The hardest thing in the hard craft of writing is not choosing words and phrases. With practice, a routine, and perhaps a helping pair of eyes, the words usually flow at a reasonable rate. Rather, the hardest thing is the careful construction of an argument or plot. All writing, bar the driest reference material or the most avant-garde literature, must tell a story. For example, a market research report (at least one that’s any good) weaves the data into a coherent plot, with an actionable denouement. A help page starts with a goal or problem and finishes with one or more solutions. And email should be the haiku of business communication. A sentence or two to frame the topic; some more for the details; and then an unambiguous statement of the necessary action. But it’s difficult to wrestle a wriggling mass of ideas into a coherent structure.

To apply ourselves to the task, we need focus. We should have a reasonably quiet space, without music¹ or notifications. At this crucial stage of plot construction, we may want to disconnect our umbilical Web links and rely on our own mental oxygen. And what we really don’t need is writing tools that constantly break our chains of thought. The worst tools at this stage are those which force you to focus on the visual structure of your writing, rather than the inherent or logical structure. It’s still too common to start a piece of writing by opening Word and selecting “Heading 1” (or even the “B” button — urgh).

But perhaps things are changing. There’s a new breed of “distraction-free writing tools”, which feature simple interfaces with very few formatting controls. Some even let you focus on one sentence at a time.

Most of these tools use a plain text markup language: Markdown. This has a lot going for it. Much of the formatting markup is based on email plain-text conventions — especially nice for those of us who still miss Usenet. And it’s predictable — for some applications, it works well as a storage or transfer format. Right now I’m saving this post in my /Dropbox/Blog/content/2013 directory. Later, I’ll use Pelican to rebuild and publish the static site directly from there, with just one command. And if I later move my site to another platform, it will be no big deal to move my posts over. However, while Markdown can be very useful for the later stages of writing, it has limitations when it comes to planning structure. It’s still just too tied to the presentation format.

Let’s say I’m doing rough notes for a requirements document. I’m working on an unordered list of items, when I realize that I need to go into more depth for each one. Instead of running to nested lists, I decide to raise my bullets up to become headings. So I then carefully change my Markdown, adding newlines and changing * to #. Not much, you might think. But it’s enough to make me lose my train of thought. When we’re wrestling our ideas into shape, the last thing we need is to be forced to decide whether they’re bullets or headings.

One of the best ways to plot a piece of writing is to forget digital devices and draft your sections on pieces of paper or index cards. Spread them across as large a space as possible: your desk, a whiteboard, a desk, or even the floor. To rearrange your story, just shuffle the pieces around. And as things are start to coalesce, use sticky tape to link sections and arrange the hierarchy. (I suggest masking tape: you’ll appreciate it when you need to unstick and change things around.) Writing by hand and reorganizing ideas in physical space seems to help the thoughts flow.

But if your workflow has to stay digital, another breed of tool comes in really handy: the outliner. In essence, this provides infinitely nestable lists. Keyboard shortcuts let you indent or dedent list items, or move them around in the list. That’s it. What do the list items represent? Whatever you want them to be. They could simply be a sequence of paragraphs. A parent list could be headings; and sublists, paragraphs under those headings. Or the parent could be menu options, and the sublists the consequences of selecting those options. Or tasks and dependent subtasks; products and their properties — the list is endless (sorry for the pun).

There are many such tools — Tree, OmniOutliner, etc. There are more options on OS X than Windows, but even Word features a surprisingly uncluttered outline mode. Most outliners work with documents, on your filesystem. But what if your document itself becomes part of other documents? Perhaps a tool called Workflowy is more suitable. All your notes are stored in one vast outline. You can zoom in to any node, so that node in effect becomes the current document. But if you need to “merge” or “split” documents, you just zoom out or in. No need to mess around in the filesystem. Another distraction removed.

The convenient UI aside, the most important thing about outlining tools for our purpose — the sketching of an argument or plot — is that an outliner physically prevents you from being distracted by the final visual representation/s of your content. In a pure outlining tool, you cannot specify what fonts you want users to view your thoughts in; what bullet and number styles you want; or even what is a heading level and what is a list. You are forced to think only of the sequence and the bare hierarchy. And that’s just what you need when you’re wrestling a story into shape.

A note on outliners and structured content

From a structured content point of view, the interesting thing is that you actually lose very little semantic information in this way, compared to working in a tool such as Word or (Unstructured) FrameMaker. It’s true that tables can provide a better view of certain relationships, but for the most part, your DTP-oriented styles may just as well be represented by the nesting of lists. Could the ease and simplicity of outliners be extended to a full-blown structured authoring environment? More on this in my next post.

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Music can impair creative thinking:

Many of the everyday tasks performed by professional workers are done in the serial processing center of the left brain. Music will not interfere particularly with this work, since it’s the brain’s holistic right side that digests music. But not all of the work is centered in the left brain. There is that occasional breakthrough that makes you say “Ahah!” and steers you toward an ingenious bypass that may save months or years of work. The creative leap involves right-brain function. If the right brain, is busy listening to 1001 Strings on Muzak, the opportunity for a creative leap is lost.

From a discussion of a study at Cornell University in DeMarco, Tom; Lister, Timothy R. (1999). Peopleware: Productive Projects and Teams, Second Edition. Dorset House Publishing.