November 03, 2022

Stowe Boyd on Obsidian and Taskidian, learning loops, work management, and sedimentary thinking (Ep38)

“People have to dedicate a chunk of time to actively make sense of the world every day. That is get out your diary and write all the thoughts you had in your head and didn’t have time to synthesize until you woke up this morning, or read the things you think are most critical to read and take notes, and capture chunks of information that you think are going to be of relevance to you in the future. You have to make that investment.”

– Stowe Boyd

Tim O'Reilly

About Stowe Boyd

Stowe Boyd has been studying work and the tools we use to adapt to the future for the past three decades. Stowe coined the terms ‘hashtag’, ‘work management’, ‘social tools’, and ‘spreadbase’.

Website: Work Futures

Blog: Stowe Boyd

LinkedIn: Stowe Boyd

Twitter: Stowe Boyd

What you will learn

  • What is the following people model? (03:14)
  • What are the advantages and how to use Obsidian (06:12)
  • How maths is a tool for connecting information (10:08)
  • How can we thrive on overload as individuals and as a team? (16:48)
  • What is the role of visuals in complementing words and its role in organisations (19:00)
  • How to nurture the process of synthesis and pulling together into a whole all of the disparate things that we see (23:19)
  • Why you need a daily routine for information processing (28:14)

Episode resources


Ross Dawson: Stowe, it’s wonderful to have you on the show.

Stowe Boyd: Nice to see you again, actually, it’s been a while.

Ross: It has been a very long time now. I think it’s fair to say, thrive on overload, you make sense of the world of work and where that’s going amongst many, many other things. Where does that start? What’s the starting point for you in being able to make sense of this incredible world of information that we live in?

Stowe: I guess the start, in a way, was the transition from the old world onto the internet. I’d gotten involved with that relatively early and embraced all that that entails, the good and the bad. I started blogging in 1999. It was a long time ago. Around the same time, I got really interested in the transition to collaboration technologies, as most people call them, but I use different terms. I followed that very avidly for the last 20 years, honestly. That was the grounding of everything that came later. From that, I got interested in work; what people are doing aside from just the technologies that they use to do it. That’s basically the background, the foundation of everything else I’m involved in, or have been involved in for the last couple of decades.

Ross: Why don’t we start from the tactical and build out into the macro of what you do? How do you choose your information sources? Where does your sensing of the world stand? What are your sources? What times of the day do you do that? How do you get to come across the things that feed your mind?

Stowe: I’ve always been a real fan of the following-people model. I once said that the most important decision in a connected world is who you choose to follow. That’s a lot of it. There are specific people, hundreds of them out there, that I think highly of and are good sources. I try to follow them in whatever mechanism that comes; Newsletters now is very common but also before that things like Twitter, Tumblr, Medium, and all those kinds of platforms. That’s it principally; that and, of course, certain journals, periodicals that I think are important, MIT’s Technology Review, for example, or the New York Times, real obvious things. I’m pretty avid about keeping up with those sources. I have a deluge of newsletters coming to me all the time these days.

Ross: Following these people, finding these sources, how do you pull out what is relevant? Something which you do need to capture or to do something with, how do you identify what it is? What do you do with that to pull that into your framework of thinking?

Stowe: I think I’ll operate on this Feynman notion that you have a list of 20 questions or 12 questions or some number that are important to you so you’re always on the lookout for information that adds to, clarifies, or debunks things you’ve already been thinking about. I definitely have that. I’ve got this list of topics and when they reoccur, I’m very interested, I capture, read, and try to assimilate it. I was doing this in the morning before we got on the call. I was reading about this characterization of the two sides of the world, virtuals versus physicals, and people are grounded in those worlds.

This aligns with other discussions that are important to me about how does the world work, and how is politics and economics changing. I copied two things that I was reading this morning, put them in my Obsidian vault, and highlighted the things I thought were critical. Sometime in the not-too-distant future, I’ll go back and write something, and pluck that quote from Christopher Lasch and that other thing from N.S. Lyons and it’ll find its way into something that I synthesize and try to help me make sense of the world, then I’ll share it somewhere.

