Writing Bear just gets me

300 Times a Day

When your favorite software tool receives a major update, it’s all dread. It’s not you expect them to ruin the application (although possible); it is because it’s your favorite tool, you know all the intricacies of how it works, and you know exactly how you need it to work.

This is not a casual tool. This is crucial. This is a piece of software you use 300 times a day, which means one subtle, seemingly meaningless change could ruin your workflow forever.

I use Bear 300 times a day. Probably more. I could sketch their five preference screens from memory. I’ve written and edited two books in Bear. I’ve spent hours understanding how tags propagate through the system. Ask me about their sync system. Quiz me on their keyboard shortcuts.

When the update landed earlier this week, I held my breath for five minutes straight. The Verge article claimed a “rewrite from the ground up1,” which sets the stage for a worst-case scenario for a critical tool. I fired up the updated app and watched them migrate my thousands of notes for a few seconds. The window appeared, and my first delicious thought was, “Wait, what’s different?”

Thank god.

Much is Different

My first reaction2 was the best because Bear is my home. It’s not a place I occasionally frequent; it’s always open. It’s where articles begin and finish. It’s where I capture random bad ideas. It’s where the first drafts of complex emails are created. I’m a word guy, and this is my word place, so a “nothing’s changed” first impression on a “rewrite from the ground up” narrative is a comfortable starting point.

At the core of my love of the Bear is a line from an article on How to Write a Book: “Features create choice and choice is a dangerous distraction, and the last place you want to find distraction is in the tool you use to write.”

I began my exploration of Bear 2 within the preferences; first noticing was that there were fewer preferences. Same number of sections, but less choice in each section. Less choice, yeah, you read that right. I want talented designers and engineers to make choices for me. I want them to do this because I trust their judgment, and I don’t want to spend my time fussing with knobs and dials in my favorite tool; I want to spend my time writing. Tinkering with a tool isn’t productive; it’s procrastination.

This is the core of my dread. I need application owners to continue demonstrating incredible product judgment so I can use the tool and not worry about how the tool could work.

Bear 2 continues to demonstrate fine judgment.

Nips and Tucks

Given it took seven years to get a major revision to Bear, it seems disrespectful to call the set of changes I’ve noticed nips and tucks. There is confirmed a considerable amount of engineering and design that went into Bear 2, but as noted above, they’ve made these changes subtle and unobtrusive.

BearSansUI Within the editor, the first and most noticeable change is Shiny Frog introduced BearSansUI (and BearSansUIHeadline) as part of this release. This default new font replaces Avenir Next. It also accompanies a significant typography change for the product in that you can use any typeface instead of six in the original version of Bear. But why would you not stick with BearSansUI — a typeface designed specifically for Bear? I don’t know. I trust the experts.

Here’s a comparison of BearSansUI with Avenir, which I suspect is its core inspiration:

BearSansUI:

Avenir Next:

My go-to letter of comparison for typefaces is the ampersand. Go compare. The BearSansUI ampersand softens a complex swishy character and makes it calm. You can see this intent in capital Q, as well.

Bear has always supported Markdown, but my impression is the developers picked and chose the parts of the fractured standard that suited them. As a non-power user of Markdown, this didn’t annoy me because I’m not tinkering with Markdown; I’m writing. For Bear 2, Shiny Frog now adheres to the CommonMark standard, which is “a strongly defined, high compatible specification of Markdown.” This will please the standard folks but mostly means my highlight syntax changed from :: to ==.

More important to Markdown is Bear added a preference to Hide Markdown. Enabled means that once you’ve finished bolding or italicizing a bit of text with the appropriate formatting, the markdown vanishes, leaving you with styling. Markdown purists may take issue with this because they always want to see the formatting, but I love this option because writing a piece involves an entirely different part of my brain than editing.

