2022-10-04 Stowe Boyd's answers to Dawson's questions

My answers are in italic.


  • How has clarity on your purpose or objectives helped you in thriving on information overload?

I have submitted to my obsessions, and I am not striving for clarity of purpose so much as depth of purpose.

  • Is there a story on how you clarified your information intentions, across your life, work, or other domains?

I recently participated in a Substack Grow workshop, over six weeks this past summer. One of the exercises entailed characterizing the readers of Work Futures, and then recrafting various explanatory materials to match their orientation. I recruited the readers as participants. It led to some great results, and this new tagline: The economics and ecology of work, in a time of accelerating uncertainty in our lives, society, and business.

  • How have you selected and focused on your areas of expertise (and how have they evolved)?

I started as a computer scientist, focused on language theory, compilers, and programming environments. Programming environments (IDEs, like Github), led me to thinking about collaboration in general, so I became an analyst tracking what I call work technologies, like work management tools. That led me to my primary focus these days, which is the ways of work, encompassing technology but transcending tech into human affiliation, organizational systems, and the psychology, sociology, and anthropology of the workplace.

  • How have you balanced developing deep expertise with the breadth to connect and apply it?

I hope I have. Mostly by reading omnivorously and writing about what seems important.

  • How do you balance all your information interests including your work, society and politics, wellbeing, and personal interests?

I am not trying to balance: I am simply riding the wave of my obsessions colliding with each other.

Framing/ Frameworks

  • Do you develop visual or other frameworks that help you make sense of new information?

Yes, frequently.

  • How do you use visual or connected note-taking tools such as mind maps, concept maps, Obsidian/ Roam etc or other approaches?

Yes. As I detail later on, I use Obsidian as my commonplace book, based on a daily note paradigm. Obsidian's mindmapping and diagramming tools are not fully-fleshed out, yet, so I use other tools as needed.

  • Have you sometimes used existing frameworks to help you identify signals or useful information?

Yes, certainly. My background in applied mathematics (computer science) included a focus on set theory, networks, and lambda calculus for example, so social network analysis (like Granovetter's Weak Ties) followed, as did building models applying system dynamics and recursion. Indeed, I believe a grounding in these maths is necessary to understand how things work (or don't work).

  • How do you surface relationships between ideas in your area of expertise?

At the superficial level, my commonplace book is riddled with tags, shared references to specific ideas, people, and organizations, and cross links. I can find all instances of a specific idea in economics in a moment or two, for example. At a more conceptual level, synthesis of commonalities and 'distant analogies' comes through writing, supported by the spiderweb of connections in my workings.

  • Have you found scenarios or other foresight methodologies help you filter information?

Yes, I have used probable futures in various forms, informed by Stuart Candy and Jane McGonigal. An example is this piece at Wired: What Will a Corporation Look Like in 2050? .


  • How do you select your information sources?

The friends of friends model. Things find their way to me based on who I follow. I once wrote 'In a connected world, the most important decision is who to follow.'

  • Do you have any conscious relevance checks for new information?

I research the source.

  • Do you use any tools or methodologies to check facts, assess sources, or find original source?

The provenance of the source, mostly.

  • What formats (text, video, audio, digital/analog) do you prefer for particular types of information and why?

Text with visuals. I am not a video person.

  • Do you use aggregators for news and updates? Which ones, and how do you use them in your information mix?

Mostly my aggregators are writers, not tools. So Dense Discovery by Kai Brach is way better than Google News, for example.

  • Are there any specific digital information filtering tools or platforms that you use?

Obsidian. And if Medium or Twitter are platforms, then them, too.

  • Do you use any ‘hacks’ for making social media feeds more useful to you?

I have a hack set up so any tweet I 'heart' gets passed along to a folder in Obsidian.


  • How do you manage and enhance your attention?

I block out mornings for cognitive work (reading, writing, researching, etc.), and accept meetings in the afternoons, preferentially.

  • How and when do you scan your primary information sources?

As early in the AM as possible, reading various regular sources, principally via newsletters (in email), twitter, medium, and other streams.

  • Do you use any particular note-taking techniques?

Yes. I use Obsidian as my commonplace book, and have evolved a rich system for managing work and annotations there that I call Taskidian. (For the wonks: relies on various Obsidian basics -- like tags and tasks -- amplified by plug-ins like Dataview and query control.) Taskidian is principally devised to let me annotate research materials (including my own writings), and to connect and retrieve materials as needed. It is a constant practice, each and every day.