Ross: So you’re using Obsidian. I’d love to hear why you’ve chosen to use Obsidian and how specifically you use that to capture and connect.

Stowe: It’s the most recent example of trying to use and maintain a body of information, what I call “My Workings” and you’ve got to keep it somewhere. In the old days, people would keep a commonplace book and write on the pages or take clippings from magazines and glue them in whatever. But, in the digital age now, I’ve tried a whole bunch of other tools. They all did what they did, and they sufficed maybe at various points in my progression. I have gone through Notion, Evernote, and a bunch of others, too many to name actually.

Then, in the last year and a half, I’ve been using Obsidian, and I really like it because of its flexibility. I mean, the fact that it’s extendable, that people have built all kinds of plugins that do all kinds of interesting things, that makes it easy to cross-reference and find things. Finding is really critical. I need like 100 ways to find things because my memory is flawed and limited but I can have an infinity of markdown files on my hard drive. I want to be able to go there and say, who was the person that said, who was the guy that wrote the book The Revolt of the Elites? I don’t remember. I know today because I just put something in there but six years from now, will I remember that? Maybe, but maybe not. But I’ll search it and I’ll find out. I really require a system and Obsidian is one of many candidates that I am currently invested in. But it’s not necessarily the end-all and be-all, who knows? I might move again.

Ross: I’m using Obsidian as well. There’s Roam Research, Obsidian, and Logsec and some other similar tools. Do you think there is potential for the next generation beyond that?

Stowe: They’re evolving very quickly, they’re all on their own development paths but they’re all looking at each other like, they have that feature, I’ll implement that. Yes, it’s another interesting frontier technology space, very interesting stuff.

Ross: You connect some when you take notes, whether that be a paragraph, an idea, a link, or so on, are there any particular ways in which you’re trying to connect that or link that to build a structure to those notes?

Stowe: Yes, absolutely. I built a system inside of Obsidian I call Taskidian. It’s based on some plugins, Data View, Query Tool-a plugin, and it allows me to put metadata associated with tasks and then I can find them later, I can search, I can order them by the metadata values, and so on. I also use extensively Kanban boards inside of Obsidian. For everything I consider a project, I’m managing the information that way. That’s manual, it relies less on search and Data View kind of metadata, but because I think in projects, it’s very sensible to have an artifact that reflects the way I think about things too not just because someday I might want to be able to find things in an organized fashion. I have six Kanban boards in my side panel, and I can just click on them and say, what is the next thing I’m supposed to do or who am I waiting for to take the next step in that project. That’s kind of critical.

Ross: You have a mathematical background. I think that is one of the ways in which we have overlapped in thinking about social network analysis and some related fields; you mentioned Set Theory, and so on. How do those frameworks inform how you think, how you find information, how you connect it, or how you find that again?

Stowe: There are fundamentally two kinds of math, discrete math and calculus and that kind of approach, and then different tools, different ways of thinking about the world. I studied both, but my real background is computer science. It’s Set Theory and Lambda Calculus, Recursion, and all those kinds of things. Those things fundamentally structured my brain to think about things in different ways than I thought before I learned them, clearly. That means that when I look at something, I tend to use those kinds of tools to try and make sense of it.

Then I learned all about Social Network Theory; the concepts of that and social network analysis obviously frame a lot of my thinking about how people interact in social groups, and so on. That’s 85% of what goes on in thinking about work, the workplace. The other 15% is technology, and how that’s influencing it, and the influence of external factors like the economic sphere in which businesses operate, and so on. Those tools are absolutely central to what I think about. I use those models as ways to structure, framework things, and help explain them to people because a lot of my work is explanatory in its nature, trying to teach things, drawing correlations between things and sharing them with people, and say, hey, you should think about this way, as opposed to some other way.

