My Favourite Writing Apps, Part I: Ulysses 12

When it comes to writing apps in the Apple ecosystem, I feel spoiled for choice by Ulysses 12 and iA Writer 5. They’re both great on a technical and aesthetic level, and I’ll admit to have spent (wasted?) a lot of time moving my work back and forth between the two apps, because each one has been tempting in its own special way at various points throughout my writing career.

This close competition is distracting, but it’s also a good problem to have. The folks at iA are not afraid to question their own design decisions and rewrite the app, if it just feels better as a result. There was a version called iA Writer Pro that faultered by adding extra file formats and a very convoluted system for editing, writing, and taking notes. But iA Writer 3, 4, and 5 have hit the mark by concentrating on being a lean, mean, writing machine.

But the developers at Soulmen haven’t been sitting on their heels either. They’re constantly iterating on Ulysses as a writing environment, with great a implementation of drag and drop arriving soon after iOS 11’s release. Whereas iA Writer famously removes choice with a shut-up-and-write mentality, Ulysses approaches writing as an interior designer would. Ulysses knows that the choice of colour, font, and even spacing is a very personal affair — and there’s nothing quite like the feeling of getting things set up “just right”, and then drifting into work in a digital nook that feels totally your own.

I’ve owned multiple versions of these apps for years, but this first post will be a quick recap of their strengths as of November 2017.

The last time I used iA Writer was in v4, but they’ve literally just released iA Writer 5 with some fantastic new iOS shortcuts. I haven’t spent much time with this version yet because I want to approach each of these apps one at a time, and provide them with the thinking room they deserve. Ulysses recently released a major update (v12) and a switch to a subscription format earlier this year, and although its incredible feature set entice me, the prospect of yet another monthly payment has me feeling cautious.

My plan is to dedicate a few weeks of use to each of these apps. Part 1 (what you’re reading now) is about Ulysses 12 after a good five weeks of use. Part 2 will cover iA Writer 5, and Part 3 will conclude which of the apps I’ll choose. I’ll be updating each post with links to other parts of the series as I publish them.

Overview of Ulysses

What I like most about Ulysses is that it’s mainly a Markdown editor, but with extra conveniences for writing for the web. This means that most of my work is still in plain text “sheets”, which I can quickly format in Markdown syntax. Ulysses also provides in-app niceties like a Typewriter Mode and customizable fonts, and its sheets enable embedded images, as well as a sidebar for adding metadata to individual sheets.

Navigating Ulysses is really about spending time in four sliding panels: Library, Sheet List, Editor, and Attachments. These panels are organized horizontally, so it’s very easy to visualize where you are in the app at any given time.

There are actually two panels for Favourites and Preview, but I think of them as subsets of the Library and Editor respectively.

The Library + Sheet List

The Library is Ulysses’ built-in file manager, which organizes all your text as sheets and folders. Ulysses can store sheets in iCloud or in a local “On my iPad” section. There’s Dropbox sync too, but files synced over Dropbox are really just plain text, without any accoutrements.

Organization can be simple: you keep sheets in folders, and tapping on a folder will display its Sheet List. But you can also get fancy, if you want to. Each sheet supports keywords, so you can filter a Sheet List with hundreds of sheets, just by entering a keyword or two.

If folders and keywords aren’t enough, all versions of Ulysses have a Quick Open menu that functions as a universal search. You can search for folders, titles, and even body text. This search is extremely fast, and search results show the sheet name + search matches. Calling Ulysses’ text recall features ‘comprehensive’ is an understatement. Quick Open is an incredible feature.

Another great touch in Ulysses 12 is a focus mode for the Library. You can swipe right on any folder to instantly hide all other folders, which helps to hide a lot of visual clutter.

The Editor

The writing experience in Ulysses is customizable and comfortable. You can choose from a variety of built-in fonts or import your own fonts directly into the app (Tip: AirDropping into Ulysses is the easiest way to do this). The choices don’t end there either. You can also play with line and paragraph spacing, as well as paragraph indentation. It’s not so deep that you’ll spend an hour on setup, but there’s a lot of room to make Ulysses feel like your own mythical text hero.

Ulysses also supports Typewriter Mode, which has become a necessary feature in any writing app I adopt. Typewriter Mode has a few options, but the way I have it set up will highlight and center the line that the text cursor is on. I love this because I can keep my eyes in the same place, without craning my neck downward as I write. I just keep my focus on one part of the screen and the text reflows around where I’m typing.

Ulysses does have a dedicated Preview pane that you can use to preview and export files in various formats, but I only tend to use this when I’m done with a file. Otherwise the Editor pane does a fantastic job of showing me text, links, and even images (as of Ulysses 12) in-line with live Markdown formatting.

I like writing in Markdown because I can get a lot of formatting done without ever taking my hands off of the keys, but Markdown can often look messy, especially with long links and image references. Ulysses cleans all of that plain text nicely with editable hyperlinks and image previews.

If I want to do a little more planning, I can bring up the Attachments pane by swiping left, or pressing Cmd + 4 on my keyboard. This pane is where you can add keywords, but I barely ever need to use them because the folders and Quick Open feature are already so good.

Instead, I use the Attachments pane for setting a word goal for the sheet. If I really want to do extra preparation, I’ll also place an outline in the Notes section of the Attachments pane. However, the notes are still a hit-and-miss feature for me because I find the font too small to read comfortably. I’d love the option to increase the font size of notes in Ulysses.

The last thing I’d like to mention is the extensive keyboard shortcut support in the iPad app. I write most often across the MacBook Pro and iPad, and the keyboard shortcuts stay consistent across both of those apps, so it’s always very easy to manipulate text and jump to the right file. A huge round of applause always plays in my head when I find developers that treat iOS as full-fledged companions to Mac apps, and Ulysses does this wonderfully.

Subscriptions and Plain Text

There are really only two things that give me pause about using Ulysses: the sheet format itself, and the subscription pricing. But I really do mean pause here, because neither of these things are dealbreakers — just the biggest points for consideration.

Ulysses’ sheets, as evidenced above, are quite a capable custom format. They’re mainly plain text, but dressed up for conveniences. It isn’t necessarily logical, but there’s a part of me that likes having my writing in malleable plain text files. This means that I can track and find individual files outside of the app, and I can use the text anywhere — it’s just a matter of interpreting the way they’re written (in Markdown). That said, it isn’t hard to export sheets as plain text from Ulysses on the Mac. But it is one extra step removed, which is what iA Writer spares me.

The decision to turn Ulysses into a subscription service also has me thinking about investing further in it, or making myself beholden to it on a perpetual basis. I think the subscription model makes sense for the Soulmen and the rate at which they release updates does make it seem worthwhile, but I also like the idea of owning some of the core software that I use.

This is in light of already paying for subscriptions for:

  • syncing my notes (Bear)
  • streaming my music (Apple Music)
  • managing my family’s passwords (1Password Family)
  • storing + editing my photos (Adobe CC + iCloud Photo Library)

Ulysses isn’t less deserving of my subscription dollars, it’s just later to the party. Each additional subscription I add is bound to face increased scrutiny before I’m willing to commit. feeling inundated by subscriptions. Ulysses has to feel more than just “great” for me to subscribe, it has to feel essential and offer features that I can’t do without.

At this point, I’m not quite there, so I haven’t taken the plunge on an annual subscription, even though they do provide a generous discount for existing users. The required subscription in Ulysses is why I’m checking out iA Writer 5 — which is still a completely standalone app — next.