimes we need to dig a little deeper in terms of understanding the particular way a technology is deployed or an example of something so you can start to uncover some deeper and richer things as well as that. The fact of writing means you want to get things right, which means you do the research, and you start to build out your knowledge base.

Greg: And asking what-if questions.

Ross: How would you do that? Give me an example of how that might happen.

Greg: I have a great one, and you’re talking about Facebook dislodged it. Back in 2010 or something. Goldman Sachs gave Facebook a $50 billion valuation. That seemed ridiculous to me. I started building the whole DCF model, discounted cash flow, and then looking around for different estimates of growth because it was private then, and what their profits are, and everything, and it forced me to ask the question, what if Facebook is worth a lot more than 50 billion? When you see this, when you uncover a new fact, is that true? If it is true, what if there’s something else I didn’t realize or wasn’t paying attention to? And always be careful about things you want to be true because that’s where you really go wrong.

Ross: Yes, obviously, from that being able to recognize what it is you want things to be right or wrong, once you start to build that self-awareness, it will put you on track. But that point around saying, I think it’s really interesting when you see something, oh, I doubt that. In a way, that’s the best foundation of research. Doubt everything you read, and then say, how am I going to prove this is wrong or check that’s right, that’s when you start to really learn stuff.

Greg: Right. I wrote something not too long ago because I became fascinated by the idea of Elizabeth Holmes and the Inventing Anna Sorokin, who was this young woman who just convinced everybody that she was rich, and she was running around like a rich person, she didn’t have any money and Elizabeth Holmes, the same thing. They fooled some of the richest, most powerful people in the world. In the case of Elizabeth Holmes, anybody who questioned her, they got their lives ruined. These rich, powerful men were so sure, and she wasn’t producing anything.
That’s the type of subject I really love because that doesn’t fit. That doesn’t make any sense. These rich, powerful people who are extremely accomplished, Henry Kissinger was on that board who you would think would be the hardest person to fool, how could they go hook, line, and sinker on something that has no fact pattern behind it? It was just all smoke and mirrors. I asked myself, what if people who were smart and accomplished are the easiest to fool because they expect to see things others don’t? You go down to the local bar in Philly, those people are much harder to fool because they don’t expect to be smarter than everybody else. I thought that was fascinating to me because once I had that idea, it made a lot of sense. In fact, it’s the only thing that can explain things like FTX.

Ross: Yes. That’s a solitary lesson for all of us to realize that things don’t always like they seem. That’s the joy of digging, don’t take things at their face value, and when you dig then you learn whatever happens.

Greg: Also be careful of things that you want to be true, that Elizabeth Holmes was the next Steve Jobs. Because anybody who asked any questions about it, it became immediately obvious to them that it was a fraud. Many people over the years were whistleblowers. They were just shut down.

Ross: To round out Greg, what advice do you have for somebody that’s looking to thrive in a world of unlimited information?

Greg: Don’t believe everything you think.

Ross: Great advice. Thank you so much for your time, Greg. It’s been a fantastic conversation.

Greg: Thanks for having me, Ross.

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