Ross: The correlations or the relationships between ideas, I asked you the question before we spoke on around surfacing relationships, where are the connections? How do you identify them? You made some interesting points around the analogies or how you are making the connections between things cognitively, which, to a fair degree, is connecting the dots in ways that other people wouldn’t. What are the thinking structures that enable you to make these connections?

Stowe: Here’s a good anecdote. I was working on a panel session recently, all virtual, it was kind of interesting, and I came up with an analogy during the talk while I was actually moderating this panel, which was a similarity between people’s reluctance to retreat from rising sea levels along the coastlines and instead, their natural tendency to rebuild over and over again which is going to be fruitless because the problem is just getting worse all the time. I made the analogy from that to how companies continue to invest in building teams as a central part of how to manage work and how to organize people in businesses even though all the evidence shows that mostly companies don’t get a return on investment from teams, that they’re not a great way necessarily to organize the totality of work. But we will continue to reinvest in teams because people want them to work despite the evidence that it’s not necessarily the best way to organize things.

There is a real similarity there but how would you take evidence from the world of retreating from the coastlines and apply it in the business context? Maybe it’s only the analogy that is applicable, but maybe not, maybe there are actual techniques that could be applied. That’s how reasoning by analogy can actually lend itself to insights, new ideas come from that, who knows? Or maybe it’s just a wisecrack, I don’t know.

Ross: That’s the thing where all analogies have some points that can be mapped against each other and others where they can’t. You always need to distinguish. You can make an analogy that is strong, useful, and relevant but you’ve got to be able to discern where the analogy applies and where it doesn’t apply. Because analogy is not complete mapping so there’s always a danger as well as value when you introduce analogy.

Stowe: In the two cases in this particular instance, now people are talking about “unteams”, actually organizing things that are looser, where you do less team development, that people don’t have a sense that they are going to be working in close contact with this specific group of people over a long period of time. That drops out a whole bunch of politicking that goes on in team formation, the storm-norm model, you can just drop that out. Swift trust is something that’s been well-researched so there is a whole body of things that arise from this. I haven’t gotten around to writing much about it yet, actually, because it just occurred like two weeks ago.

Ross: That brings me to another really interesting point, something which I’m thinking about a lot. I’ve been looking at these ideas of thriving on overload from an individual perspective, as individuals that process information and make sense of it, hopefully to make better decisions. But how do we map that then onto a team perspective, where as a team, we are collaborating to make sense, filter information, create things? In looking at the future of work and your structures, do you have any directions or thoughts around how it is we can collaboratively engage in that filtering, deception, and sense-making and model making?

Stowe: Yes, I think there are a couple of observations. One is that each individual to whatever extent it’s possible needs to invest themselves into a process, doing it individually. As I said, all social tools start with Social Equals Me First. You’ve got to get the thing working right for the individual, and then scale it up from there. I think one of the fundamental insights that I’ve come up with, or I believe now, it’s a belief, is that we need to spend more time writing and reading and less time in meetings and talking. I’m still a believer in talking. It’s just that we have given it too much priority in the business context in group interactions. I like the idea and all the research. It’s fascinating about the value of asynchronous communication mechanisms. They also tend to balance out the differences in people’s cognitive styles whether you’re an introvert, extrovert, Night Owl, morning lark, or whatever, all of those things get smoothed a lot by shifting to asynchronous writing as a mechanism and away from the face-to-face, real-time conversation as a foundational notion of how people should interact socially. The benefits of this then accrue to the degree that people can and do invest in that as a mechanism for coordinating work, communicating, and so on.

I think that’s foundational, but it’s one of those problems because the fundamental thing behind it is the notion that there’s a learning loop going on inside of organizations and it has to be given primacy, it has to be considered as important as what most people think is the central loop of business, which is producing products or services and delivering them to clients. That’s important. You’ve got to do that. But you also have to spend time on this learning loop, or else you’re failing on any kind of sustainable level for people. Likewise, now, of course, we know that there’s a third loop of well-being, we have to figure that out, or else once again, things fall apart.

