A late night with a Bear
(A different Bear.)
It was last night at 10:15 PM. My wife and I were watching an episode of Catastrophe (fun show) until she began falling asleep. At this point, as per protocol, I typically shut the laptop and go to bed myself. But instead, on a near-whim, I ran down to my basement office, installed Bear.app, and started dumping my Obsidian notes into it.
Why would I do such a thing? Why, when I’ve decided time and time again over the years to stay with Obsidian, admonishing myself to resist the temptation of the shiny alternatives? Why, when, as a middle-aged man, an hour of sleep has the approximate value of the eternal soul of my first-born child? These are dang good questions that I was asking myself up until 12:30 when I finally crept back to bed, head spinning.
Background
I was an avid Bear user once upon a time. I loved it. But I was also susceptible to New/Different/Shiny Syndrome back then. I tried Notion, Org Mode, and probably some others I’ve forgotten. Then Obsidian became the new hotness with its backlinks and extensibility. I hopped on the bandwagon.
I kept Bear on my radar, however, especially as the team was releasing the 2.0 editor in 2023. More recently, after I got back into blogging and reading others’ blogs, I saw Bear crop up on various blog posts, like this one. I started Googling “Obsidian vs. Bear” more and more often. Down the rabbit hole I went.
Why
Bear 2.0
When Obsidian came out in 2020, it felt like a leap forward in evolution compared to Bear. But in 2023, Bear released version 2, which brought many new features (backlinks!) and leveled the playing field. Without that release, I wouldn’t be considering this move.
Simplicity
Over the past few years, simplicity has become a core value of mine. When choosing among competing tools without an obvious winner, I try to choose the simplest option. The purpose is to reduce the cognitive load of my tools, saving me energy and time over the long haul.
Obsidian is not simple. Its fundamental design assumes extension through plugins. Even the core features are not just builtins — they are “core plugins”: backlinks, bookmarks, command palette, quick switcher, etc. This means there are quite a few configuration options out of the box, even before you get to the 2,112 community plugins and 310 community themes you can choose from at the moment.
To many of us nerds, this extensibility is the appeal. I used to feel that way. To many others, it gives Obsidian too much complexity and too steep a learning curve. I don’t mind the learning curve. In fact, I rather enjoy it, just as I enjoyed going deep on Vim and Emacs in years past. But the complexity carries a cost. There’s a reason I don’t use Vim or Emacs anymore.
With Bear, you get what you get. It’s all out of the box. You can tweak your typography, pick a built-in theme, and change the app icon. That’s about it.
This means there are vastly fewer choices to make with Bear. Sure, there’s also much less flexibility than with Obsidian. I can’t use my favorite editor shortcuts in Bear, for example. I can’t use Dataview to query my notes like I would a SQL database.
But I see this constraint as a feature in itself. It means I spend more time focused on my content than on my editor. It means I become more adept at the macOS defaults rather than whatever cocktail of customizations I’ve thrown together on a whim. It means I’m forced to keep it simple. In turn, all of this means reduced cognitive load and time lost.
Beauty
Beautiful apps are calming, I find. This is why I’ve used Things as my task manager for as long as I can remember. Its beauty makes the chore of task management more peaceful.
Bear is arguably a beautiful app as well. Beauty seems to be a core part of the team’s design philosophy. Indeed, “beautiful” is one `of the first words on the app’s landing page.
Obsidian, on the other hand, is arguably a bit … funky looking, and it gets funkier the more plugins you bolt onto it. The typography, spacing, and UI decorations aren’t beautiful out of the box. You can customize all of that, of course. But it requires side quests.
Take another example. Obsidian Outliner is a very popular plugin that makes Obsidian feel more like a first-class outliner. It mostly works fine. But on a somewhat regular basis, it renders something a bit off. The spacing between a bullet and the first word is wonky, or the cursor gets stuck in a list item and refuses to respond to a keyboard shortcut to move elsewhere.
