A Writing & Thinking Experiment

I’m experimenting. I want to explore a different way of writing, so I’m using a simple Markdown writer, iA Writer, to write this.

Thomas Edison, in his laboratory, experimenting. Wikimedia Commons.

It may go nowhere, but my hypothesis is this. Using a writing tool that is more fundamental, more stripped down, I will find it easier to start and finish each thing I want to write. If I’m right about this, starting and finishing more of my written work would be the result I’m looking for.


I’ve used all kinds of things to capture thoughts and notes over the years — text editors, Mars Edit, Wordperfect, Wordpress, Microsoft Word, Google Docs, Evernote, Apple Notes, Pages, Scrivener and more. Each tool has been more or less helpful — some far more helpful/useful/powerful than others — depending on task, context and content. I first began using Microsoft Word in 1984 or 1985. In the late 80s and early 90s, the Mac hadn’t managed to get much traction in law firms or large businesses. So after law school, when I joined my first law firm, I switched to Wordperfect, which turned out to be a pretty terrific program for accomplishing what most lawyers needed a word processor to do.

By 1990 or 1991 it had become obvious to anyone with an interest in tech that Microsoft would soon win the battle to make its operating system and its application software the industry standard. I spearheaded the move, at two different law firms, to switch to Microsoft Word. But I long ago fell out of love with Word. It became laden with features and bloat. With each new bell, whistle and capability, each new set of menus to help users navigate through an almost incomprehensible set of frames of action, reference and perspectives, it became a less and less satisfying tool for the simple (and complex) act of writing.

For a long time, Google docs has been my go-to for creating new, written content — whether long form or short form. It’s incredibly simple. But its most compelling feature has been its ability to provide an easy access group editing mode. I write something. I send it out for comments and suggestions. I get back suggestions as a series of markups to accept or reject. This functionality bundled into Google’s suite of products made it the ideal “go-to” for people like me who work in and with startups.

Still Haven’t Found What I’m Looking For

So why am I still searching? What prompts this experiment? A few things, really. First, I want to create content using an interface that is really really simple, but that gives me ready access to keyboard commands for pretty much everything I want to do. No clutter. No menus. No distractions. Second, I want to be able to create that content on any device I own. I’m locked into the Apple system — Mac, iPad, iPhone — the tool I use to write has to work without fail on all of these devices. Third, I want to be able to catalog, reorganize, tag and connect/reconnect things I’m writing. The thing I’m writing in this moment may well find is place as a part of some larger thing that I’ve not yet written. So where does this thing, this smaller piece, live? How can I search and browse efficiently? How can I rearrange what I’ve written to bundle or unbundle elements at will and in real time?

But here’s the real kicker. I want my writing to be connected to and empowered by my computer. And I mean this in a way that’s much different than what is possible using any of the writing tools I’ve referenced. I really want to use computational power to surface and explore relevant links between things I’m writing and things I’m reading (or things I should be reading). I want the computer, the database, the analytics, the AI to connect certain dots for me — based on whatever connections I might tell it I’m looking for or based on its own ability to identify patterns in the material.

Here are just a few practical examples. I’m reading and writing a lot these days about complex systems and wicked problems. As part of that work, I’ve spent significant time reading and learning about systems, design and different approaches to problems. There’s a clearly a link between “wicked problems” an expression that came into its own via the 1973 Policy Science article, Dilemmas in a General Theory of Planning, by Horst Rittel and Melvin Webber and “design thinking,” a framework identified with a sizable group, including John Arnold, Bruce Archer, Herbert Simon, David M. Kelley (IDEO), and Richard Buchanan. But this link isn’t immediately obvious. Wikipedia’s piece on design thinking calls attention to it, but I originally had to discover this link on my own.

To take this example a further step, I haven’t found many written works that link the notion of complex systems (e.g., Jay Forrester, Russell Ackoff, Donella “Dana” Meadows, etc.) with wicked problems (Rittell & Webber). But these three things — complex systems, wicked problems and design thinking — should surely be explored together.

Here’s another example. In Elinor Ostrom’s book, Governing the Commons: The Evolution of Collective Action, she mentions from Garrett Hardin’s frequently cited article, Tragedy of the Commons. I’d not read it recently. When I reviewed it, I was surprised to discover a few things. Hardin begins his 1968 article by calling attention to the class of problems for which no technical solution can be found. (He also references Tic-Tack-Toe at length in a way that leads me to wonder whether the writer of the “War Games” script was a Garrett Hardin fan.) But Hardin also explicitly calls attention to a dawning awareness in his time that the natural sciences and technology were not going to solve all of humanity’s problems. And he does this with language that maps in clear ways to Rittel and Webber’s later work, Dilemmas in a General Theory of Planning. Both Hardin and Rittel & Webber were determined to call attention to the distinction between the kinds of problems that can be solved by science and technology and the kinds of problems that cannot.

Back to what I’m looking for. I’m looking for software, data, analysis and computational capability that can address a particular problem. Fortunately this problem is not a wicked problem. No, it is precisely the kind of problem that technology can solve. I want computers to do what they were built to do.

I already have tools to write. I have tools that let me grab content from almost anywhere on the web. Scrivener, for example has both of these things, and it has some wonderful tools for organizing research and editing/reorganizing my drafts. But what Scrivener does not have, what none of the software applications or tools I mentioned above provides, is a way to take (1) the raw material that comes from my writing and preferences and (2) my personally directed curation of web-sourced content and turn this mess into possible links, connections, insights and trailheads. One of the earliest conceptual articulations of this was Vannevar Bush’s “Memex,” described in As We May Think (The Atlantic Monthly, 1945).

Consider a future device for individual use, which is a sort of mechanized private file and library. It needs a name, and to coin one at random, ``memex’’ will do. A memex is a device in which an individual stores all his books, records, and communications, and which is mechanized so that it may be consulted with exceeding speed and flexibility. It is an enlarged intimate supplement to his memory.

Bush went further.

It affords an immediate step, however, to associative indexing, the basic idea of which is a provision whereby any item may be caused at will to select immediately and automatically another. This is the essential feature of the memex. The process of tying two items together is the important thing.

When the user is building a trail, he names it, inserts the name in his code book, and taps it out on his keyboard. Before him are the two items to be joined, projected onto adjacent viewing positions.

Much of what Vannevar Bush had in mind, of course, has already been realized and surpassed. The computers and other devices we use today, the software these devices can run, the networks to which we connect, the algorithms that drive these applications and connections at speed — all of these things are amazing.

But while I suspect all of this would have delighted Bush, I don’t think he’d be satisfied. On the contrary, I suspect he’d say, “That’s all you’ve got so far?” I think he’d have wanted just what I’ve been trying to describe. A way to get our computers to help us think more clearly. I don’t think that’s too much to ask. Do you?



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Tom Higley

Tom Higley

Wicked Problems. Founder Opportunity Fit. Entrepreneur “success” at the intersection of ROI & impact. Co-founder & CEO, X Genesis. Founder 10.10.10. @tomhigley