Ross: One of the interesting things from what you’re saying there or is a part of it: Writing is a process of actually structuring your own thoughts as well as communicating those to others, it is a way of being able to, in a way, distill and build your mental models. But some of the things that you’re saying there, I think, also maybe lend themselves to visual representations. We have words as a way of capturing, distilling, and communicating, but also visual representations is a way. Loops, for example, are difficult to represent using linear words. So I’d love to just hear about as a compliment to words, the role of visuals and how you think or find those useful or how you see those playing their role in organizations?

Stowe: In some of the things I’ve written recently about these very issues like the series I did in the first half of this year for Cisco at their Webex Ahead website if anyone wants to look at it, I use the diagrammatic techniques of loops and show how our loop connects with the loops of our clients or whatever. Yes, I did that. I put the graphic in there so I can save the 1000 words by showing the picture. I think that’s critical. The same is true of all kinds of other models. I’ve shared with you the notion of my adjacency matrix kind of model of thinking about competitive structures, competitive forces inside of markets, like the marketplace for work technologies, there are all these overlapping circles and you can actually show how people move from one end of this matrix to another by changing the functionality of their tools and how people are moving from a sector and a collection of technologies to others because they are offered new and different things.

For example, the transition away from work management, like task-oriented tools to things like what we were talking about, Obsidian, and other tools for thought, what I call Workings, content-centric work management. There’s clearly a movement that people are trying to embed the notion of work management inside of the context of the content, and sharing that among people, and not separating them out as something. That transition is happening based on people deciding it’s a better way, some subset of the people think it’s a better way for them to do things. Will that be a tidal wave that will sweep the world of business? I don’t know. But it’s clear that there’s a lot of investment of human energy in it and also, a lot of investment of capital is going in there.

Notion is now valued at $10 billion, that’s a pretty significant uptick in just a couple of years. I think it’s a fascinating space. It represents a change in how people are thinking about thinking about things, that’s an unusual thing. It doesn’t happen that many times in a generation.

Ross: It hasn’t been done enough. John Borthwick of Betaworks a little while ago had a little Twitter thread where he said to somebody the fact that the thinking tools market is not developed and there needs to be a lot more, it’s fragmented. Yes, we do. We can be helped by tools for thinking. We do have a bit of our next generation but this is potentially a bit of a wave of new software, new structures, new processes, then visual level, organizational level where we can have tools that enable us to think better, make better sense of the world and make better decisions.

Stowe: Right. Let’s hope so. But at least continue to make decisions and maybe make the making of decisions easier, not necessarily just better. It would be great if we could set up systems that would help people collectively organize themselves around decision-making in a better way because the way that decisions are made often is pretty horrible.

Ross: Adjacent to that or in forming that is that space of synthesis. I always believe this is the vital human capability of being able to see all the pieces across different domains and different frames, and pulling those together to make sense to have a synthesis, I’d love to hear any thoughts around how you nurture, support, enable, or go through that process of synthesis and pulling together into a whole all of the disparate things that we see.

Stowe: One of the things I’ve come to appreciate in maybe the last 10 years is that thinking synthetically requires time. It’s something that I didn’t appreciate as much prior to this last decade anyway. It’s like a sedimentary process. You have to lay down layers of things over time and think about them incompletely. There’s an incompleteness that goes on, you haven’t concluded yet, you’re not even sure what the conclusion is, and you don’t know where it’s going. There is this openness to ambiguity. I think that’s essential. You have to accept that you haven’t come down on an answer, or you don’t have the answer, you don’t know exactly where it’s even headed. I think that runs counter to the go, go, quick decision-making which is a sign of leading executives, that kind of grind culture thinking has a tendency to push us away from the necessity for reflection overtime on issues that are if you will, top-level issues, the 12 key questions that someone should be pursuing throughout their life or career, whatever.

