Trying iA Writer

In the past few years I’d been doing most of my writing in a combination of Bear and Ulysses. Bear for note taking and shorter form stuff; Ulysses for long form writing. Both these apps worked well for me individually, but even though I had drawn a pretty clear line between them having two different writing environments did introduce a bit of friction. There are also a few things about Ulysses in particular that rubbed me the wrong way. I dislike the non-standard way it handles Markdown links, for example.

In late 2018 I decided to give iA Writer a try. I picked iA Writer in part because of some of the things Federico Viticci has written about it. I liked the idea of an editor that stores files in iCloud Drive and plays nicely with iOS features like Open in Place. It has both Mac and iOS apps, which is a hard and fast requirement for me these days.

Moving to iA Writer

The first step in this process was to move my existing files from Ulysses and Bear over to iA Writer. Ulysses was simple, I just exported my files to iA Writer’s iCloud Drive folder and they showed up in the app.

Bear was a bit harder because it has a very different metaphor. Rather than files and folders Bear has a flat list of documents organized using tags. While iA Writer supports tags, they’re clearly secondary to the file/folder structure. iA Writer also doesn’t allow for nested tags, which I use pretty heavily in Bear.1

I decided to try to turn my Bear tagging system into nested folders in iA Writer. To do this, I first made sure that everything had a tag of some sort, then exported all of it to a folder on my hard drive. I wrote a Python script that identified the tags by looking for lines starting with a hashtag that was not followed by a space or another hashtag (which would be Markdown headings rather than tags). The script created a folder in the iA Writer iCloud Drive directory for each tag (and within each of those folders for each subtag) and copied the text files into the appropriate folders. I did have to do some manual tweaking afterwards, but I managed to translate my nested tag structure into nested folders a lot more easily than if I’d tried to do it manually.

Likes and Dislikes

Perhaps this is not very consequential, but I don’t think iA Writer looks a nice as Bear. It’s rather monochromatic compared to Bear’s nice use of accent colors.

On the functional side, I like the fact that iA Writer uses vanilla Markdown with some very lightweight highlighting rather than trying to do something fancy and different the way Ulysses does (and Bear, to a lesser extent). One area where I wish they’d go a little further with the Markdown highlighting is to do a better job visually differentiating between different levels of Markdown heading. All headings look the same, and are basically just shown in bold.

I have run into a few bugs. Most annoyingly, the iOS app sometimes freezes when I try to drag and drop text, either within the app or dragging to another app in split view. Copy and paste work fine though, and I really like the ability to move lines (or highlighted blocks of text) up and down with the keyboard. This is especially great on the iPad which lacks some more traditional text manipulation capabilities that you can do with a mouse.

It’s very common for something I write at work to start as a Markdown text document, then get exported to Microsoft Word to share with my colleagues. I like the results of iA Writer’s Word export quite a bit better than Bear or Ulysses.

I may need to rethink my organizational scheme to work better with folders. I’ve got stuff broken up into a lot of different, very specific folders, with lots of folders at the top level and, in some cases, nested quite deep. This worked well with Bear’s tagging system, but I’m not sure this is the best way to do things in a files and folder system like iA Writer’s. Thankfully, iA Writer’s file search capabilities are quite good and very easily accessible from anywhere within the app.

If I do decide to reorganize my file system that will definitely be a task to do on the Mac. Moving files within the app on the iPad is not very intuitive.

On iOS, iA Writer includes a Command Keyboard that can be used to insert common markdown tags, special characters that are hard to get to on the iOS keyboard, etc. There’s a ton of customizability behind this so you can set it up to have exactly what’s most useful to you. I particularly like the fact that it’s available on the iPad even when you have an external keyboard attached.

A change I’m going to stick with

Overall, I’m pretty happy with iA Writer. Having one app for all my writing simplifies my workflow and I like the vanilla approach to Markdown. I’ve gone ahead and cancelled my Bear and Ulysses subscriptions and at least for now, I’ll be using iA Writer as my primary writing app.


  1. A “work” tag with separate tags within it for individual projects, for instance. ↩︎