These quirks are easily forgivable, as these plugins are built and maintained free of charge by the community. But the lack of seamless beauty is distracting. It increases my cognitive load by making me wonder if it’s somehow user error, by making me question whether I should still use this plugin despite the bugginess, or just by being a mere annoyance.
Also, not to be a party pooper, but much like browser extensions, each one of those community plugins is a security risk. My company actually has a policy that Obsidian plugins need to go through internal code review before they can be used. That’s annoying but it makes sense.
In sum, to answer the “why” question: Bear seemed to win the simplicity and the beauty contests. These are things I care more about now than when I first started with Obsidian. This, combined with having had a great experience with Bear in years past, was enough for me to justify giving it a proper go once again.
First impressions
Pros
Migration. It was pretty easy! (If it wasn’t, this experiment would have ended quickly. I’ve done heavy notes migrations before and am not interested in another one. Moving out of Notion was the worst.)
Bear has an import handler specifically for Obsidian, which imports titles and tags nicely.
When you import a batch of files using that handler, Bear applies the #obsidian tag to the imported notes.
So, for example, I could import my journal/2024 notes, select them all under the #obsidian tag, and then batch apply the #journal/2024 tag to keep them organized similarly.
Then I’d delete the #obsidian tag to clean up before the next batch.
It took maybe 20 minutes to go from “I have no idea what I’m doing” to “Oh hey, I think I’m done!”
Simplicity. I covered this above, but it’s worth repeating. Obsidian has overwhelming potential for customization and configuration. Bear is underwhelming in that regard. And that’s a good thing for me.
Mobile apps. Bear has great iOS and iPadOS apps. Obsidian’s mobile apps are fine, but a bit cluttered and awkward to use. I’m embarrassed to say I still don’t know how to trigger quick-open on Obsidian’s iPad app.
Sync and onboarding devices. Adding Bear to a device is dead simple. You just install it from Apple’s App Store, open it up, and it starts syncing immediately. I assumed I’d at least have to log in or something, but nope. It just goes!
Obsidian requires several steps before the sync machine starts moving. You have to manually connect to each cloud vault, enter your encryption password for each vault, manually enable sync for each vault (though I think they just today released an update to enable sync by default), and then sync tool has about 15 additional settings to manage.
Bear was such a breath of fresh air in this department.
Native. Typing feels snappier in Bear. I could be imagining this, but Bear is a native app while Obsidian is an Electron app, so it wouldn’t surprise me if it’s true.
Also, Bear supports macOS’s built-in typing suggestions and Apple Intelligence features. Those don’t appear in Obsidian. I assume this is also because Bear is native and Obsidian isn’t.
Tag-based organization. I like Bear’s nested-tag approach to organization. I’ve always liked it. It obviates the question I have in Obsidian of whether I should be using folders on disk in addition to tags.
Today. Bear has a view that shows you only the files you’ve modified today. There’s a keyboard shortcut for it. I expect to be using that a lot.
In Obsidian, you need a plugin or your own custom script to search across recent notes. I scripted something up in Alfred to show a list of recent files sorted by modification date. It works fine, but it’s another thing to maintain.
URL paste. If you paste a URL into a Bear note, Bear automatically fetches the page title and turns it into a Markdown link for you. No plugins required. Handy!
Photo support. Per my recent post on journaling with photos, I’m hunting for an easy way to use photos in my notes. Bear has nice photo support with draggable resizing and such.
To be fair, Obsidian can also handle photos. But it’s clunky to resize them (you have to do it in the markup), and I have to decide how to organize the files on disk. There’s a config option for that, of course. I once again like that Bear removes this decision from my plate.
Export. I tried exporting a big folder of my notes to see if it’d work in a pinch. At first glance, the output looked the same as the Obsidian notes I’d imported. That made me feel better about committing to Bear’s database versus Obsidian’s pile-o-files approach, which I do like.
Web clipper. Bear has mature web clippers. Obsidian recently came out with an official one, but it choked when capturing a cooking.nytimes.com recipe. That’s my most common use case. Bear’s clipper did a great job the first time.
