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Writing is Bad, and So Are Computers

I’ve followed the Plan 9 philosophy so far down the rabbit hole that I now understand that computers are tools, usually half-assed ones, and that basically every possible system for using them so far is merely trying to be less bad than a previous one.

I used to be an optimist about such things; I wanted to believe that the reason writing was so hard was because I just hadn’t found my tool for doing it yet. I tend to think of things in terms of systems, of technology stacks (hence the name of this website), and so naturally I just figured if I could create the right combination of software and hardware, the right workflow, I wouldn’t have so much trouble writing. Plan 9, counterintuitively, stripped me of those notions. It mostly made me understand that most software I use every day is not very good and it’s not going to solve problems that aren’t really software problems.

Writing Tools I Have Known And Tolerated

Here’s a list of all the tools I’ve used to try to write fiction in the time that I’ve been serious about it—a time which stretches back to age 16 or so. I’ve presented the list roughly the order I first used them, not the order they were released. I’ve also only listed things once; there’s a lot of back-and-forth that’s not irrelevant but also not useful or possible to catalog.

  • AppleWorks 6
  • Word 2002
  • AbiWord
  • Word 5.1
  • BBEdit 2.1.3
  • OpenOffice
  • Pages (‘05 and ‘06)
  • Nisus Writer Pro
  • Word 2007
  • Scrivener Gold
  • The original version of Ulysses that wasn’t just a Markdown app
  • Scrivener
  • Markdown text files in Sublime Text
  • Byword
  • LibreOffice
  • Word 2010
  • Markdown text files in Emacs
  • Org files in Emacs
  • Word 2013
  • iA Writer
  • Word 2016
  • Word 365
  • Markdown text files in Acme on Plan 9
  • Org files in Acme on Plan 9

There’s no way this is a complete list. I’ve been doing this too long and in too many places and on too many computers for that to be the case. I’ve also taken long detours into writing longhand with pens (cheap ones and expensive ones) and pencils (I buy more from CW Pencil Enterprise than I’ll ever use) on cheap paper and in fancy notebooks, and using my beloved Olivetti Studio 44 typewriter.

In short: I’ve tried everything. I’ve written a million words, probably, and dozens of short stories, and I’ve started probably 25 novels and finished 3-ish manuscripts. Not to mention my detour in sports media as a card-carrying member of the Professional Basketball Writers’ Association, which probably put another million words on top of that, just all produced late at night on a deadline, mostly in Markdown.

I give all of this to back up my credibility when I make the statement I’m about to make:

Computers do not make me a better writer. If anything, they make me worse. This isn’t really the fault of computers.

I am barely writing anything these days, now that I don’t have deadlines. I’ve worked on fiction, but mostly decided that I’m bad at that too. I’m sorta happy with the half-finished short novel I’ve been plugging away at for a couple of years, but progress on it is agonizingly slow and I keep constructing Byzantine new writing environments as an excuse for starting over instead of pressing ahead.

One of the best fruits of my 9front explorations has been the discovery of the work of Stanley Lieber, which has seeded a whole new interest in self-publishing for me, meaning I’m now almost totally at peace with never needing to find a publisher for my work—the need to be a validated genius-level literary something or other has mostly subsided as I’ve aged.

And yet: I’ve stripped down my process and started over too many times to count, only to always crash the same car.


The War of Art is way too macho for me, in some ways, but nonetheless I really like parts of it. I like what it’s trying to say, anyway, about Resistance, that thing that keeps You, The Writer from being able to do the work. I feel a lot of Resistance, always have, except for those blissful years in undergrad where I mostly subsisted on coffee and cigarettes and wrote piles of garbage on my HP Mininote 2133 instead of going to class.

It took me eight years to get a degree, and I mostly only learned what not to write.

But in that process, accumulating those instincts about how not to say things, reading back through drafts where the whole thing had to be thrown away and redone because I was taking myself about four times too seriously, or the drafts where nothing worked, where nothing was believable, or more often, where nothing happened and none of it was even worth rewriting.

The more times that happens to you, the better you get. I know I’m a pretty good writer—both because people have told me that about things I also thought were pretty good, and because sometimes I read back stuff I’ve written and don’t remember having been smart enough to say some of those things. Every writer who does it enough, especially one who has been in a workshop setting, develops a baseline of taste.

Along the way, though, that instinct to throw away, to start over, to tear down what’s been done because I see its flaws and think it’s not up to scratch: it’s a curse as much as it is a blessing. I’ve painted myself so firmly into the corner that I can’t even reach the brush anymore. I’ve built up my list of tricks and my list of “this sucks” so large that nothing I try can stay clear of it. Instead of embracing the Anne Lamott shitty first draft, I write a first draft and then assume that, because it’s shitty, so am I.

And you can only get kicked in the teeth so many times before you stop smiling, you know? I still want to write, and I still find myself doing it anyway, so I’m doubtful I’ll ever stop. But it gets old. The doubt introducing drag into the process little by little over the years, the creeping sensation that nothing I’ve written is actually worth anything, the fear that I’ll never actually publish anything again. Pressure I’ve mostly assumed onto myself acts as a parachute, amplifying the resistance that much more. To throw in another metaphor, the pressure I put on myself, built up over years of writing even though my writing has improved quite a bit over time as I’ve done more of it, is like putting a two-barrel carburetor on a Chevy V8. There’s only so much power you can produce when you’re not able to breathe enough air.

Somewhere in the back of my mind is also the notion that in the highly evolved surveillance state there’s no way to avoid the notion that you’re not quite free to say anything you want, knowing that Someone can check in on what you’re working on at any time. I have more thoughts about this, but none that make sense to explore in the context of this post.

So: Writing tools don’t reduce friction, but they don’t really produce it, either. They’re friction multipliers. They’re effective ways to avoid writing, and sometimes that’s their only utility.


There aren’t any, or anyway, none that I can describe here. Writing is hard.

The tools we use to do it are fine, but I wouldn’t say any of them are really as good as they could be. Every friction point bogs down a process that’s already hampered by the writer before they even fire up an editor.

I’m not sure what I’m driving at here, other than I’m frustrated again, not writing, and I’ve caught myself blaming the tools again. It’s not the tools—it’s almost never the tools. But when you’re already not in a good place to be writing, the tools will only sink you even faster. I’m not even sure this is the fault of the tools themselves; as mentioned in the first section, even pens and paper lend themselves to procrastination. The act of writing is hard, and there are no good ways to do it. You just have to wait until the pain of not writing becomes worse than the pain of writing, and hope your computer catches whatever comes out in a decent way. Some do that better than others, I guess, but right now I’m more stalled out than I’ve ever been, and I’m not enjoying it.


I’ve had a terrible time actually getting Jekyll to include this post in its compiled HTML output for this site, for no apparent reason. This is a static site generator that’s supposed to be simple; in fact, up until now I assumed I mostly understood how it worked. And now, I’ve got to figure out what’s keeping it from working the same way it always has, even though I haven’t changed anything about my configuration. The current state of most software strikes me as untenable, and the vague interactions of that brokenness with the attempts of writers to write strikes me as unexplored territory.