When I’m writing, I need as little distraction as possible; I need to get the words out. I do Markdown, but asterisks, octothorps, and other formatting text are visual noise. When I get to publishing the piece, yes, show me all the formatting details because I need to see these details to edit and format it properly, but when I’m in the zone, I need sweet, sweet, cleanly formatted words.

Bear 2 also introduces a formatting toolbar that allows you to do formatting, insert todos, and, as a new feature, tables. I’ve tinkered with the new table feature briefly, and it’s impressive. It gives you all the necessary options to add, remove, and move rows and columns, and copies in various formats (Markdown, CSV, and HTML). Still, I wonder how many folks are keen on littering their beautiful text with tables. I’m a sample of one, but in my extensive usage of Bear for seven years, I have never not once considered adding a table to my documents.

I won’t be a frequent user of the formatting toolbar because if my hands leave the keyboard, well, I’m not writing.

Additional observations:

  • My impression is every bit of artwork, like the typeface, has been either replaced or touched up.
  • Bear has three views: edit, notes, and editor and notes, editor, and tags. I swap between editor (focused) and editor and notes (organizing). The note view has been visually tightened up and now includes options to sort this list and adjust the preview style. Use large. Turn it off when you don’t need it. You’re welcome.
  • Bullets now indent text as opposed to outdenting in Bear 1. I didn’t know how much this bugged me until I created my first bullet in this version. Bullets also follow CommonMark rules and can nest blockquotes and titles.
  • Footnotes are now also supported. No clue how these behave when exported to publishing platforms.3
  • Sync continues to just work. This is an invisible but essential feature because Bear is vital to all my Macs, iPhones, and iPads.
  • There are six additional themes. I am frequently theme-changed-based-on-mood and am delighted to have more moods.
  • Finally, a dedicated panel within preferences to select your app icon. This seems like a waste of real estate until you remember I’m the guy who changes his template based on his mood.

What you are reading is my first significant piece of writing completed in Bear. The next step will be passing it through Grammarly to tidy up grammar and spelling. I will then post to WordPress. These final production steps might teach me more about Bear 2, but I doubt my opinion will change significantly:

  1. Solid update. Didn’t adversely affect any of my writing workflows.
  2. Intense attention to detail. They took a significant risk introducing a new text and headline typeface, but it’s instantly appealing and gives a subtle application more personality.
  3. My bar for paying a monthly fee for an application is high. Bear 2 greatly exceeds that bar.

301 Times

My final compliment for my favorite applications. When these applications release anything, I first pour over the release notes to read what has changed. When I’m done with that, I walk through the entire application, every menu item, every preference, and everything I can click to see how the documented changes work and discover undocumented changes4, which always exist and often surprise.

Yes, it starts with dread, but that rapidly turns to joy and hope because these applications are my favorite because I’ve learned designers and engineers just get me.


  1. I pinged the developer regarding why they did a rewrite. They have a forthcoming version of Bear for the web, and the most performant strategy was building C++ compiled to WASM. The web version has yet to be released. 
  2. This article was written and edited entirely on the Mac. I haven’t evaluated the iOS version of Bear 2. 
  3. Let’s find out. Just works with my WordPress setup. Sweet. 
  4. I keep the prior version of the application around — network disabled so it doesn’t update — as a means of comparison. 

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5 Responses

  1. Nathan 7 months ago

    > I first pour over the release notes to read what has changed

    Because this is a homophone that bugs me, I have to flag it (and feel free to ignore me). You pore over the release notes. If you poured over them, they would get wet.

  2. Great review: short, pointful, and hitting solidly on real world usage.

    Re. footnote 4: how do you keep the prior version of the product. I wish I’d done that.

  3. Jennings 7 months ago

    Great article. I’m going to give Bear a try. Thanks!

  4. Ann Chen 7 months ago

    What a great review! I totally agree with you, if you don’t really notice any big difference after a big rewrite, it’s absolutely not a bad thing. I can’t imagine how much time and efforts Bear team put into it to make it simple and elegant as usual while packing with 20+ new features. Bear app is a real art.