Organising Writing with Ulysses

It’s time to talk about tools: I’ve been using Ulysses for all my writing for a few months, after seeing multiple recommendations and, well, never really loving the much-loved Scrivener.

If you want a basic rundown, because there are lots of tutorials and testimonials on the app’s site and elsewhere:

  • Plain-text composition with Markdown / Extended-Markdown syntax
  • Individual ‘unit’ of text is a “Sheet”
  • Sheets can be collected into Groups
  • Groups can be nested inside one another, creating a hierarchy
  • You can set word-count goals, filter, and search at any level of that hierarchy, including at the Sheet level
  • Syncs between macOS & iOS
  • Keeps incremental backups
  • Built-in support for quickly exporting text in a variety of formats, one-click publishing to WordPress or Medium

Okay. I’m going to talk about using this app for everything I want to write down, whether notes or stories. The big thing for me has been developing my hierarchy of Groups.

Groups

Here’s where I’ve landed, so far: I have a top-level “Fiction” group, and I’ll get into that in a minute. Next to it sits “Craft of Story”, which is for this blog. That’s divided into three sub-groups: “Ideaphile” (I’ve been calling my drop-box for ideas by that name for ages, and I’m quite proud of the pun, thank you very much), “Draft”, and “Polish and Publish”.

That third one doesn’t get much use, and I might bin it: once I take an idea from Ideaphile and move it to Drafts, that’s when I write the post. Once I go back to the draft to polish it, I usually just do one editing pass and then immediately move it to Published (see below), so it doesn’t seem like I need a whole group that will probably only have one thing in it at a time.

Then again, I am still trying to get my editorial calendar up and running (so I’m not always writing the thing I’ll post, deciding what it is, on the day I want to make a post… i.e. what I’m doing right now) so there might be something to drafting a bunch of posts and then leaving them enqueued to be polished and published…

Tracking Published Words

Back at the top level, I have a “Published” group. Under that, “Published in 2018”; I’m going to have groups for each year because I want to track how many words I’ve put into the world each year, not just how many words written (there are too many different ways to track how many words you write—per hour, per day, per project—it doesn’t lend itself to one master collection. Words Published is simpler that way).

Fiction

Now, a Fiction group serves as the root for fiction, both long and short. Inside Fiction I have another Ideaphile group. This is for all fiction-related ideas that haven’t yet become a project. Each project gets a Group. I haven’t done much short fiction lately, that might just get a single group for all such stories, but anything where I think it’ll have multiple chapters and have some character and world-building sheets, that gets its own Group, with an appropriate icon (because let’s have some fun).

Projects

In order to avoid over-complicating things1, I usually just dump sheets directly into a project’s group without creating sub-groups, at first. Once I start having lots of sheets of different kinds, then I’ll create appropriate sub-groups. For a novel, I’ve been following the structure outlined by my writing coach Joe Nassise in his Story Engines course, so I’ll create a group called “Scenes” that’s broken down into “Preparation Phase”, “Reactive Phase”, “Proactive Phase”, and “Conclusion Phase”, and then as I brainstorm scene ideas, I chuck them into the appropriate bucket. This makes it quite easy to see how the novel is shaping up and where I need to solidify and generate more ideas, before I’ve even started writing the draft.

Monitoring Progress

If you click a group in Ulysses, the sheets in that group are listed underneath headers for their own sub-groups. So you can get a high-level visual indicator of which groups have a lot of sheets and which don’t. Then, you can right-click the group in the group list and select Statistics, and it will show you the number of sheets in the group. So if I see that my Preparation Phase has 20 sheets but my Conclusion Phase only has 5, I know I need to do some more thinking and planning / brainstorming for the end of the book.

Still talking novels: alongside Scenes, I’ll create groups for Characters and Settings. Those will of course contain sheets that describe each important character and place as I have ideas about them. I do a lot of free-writing here. Whatever ideas for characters and places don’t come to me in the shower usually come by creating a sheet with the header “Sidekick – Talking Turtle” and then just cranking out words until a sketch of the character takes shape.

