First impressions with Ulysses

In anticipation of maybe possibly hopefully having a book come out at some point, I’ve been refreshing my website. Partly because having a book might mean more people looking at my website, and partly because working on a book inspires all sorts of productive procrastination.

In collecting things to feature on my homepage, I was disappointed with how few good bits of relevant public writing I had available. There’s some good stuff, sure, but not as much as I’d like, and it’s all mostly about content strategy. I care about content strategy but it’s hardly my only interest. So I find myself chasing a vague impulse to blog more regularly.

New impulses mean new apps, of course. I’m trying to do more work from my iPad, and went looking for an app to help me develop ideas into drafts and drafts into finished pieces; a writing environment with a workflow focus. The first one I found to check most of my boxes was Ulysses.

I was initially skeptical of the library model — I’m used to keeping separate files for everything. But after clearing out my txt folder recently, I realized that hasn’t really been helping me get work done. I read through all of their guides and downloaded the trial and played around a bit and was impressed enough to subscribe. It’s not cheap but if this ends up helping me produce more work $40/year will seem like a steal.

I like that it has an inbox and I’ve used that already to good effect. I had a few text files on my work computer, which is synced to a different iCloud account, that I wanted to get into Ulysses. I used the macOS share menu to AirDrop them to my phone. A couple quick taps and there they were in my Ulysses inbox. Nice.

I was also skeptical of the Markdown-but-not-Markdown syntax, but the guides cover this pretty well. I ran a few experiments and it all exports very cleanly to standard Markdown. Works for me.

Though I haven’t used it much yet, I like that it has a notes feature. This allows you to add a note about a draft right next to the draft, but not in the draft. It’s similar to how notes work in GarageBand and Logic, a feature I use regularly in those apps.

The style and customization options seem generous without being overwhelming. I’m running in dark mode with the solarized theme for the editor. Very plain and clean but it looks kind of future-y and fun on my iPad, which I like.

Keyboard commands are not quite intuitive for me yet, but they seem reasonable.

This will be the most intense use I’ve made of iCloud and I’m apprehensive about the syncing and backup. I lost several hours of work a few weeks ago to Notes and iCloud making a whole bunch of stuff just evaporate. So fingers crossed.

I wish the version control was more robust but it’s definitely a step up from having to go to Dropbox on the web when I screw up something in a text file.

The organization scheme is making a lot of sense for me. “Groups” are the top-level mechanic, which work like folders. I added top level groups for my website, talk abstracts, and 7×77. I tried out a few options for sub groups but after watching this video from Shawn Blanc I borrowed his idea and made four sub groups under each:

  • Ideas – Stubs, brain dumps, and drafts in progress that I’m not sure I actually want to publish. Stuff that I might still conceivably use in a piece.
  • Development – Pieces that are clear enough in my head that I think I can get them done. For the newsletter, this also contains placeholders for editorial decisions even if don’t have an outline yet; e.g. I know the subject for issues 76 and 77 already.
  • Staging – Stuff that’s production ready. This is a to-do list, basically.
  • Archive – Where I’ll move stuff after staging, and where I’ll hide old brain dumps that didn’t make the cut but might be useful again some day if I change my mind.

I also like how Shawn handles research and book notes Ulysses, but for now I think I want to keep my Ulysses library focused on “stuff I am actively trying to turn into public writing” and leave Bear for “lists of interesting things and notes I want to reference”. I don’t want or need a list of my past addresses in Ulysses, for instance, and not every book quote I save is research for something particular.

I wrote this whole post from coffee shops on my iPad in Ulysses, so we’re off to a good start!

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