  • Do you practice speed-reading, and if so how did you learn?

Not per se, but I read very quickly, and have since a young age.

In college, I was reprimanded by professors for reading a text book on subject X while taking notes in lectures on subject Z. They just talked too slowly for me.

  • How and when do you set aside time for deep focus, and how do you maintain that focus?

Mornings, particularly 5am to 11am. I alternate reading with writing and annotation. Maintaining focus is mostly just keeping calls off my morning calendar, as much as possible.

  • How do you maximize serendipitous discovery of information in your searching and surfing?

I am always on the prowl for new information regarding a few dozen areas of great interest to me. I rely on those I follow in various contexts: certain writers via their columns, newsletters, etc., for example; those that I follow on Twitter; certain topics on Medium; and certain publications, like HBR, Noema, MIT Technology Review, and so on.

  • When and how regularly do you make time to switch off from information and regenerate?

I walk a few miles every day. Most evenings I turn off, watch a movie, read, or attend local organizational meetings. I am on several boards and committees in Beacon NY, where I live.

  • What are your daily (weekly) information routines?

Daily: read the NY York Times selectively; browse Twitter stream, with a great deal of commenting; browse newsletters and updates, generally via email, but also through apps like Substack (where I publish Work Futures); and follow leads that emerge.

I don't have a weekly routine, per se. I live from day to day, and following the cadence of various on-going projects, like my newsletter and various consulting and writing commitments.


  • How do you develop the mental models that support your work and expertise?

I steal liberally, although I have developed several of my models independently. Their development is usually the outgrowth of some insight based on context. For example, I use what I call an adjacency model that array different sorts of work tools along two dimensions: complexity and scale versus flexibility and scope, and communication-centric versus context-centric.

!2022-10-05 work management adjacency chart.png

  • What approaches do you use to consistently improve your mental models?

Not sure that I am consistent in that department.

  • Do you deliberately practice systems thinking or similar approaches to gain insight?

Yes. Especially social systems thinking.

  • How do you question your own assumptions and natural tendency to confirmation bias?

I confess that I reason by analogy, or even by metaphor, a great deal. I don't think of my approach to synthesis and analysis as a project to be improved, but more of an artistic process I have adopted and pursue. Pursuit, not improvement.

  • Do you actively try to be open-minded? How do you do that?

Not as a first-order principle. I follow the practice of 'strong opinions, loosely held'. Although I believe in having a growth mindset a la Carol Dweck, and I am obsessed with on-going learning.

  • What helps you to synthesize your ideas and thinking into higher levels of insight?

Writing, and interaction with others through exchange of ideas. I find humor is critical to breaking through barriers to insight.

Today, for example, in a conference panel on engagement I used the analogy of intentionally retreating from the coastline given climate change as an analog of intentionally adopting 'unteams' (or 'co-acting groups' as described by Constance Noonan Hadley and Mark Mortensen), which loosen the ties between individuals, and adopting more of a hollywood model, without a great deal of team-building. The analogy works because the high level of investment companies make in building teams is often not worth it. But, just as we will see in Florida post-Ian, the natural inclination is to rebuild instead of retreating, even when the houses will just be knocked down again. In business, we keep focusing on (re)building teams, even though employee engagement remains chronically low, and companies don't get the ROI they expect from teams.

This was based on what started as a wise-crack.

  • Does dialogue, teaching or other personal engagement help you to synthesize ideas?

I find 'teaching' -- presentations and talks -- helps me a great deal. See the 'unteams' example, above.

  • How do your information and synthesis practices support better decision-making for you personally?

I've learned enough about human cognition to not trust the fast mind except for things like what to eat for dinner. For bigger, burn-the-boats decisions I go slow, defer the point at which a decision must be made, and remain in fact-finding mode as long (and longer) as possible. I look for others to challenge my premises.

I'm not sure I'm a great decision maker, but it's hard to know when you think abductively, since abductive reasoning reveals a plausible conclusion given a set of observations, but does not 'prove' it.

  • Do you have any decision heuristics or approaches that optimize your information search and filtering?

Von Foester's Ethical Imperative is 'always act to increase the total number of choices', so I start there, but then use various forms of pattern recognition, or sensemaking (a great deal of which happens below the conscious level) to winnow options.

I rely on the fundamental insight that 'the most important decision in a connected world is who to follow'. Also, on a day to day, nuts and bolts level, I am relying on my commonplace book (in Obsidian) to extend my organic (physical) search and filtering: my finite and flawed memory.