Now, then. I’ve started drafting a couple aborted novels, and will be starting one again soon (this one’s getting finished!) My plan there is to create a Draft sub-group, copy in scenes from the Scenes group, or just pin a scene in a separate window for reference, and then create a sheet in the Draft group for the actual writing. Once I have scenes drafted, I can easily move them around and combine them into chapters. The Draft group contains the thing that will eventually get edited and produced and published.

I’ll revisit that last bit once I’ve actually written the thing, because I’m sure my techniques will change in practice.

  1. I can see you rolling your eyes over there, quit it.

The Tyranny of Tools

There are lots of things you could do to ignore your writing instead of doing it, one of the biggest for me is playing with the tools. If you’re a writer these days it’s probably about apps; even if you have a vintage-looking typewriter on your desk, you hipster, you, I’m gonna guess you don’t crank out novels with it, not all of them, anyway, and if you do you probably aren’t reading this blog. So, for the rest of us, let’s just admit it: I play with tools.

I bought Scrivener a long time ago, and it’s a great app, but it’s also complicated which means there’s a lot to play with. If I spend time playing with it, on the one hand, it should return dividends because it helps me be a more productive writer… hypothetically. But on the other hand, every minute I spend in a writing app during which I’m not writing is not taking me any closer to my goals. So there’s something to be said for using the simplest tool possible.

Okay, but TextEdit doesn’t give you any kind of organization, you have to organize everything you write yourself in your filesystem. And Macs introduced filesystem-wide tagging a little while ago, which now syncs across devices with iCloud, so you could set up an elaborate series of folders and tags and apply them to all the little files you produce. Since everything would be plain text you could copy that filesystem anywhere (though the tags may or may not come along for the ride).

But in everything I just said, you didn’t see writing anywhere, did you?

Okay. So lately I started using Ulysses, which is the kind of app I like: you can use it in a simple way, but as you get more complex (goals, keywords, publishing formats) it scales up and up with you… which is useful and fun, but, again, beware how much time you spend tending your tools.

Whether a tool is simple or complex, you’re going to spend time feeding and watering it, which necessarily detracts from your writing. Yet the feeding and watering should also enhance your productivity. There doesn’t seem to be an escape from this conundrum, and I love alliteration, so I’m calling this the tyranny of tools.

I’ll be honest: I do love my tools, and love finding new ones, and will probably write about them here. And I’ll be even more honest, that’s an attractive type of content. People like reading about tools, it makes you feel productive… but that feeling, when it doesn’t translate into production, is inherently dangerous.

So my goal here is to establish The Great Caveat: if you’re reading this post, or any future post about tools, you should probably go do some writing instead. I won’t feel bad if you do, okay? Let’s just have a gentlemanly handshake and agree it’s what’s best for us both.

Rabbit Holes and Blind Alleys

There are three big areas where I reach for tools:

  1. Creating: the actual writing bit
  2. Organizing: the keeping track of what I create
  3. Publishing: ultimately the whole bloody point of this enterprise, without which, the foregoing two steps are of limited utility in the world

And I swing back and forth between two philosophies:

Having one extremely simple tool to do one extremely defined task, where each of those tools can talk to each other in a standard way, so you can find the right tool for each job, and then link them together to accomplish the Superjob. This is creatively satisfying if you’re a technology geek like me, and is also aesthetically satisfying in a way, probably for the same reasons.

But it’s fiddly. Even after you’ve found all the pieces, you still need to make the glue to bind them together, and, once again: this is not the real work you need to be doing as a writer.

The other philosophy is to find One Tool To Rule Them All, something in which you can write, organize, and publish all right there in the app. I believe the incomprehensible colloquialism is ‘soup to nuts’.1 I mentioned Scrivener and Ulysses (and will probably mention them again) and there are even more tools than those in this category. But OTTRTA isn’t a perfect solution, either, because you have to learn how this big, complex tool works well enough to use it.

Either way you go, you risk rabbit holes and blind alleys. That is, you risk spending way more time than you expected on something (the rabbit hole was deeper than it looked), and you risk trying out a tool only to discover it doesn’t quite fit your needs or wants (you went down a blind alley). Both are frustrating and expensive.

