In search of the perfect writing tool

Good software won’t make you a better writer. But bad software can make you a worse one.

I’ve gone through a lot of different writing tools over the years.

• The Write Stuff on a Commodore 64 in high school
• A combination of MacWrite II (for papers) and pen and blue book (for essay exams) through college and early graduate school
• Microsoft Word through the later half of graduate school through my career in academia
• Google Docs as a journalist

Since moving fully into content strategy around 2010, I’ve blown through a pile of options, including basic markdown editors, Editorially (sad face), GatherContent and a whole range of CMSs. If I had any talent at all for writing fiction, I’d put in the effort to master Scrivener.

I wrote a good chunk of my forthcoming book—Screens, Research and Hypertext—with a pen and paper.

I haven’t really loved any of them.

My main beef is that they’re all built around the wrong conceptual model.

The document

On one end of the spectrum, you’ve got Microsoft Word with it’s 6.02*10²³ formatting options. It’ll produce a nice(ish) thing to run through your laser printer. But Word is notoriously bad at producing content for the web.

On the other end are all the Markdown-based apps. My own go-to is Byword, though Ulysses and iA Writer suck most of the air out of the room. These minimalist writing tools focus on producing clean markup for export to blogs and websites and the like. Most of them offer various “distraction free” modes.

You can write an amazing blog post or article with these apps. Only a psychopath would draft book in iA Writer.

The trouble is that both the simple markdown apps, the complex desktop publishing software and all the things in between are still aimed at producing the same kinds of writing we’ve always done.

“But Joe,” you say. “Isn’t blogging younger than some of your millennial colleagues?”

And that is true. It would be a good counterpoint were it not for two important facts: (1) Montaigne invented the essay in the middle of the 16th C and (2) a blog post is an essay that happens to be published in HTML.

A new kind of writing

I’m not here to bury traditional writing. Print is an extremely effective medium and it’s given rise to some incredible genres. Indeed, I prefer to read nonfiction on paper, and I’ve gone through about a novel per week for most of my adult life.

I love print. I do not love slapping print things on the web.

Because the web isn’t print.

• Hyperlinks mean that users can choose their own path through content.
• Databases mean that the same piece of content can be presented in multiple contexts simultaneously.
• Structured content management systems allow us to encode the function of different text elements using words rather than relying solely on formatting.

Very few writing tools make it easy to write this way.

There are some. Our friends in the technical writing community have been doing a lot of these kinds of things for years, built on the backs of XML-based component content management systems. Those work really well for highly structured content like recipes or technical manuals—content that has fixed (and usually unvarying) patterns.

They’re not so great at producing, say, an historical analysis of the War of the Roses or a baseline economic forecast for the 118th Congress.

Toward a new breed of writing tools

One of the things that makes writing so hard is that our writing tools expect a nice orderly argument, but our brains don’t work that way. We jump around! We chase tangents! Take flights of fancy, leaps of faith and other motion of abstract concept metaphors!

In ye days of olde, research required a lot of index cards. You write one idea per card, then start arranging and rearranging them until they start to resemble something you can turn into an outline. (Or that’s the method we grumbled our way through in high school, anyway.)

Scrivener—a polarizing writing tool geared toward longform fiction authors—explicitly adopts the notecard idea as an organizing principle. (And by explicitly adopts I mean is a skeuomorphic nightmare with fake corkboard and pushpins and curled edges.)

Others like Notion and Craft adopt a different metaphor—an infinite canvas that allows authors to add content and notes in multiple dimensions, move bits around, and draw arrows and various connectors between ideas. Even Microsoft is getting in on this particular trend, with Loop, a canvas onto which one can bring snippets of live text from other Microsoft apps (including Word).

Then there’s the set of so-called “personal knowledge management” tools like Roam Research and Obsidian. These center bidirectional links, using a wiki-style syntax to make it easy to link individual concepts and to autogenerate listings of the different pages on which that concept is discussed. Additionally, they make each paragraph of text individually addressable, opening interesting possibilities for embedding sections of text on multiple pages.

Writing is not publishing

One caveat: these are not publishing tools.

Most bill themselves as either project management (Notion), collaboration (Loop, Notion) or note-taking (Craft, Roam, Obsidian) tools. And while Scrivener bills itself as an authoring tool, most of its users seem to export drafts to Word once they reach a certain stage.

That said, you can force some of them to be. I’ve published a book using Roam Research. It made for a wonderfully liberating authoring experience.

Žiga Kropivšek, Ben Bastow and Graham May—my brilliant Soapbox colleagues who bravely designed and developed around Roam’s limitations as a publishing platform—have at various times been of a mind to drown me in the Thames. (And, honestly, the person who thought Hiccup was an improvement over HTML syntax…you should go have a think about what you’ve done.)

But, whatever their limitations around publishing content, each of these tools frees us from the tyranny of the printed page, offering an opportunity to write in ways that are possible only in a digital context.

I encourage the research community to dive in. Don’t limit yourselves to a tool that was itself limited by paper. Try some things. Find one that works the way your brain does.

Even if it’s the thing from Microsoft.