I think people just don’t give it enough time a lot of the time. They’re too abrupt, they’re looking for quick answers, quick hits. For example, I’m working on a committee here in my city, appointed by the mayor. He charted us at the very beginning with finding the quick hits, what are the things we can do with the biggest impact for the lowest cost in the shortest period of time? I’m like, okay, we can also do that but don’t we have to do the other thing, too? I mean, how would you know a thing is short-term than something that’s long-term if you don’t consider the long-term things too? Because how would you even make that comparison? We did that. We did that for the mayor even though we ultimately had to spend an equal amount of time or even more time on the long-term issues. It’s essential. His hope for a two-month turnaround of low-hanging fruit, as he called it, meant that we ultimately went on a course that is now two years long, and we have the matrix of the low-hanging fruit, short-term, low-cost, easy, all the way to long-term, expensive, biggest impact. You have to do everything. I think that’s a common situation and it’s inescapable in a way.

Ross: I love that idea of the sedimentary layers, being able to lay those foundations, appreciating timeframe, understanding what timeframe you’re thinking, and for a start, is something which is often neglected.

Stowe: I think of a model, once again, something we’ve been talking about a lot. I think about the Pace Layers of Stewart Brand, the world has different layers, and the ones at the core at the bottom in his diagram are the slowest, but the fastest ones is like, in his example, fashion is constantly changing at a very high pace, but that impacts a lower level, and there’s some friction so that the things that go on in the fashion level influence the next layer, and that causes it to move and so on. But I think thinking about things that way is essential. That’s the kind of thinking that you don’t hear in corporate boardrooms. They think of everything as like quarter to quarter, we’ve got this project, it’s going to go an entire 18 months, it’s like, don’t you have a five-year time horizon or a decade? We’re going to be in a decade in a decade from now, you know it’s inevitable! You have to think about it. No, but often it’s the opposite. I think that’s a difficult thing. It’s a difficulty in the way that we think about time.

Ross: It is. So, just in rounding out, of course, there’s real richness and depth to what we’ve just been able to touch the surface of in our conversation, but are there any recommendations that you would give to people listening to your experience to be able to say, how is it that I can make some steps to be better at making sense of this world of information profusion that we have to deal with?

Stowe: I think people have to dedicate a chunk of time to actively attempting to make sense of the world every day. That is get out your diary and write all the thoughts you had in your head and didn’t have time to synthesize until you woke up this morning, or read the things you think are most critical to read and take notes, and capture chunks of information that you think are going to be of relevance to you in the future maybe. You have to make that investment. You have to be an active participant in the sedimentary nature of building up knowledge of the world. Otherwise, it won’t happen or it’ll happen obliquely only, indirectly, things will happen but you won’t have something that you can turn back to and use as a tool if you don’t craft it.

In my case, for example, I have the luxury, if you will, to say I’m not going to take any phone calls in the morning unless it’s an emergency. I get up at six o’clock, I’m at my desk, and I try to make sure I don’t have any phone calls till 11 or after lunch, whatever. It gets broken up because of travel, client engagements, whatever but I start with the premise that there are no time slots that you can book when I send you a link to my request for the meeting. There are no time slots in the mornings because I want to spend that time reading and writing. At the end of 20-plus years, it starts to add up.

Ross: Absolutely. That’s really important advice that just simply take the time, take the time to think, take the time to digest, take the time to make sense of it. To benefit from the fruits of all of your thinking and distilling and writing, where should people go?

Stowe: There are a couple of places. One is where I write mostly about work-related issues. I have an interesting story about that. It’s too long to tell but basically, I got a big boost from spending time talking to my readers to help me craft a description of what it’s all about, which is really helpful. If anyone wants to see it, was really informed by a discussion with readers of the pub. The other things, I’m on Medium, I work the streams on Twitter every day, and still works, although that’s mostly like culture things these days.

Ross: Fantastic. Thank you so much for your time and your insights, Stowe. That’s been really valuable.

Stowe: Thanks for having me.

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