How do we avoid tumbling endlessly down a rabbit hole, which will not result in a finished novel? After all, how many rabbit authors do you know, exactly? Hint: Watership Down was actually written by a person. How do we avoid putting a bunch of time and energy and possibly money into a tool only to realize the magic was inside of us all along (or in another text editor all along)?

The same way we distracted, disorganized meat sacks accomplish anything in this vale of tears: we make a system.

Make it a System: Tool Time

I first got this idea from Curtis McHale: you set aside specific times where you just look at tools. Maybe an hour every couple of weeks, or a day out of the month, you let yourself spend all that time playing with new things, even if you’re happy with the things you already have. Now, to give us any hope of doing this efficiently, just like sitting down to write, you need to be prepared.

First, know what you’d like to check out. The way I do this is to have a running list. Whenever someone tells you about some cool tool, or you come across it on the web, or on someone’s screen when you’re spying on them at a coffee shop instead of writing, don’t go look at the tool right away. Just add it to the list. Since you know you will eventually get around to checking it out, you don’t have to keep it in the back of your mind.

When your tool time comes ‘round at last, you’re going to pick from the list, and I suggest picking / organizing the list in terms of pain; what aspect of the job are you having the most trouble or annoyance with right now, and what tools will help? If you’d like to find your favourite place to make words come out, look at the writing apps / text editors themselves. If organizing eludes you, focus on apps with a good organization experience. If you’re struggling to put words out into the world, look at publishing tools, etc.

Now, pick an app and go look it up. Maybe it’s on a website or an App Store. Before you get your hands on the thing yourself, go to their site and/or YouTube and look up reviews or videos of people using it. Watch a couple of these. If it still looks appealing, consider how it’s distributed and what it costs: does it run locally on your computer / tablet / smartphone, or is it a web application? Does it cost anything? Do you pay one time, or does it have a subscription? If it’s not free, does it have a trial? How does that work, and what happens when the trial is up? (If you put some writing in there, and don’t decide to keep the tool, what happens to the work you’ve done?)

Once you’ve answered these questions and decided you want to give the tool a try, decide exactly how. You might have a specific series of steps you try with every tool so you can easily compare them. Simple example: whenever I’m trying out a writing app, the first thing I do is put the cursor on the place where the words go and type,

I am the very model of a modern major general, I’ve information vegetable, animal, and mineral.

Aside from being amusing, this lets me immediately see what the typing experience “feels” like, what it looks like, what kind of auto-correction features it does or doesn’t have, is there formatting, how does it work, etc.

For something more complicated, like an organizing or publishing tool, you may want to have a small set of pieces you’ve already written ready to load into each new tool to see how you can organize them. Perhaps even have a ‘staging’ site where you can publish things privately just to see how a new publishing tool behaves. That’s advanced-level stuff, but if you set this all up beforehand, you reduce the depths of the rabbit holes and the lengths of blind alleys.

If a tool isn’t an immediate bust, you may want to keep using it outside of your established tool time. If so, and if it’s replacing another tool, you’ll want to have a plan. You’ll want to already know:

  • If this is a trial, how will I handle the trial running out if I choose to (a) proceed or (b) stop using it?
  • If I have a bunch of writing elsewhere, do I need to import it into this new tool? If so, how and when will I do that, how much of a pain in the ass will it be? If not, how will I keep things organized between this tool and the others?
  • If this is for publishing, how will I get it set up with all the places I want to publish? If I already have a ‘publishing workflow’, how does this fit in?

If this all sounds too prescriptive, well… like anything else I prescribe, I’m first prescribing it to myself. I try to do the above with tools, but still fall into plenty of rabbit holes and blind alleys. I’m going to continue building a system like the above, and I’m going to link back to this post—with its Great Caveat—whenever I talk about tools here. And if you have tools or a system for trying them… let’s be honest, I wouldn’t mind taking a break from the writing to hear about it. As long as I don’t stay away too long…

  1. I have no idea what this means, and I’m not sure I want to find out.