(Obsidian’s might have improved since I tried. I haven’t checked back.)
Shortcuts and x-callback-url. Bear has extensive integration with Apple Shortcuts. I haven’t explored this yet, but it should give some good opportunities for automation.
It also has sophisticated x-callback-url handling.
I used it to build an Alfred workflow to create a new journal entry with the ISO date in the title
and a journal/{year} tag.
It worked perfectly.
Constraint as a feature: vaults. Bear doesn’t let you have multiple vaults. In Obsidian, I have separate vaults for my general notes / PKM, recipes, and music notes. That creates significant overhead when setting up new devices, keeping keyboard shortcuts and plugin configs in sync across the vaults, creating hotkeys to quickly access each vault, etc.
Of course, I could keep everything in one vault in Obsidian, but that’s yet another decision to think through with various pros and cons. I like that Bear forces my hand. I’ll throw everything together, organize it all by tags, and be done with it.
Constraint as a feature: keyboard shortcuts. Bear has thoughtful and opinionated keyboard shortcuts that cannot be customized. While I was momentarily annoyed that I couldn’t change Bear’s default shortcuts, I quickly decided that this constraint was a feature. It means I have many fewer decisions to make.
Constraint as a feature: no plugins. Bear has no plugins. I wish I could get back the many hours I’ve spent trying Obsidian plugins that ultimately didn’t work out. I appreciate not having the choice to begin with.
For example, I’ve had a task on my list for months to explore the myriad options and shortcuts in the enhanced quick switcher plugin I was using in Obsidian. I happily deleted that task after moving to Bear.
Reasonable subscription. I know many bristle at the idea of paying an annual subscription for an app. But for my notes app, which is so core to my daily existence, I want the company behind it to have a sustainable revenue stream.
Bear is $30/year. Let’s be real: that’s flippin’ cheap. I’m genuinely glad to pay it to help keep the team fed.
I’ll note that Jason makes some good points to the contrary in this post.
Cons
Less control. My data now lives in a database instead of a bunch of text files. That means I have less control. I can’t batch operate on my text via the command line or in my code editor. It’s a tradeoff that I don’t love. But it’s been rare that I’ve really needed the control I’m losing, so I’m okay with it.
No version history. If you pay for Obsidian Sync, you get a month of version history for all your files (or 12 months if you pay up for Sync Plus). That’s comforting! I’m typically a staunch proponent of using version control systems wherever possible.
That said, in my several years with Obsidian, I’ve never once needed to revert back to an older version of a note. So, while I’m not happy to lose the feature, it seems foolhardy to call it a deal-breaker.
Bear has a backup command that exports everything into a zip file. I’ll run that every few days. It should suffice to prevent any major data loss.
No Markdown image embed.
I started adding a bunch of photos to my Obsidian journal entries
using the Markdown image embed format: .
Bear doesn’t currently support that.
Bummer.
No aliases. I’m tempted to file this under constraint-as-a-feature, but I do like Obsidian’s ability to add alias titles to my notes. It lets me create more ways to find things when I can’t remember the exact title. On the other hand, it adds some complexity in the markup when linking to a note with its alias title. I can live without it.
No properties. I’d started putting tags and other things in Obsidian’s properties, which are basically a UI around yaml front matter. It can be nice to keep some of that stuff out of the body of the note, especially when copying and pasting a post into Bear Blog!
Mac only. I know this is a dealbreaker for many. For me, it’s a minor inconvenience. I’ve tried leaving Apple’s walled garden a few times over the years. I always come crawling back. I’m an Apple guy. I’ve made my peace with that.
Conclusion, for the moment
Switching notes apps is a big deal for me, and I was quite dubious of my late night, impulsive dive into Bear. But so far, it’s feeling like it could be a great move.
Finally, kudos to Obsidian for being an excellent app that’s served me well over many years and many thousands of notes. It remains a very cool piece of kit that I appreciate deeply.