Writing tools for the wandering mind

long-delayed Day 15 of #100DaysToOffload

As a (now former) professional academic and (still now) amateurish writer of everything from code to web copy to short story and translation, I have spent far too much time trying out various text editors, writing tools, note taking apps, and systems. I suspect it is a fault of personality (no, scratch that, it is surely a fault of personality) that I can't let something be. I gain some comfort from rearranging the furniture in my office, from periodically refreshing some of the tools I use, and from seeing if some other set of writing workflow wears a bit more comfortably under the fingers. I suppose I'm always slightly uncomfortable in my own skin. I can't change that wholly. But I can try on some new clothes.

Don't let me give the impression that I am flitting from one thing to another. I have a decade-plus commitment to plaintext going. My current writing toolchain reflects that. I find that such things work great for short and small. It's when you get to the more serious levels of organization that I start to have some trouble. There's a burden to organize in some way. I've tried obsidian and zettlr and the notetaking tools. And they're pretty good. I have this back of the mind thought that maybe if I just invested more time in setting up some workflows in there that I'd get more out of them. And that may well be true. But then the cost of doing that kind of organizational maintenance runs up against the reality that life is short. And thus a cycle continues.

I've been thinking therefore about how I work when I'm most productive. What is my best case organizational scheme actually like. It was sobering, if not a bit distressing, to realize that I'm a paper-gatherer and pile-maker. I like to gather things in giant heaps. Drafts are stacked one on top of the other. I take them and cut and rearrange as huge physical chunks when necessary. I read and absorb things fairly rapidly, such that I don't really want to externalize the cognitive alchemy all that much. I want to pour it out onto a page with regularity and then be able to arrange and fashion the pieces.

And that's where I run into trouble. There is an easy way to organize piles of things, with things at top and bottom, with a stack of a certain size, with things that are clearly printouts of articles taking up space in a different way than my own drafts and iterations.

Technology flattens. Things that are distinct in other contexts or outside of a computer become the same kind of object. E.g. images, text, movies, all become kinds of files. Text objects, more specifically can be big or small and where they would take up physical space that makes this distinction clear, in most platforms they are all equal. You can't see at a glance that one document is a behemoth and the other is a wee snippet. Perhaps you make tags or color code to do this, but now I've simply invested time to hand decorate what is an already self-evident feature of the material itself.

I suppose one reason I enjoy most tools which do one thing well is because they self-consciously homogenize. Write.as, hedgedoc, various “focused” or “distraction-free” text editors all allow you to produce a stream of text. It's simple, it's straightforward. It is a somewhat more pure object than what Word or a word processor does. What you then do with that text document is entirely up to you. I have yet to find a way of handling those documents that doesn't flatten everything. (Yes, I know, Scrivener, etc.... Let me emend: I have yet to find a non-overwhelming way of handling etc.) I thought for a while that I could use note-taking apps this way, for tagging and organization. And, sure, that kind of works. At the least, I appreciate how I can keep everything in my plain text filing system and deal with it in a notetaking app or in vim if I so choose.

I'm not seduced by the idea that if I only had the right tool then it would be possible. I tend to obsess more about how the tools we use impact the way we work and the way we feel. I don't feel good using a bloated tool. I suppose I have an old and naive notion, both as a formerly professional academic writer and as a presently minimally publishing everything else writer, that writing is pleasure. It is a joy in my day. So maybe I'm particularly sensitive to tools that foster that vs. those that don't, and ways of working that are enjoyable enough that I can push forward for hours vs. those that feel like the machines I'm using are torturing me.

I have long been a fan of Peter Elbow for helping students push through their writing hangups. Freewriting tends to inoculate against many common student writing maladies; it is especially effective combating high-school-itis, an unfortunate condition whereby students have become brainwashed into thinking that five formulaic paragraphs of pablum are what every teacher wants to read. (The truth is, alas, that such artifacts are simply cause for deep sadness and regret that so many students have been tortured into thinking that this is the end point of their writing.) But in the long term, the organizers often win out. And it is that line that so many software products tend to take. It is practically a mantra of current tools for helping writers to suggest that outlining or character organization or some other form of planning is the proven method. I suppose that's why I always feel alienated by those sorts of tools. Their emphasis is on putting the planning into the software, as all software must by nature be carnivorous of data. It's not merely that I don't want to feed the tool. I'm pretty content to do my organizing elsewhere, in notebooks and blank sheets. Those physical tools have the advantage of speed and low barrier to entry. They have disadvantages when things start shifting around, when plans change perhaps, or when keeping track of many projects that intersect with one another.

I suppose then that's where I'm heading. What sorts of tools can serve the wanderer? We have them for the individual document. But what about when we want to string those documents together into something larger, from a blog post or pamphlet to a short story to a guidebook to a novel or a series of novels in a vast world. I think I want that sort of tool. It's not an organization tool. It's not even a tool to track drafts or compare things. It's more like a map, where I can plot changes ahead, keep track of my path, and explore areas I didn't know I wanted to go.

Apropos of nothing, this is long-delayed day 15 (which, I know, should really be sequential rather than having weeks and months between them) because I've spent the summer retooling, taking a radical off-ramp from academic life and into tech fully, if not full-time. More management than coding every day, but by necessity as much as by choice.

Maybe it's time I build what I'm after.

After I go for a walk.