Since reading Tiago Forte’s Building a Second Brain where he referenced Obsidian for taking notes, I’ve repeatedly seen it mentioned far more than most other apps. It seems to be a fairly popular hashtag on Mastodon in the note-taking community. I currently use Bear and really don’t have a need to change apps, but this morning I decided to see what Obsidian could offer.
When visiting https://obsidian.md, I immediately saw it was multi-platform, supporting macOS and iOS specifically. A big plus! Like Bear and several other note-taking apps, it’s based on markdown, which would make porting notes from one application to another pretty easy. That’s something I’d want to do, if changing apps.
And the price for personal use was $0 (free!). I’m a proponent of paying for software, even if that just means donating money to support it, so I checked out the other options. I could pay a one-time $25 “Catalyst” fee and get developer-level information, but I don’t need that. And $50/year for “Commercial” use was fine too.
Because I use Bear on my Mac, iPad and iPhone, syncing notes was important too. The Obsidian page has a Sync tab at the top. Here was my first negative. $96/year to sync. Bear is free to use, but it too charges for the privilege to sync. I’m currently paying $15/year and it’s been solid. Still, price difference wasn’t significant enough to keep me from switching.
Next, I downloaded the app and opened it.

I had a few problems with this window. The biggest is that it’s dark by default. I like dark at night and low light but prefer light during the day with plenty of light. This was an easy to control setting and I could set it to my system default instead of “Dark”. My bias immediately tells me this is a “developer” choice because I see more developers who choose to use dark all the time. This is a poor default choice, which meant there could be more.
The next problem I had was all the buttons! There’s about 20 of them along the left side, at the top and even more at the top of the left pane. Tooltips made it easy to understand what some of the more obscure buttons do, but there was still too much clutter.
Similar appearance issues hit me when I viewed Obsidian’s Settings area. The interface is just clunky. I assume that’s a compromise made to support multiple operating systems. Still, when I looked at something like the Interface font option, it screams “over-developed” to me. This is the font for the Obsidian interface not new notes. Maybe this level of detail was put in for accessibility needs, but I don’t think so. There’s no option that I found to simply increase the interface font size or use system Accessibility settings. Those would have been simpler choices.
To change the Interface font also requires I click a Manage button, choose a font from a list menu and then click Save instead of just showing a simple list menu with the default font selected. Other options like Window Frame Style and Themes made Obsidian seem amazing at first until it just became tiresome to have so many options.

It’s as if the developers thought “customizability is more” instead of making better discreet choices for the end user. So far, this interface reminded me of a now defunct open-source developer IDE called Atom, which I evaluated and chose not to use for similar reasons.
My last feature to evaluate was importing my Bear notes, which are also markdown. I would’ve been pleasantly surprised to see an “Import from Bear” option or plugin, but I didn’t expect it. And there isn’t one. So, I searched online with “import bear notes to obsidian” and found a couple of community posts on the process.
The top hit seemed just like what I was needing. It suggested a few things I could do to my existing Bear notes to make them more compatible before exporting. I chose to ignore those suggestions until deciding to make the switch.
But in a few cases this post and one or two others I found were sometimes poorly worded. The first mentioned “importing” notes to Obsidian, but what I really had to do was export my Bear notes to a folder, choose File > Open Vault and then point it to my export folder. After reviewing three different articles, I finally managed to understand what I was suppose to do.
Now, I had some data to play with. I wasn’t expecting my arrangement of notes to match Bear, and they didn’t. If I were to use Obsidian, I’d have to plan for something new. Not a big deal. I would have to redo a lot of tags because while Bear allows spaces, Obsidian doesn’t. I’m pretty good at regular expressions and scripting and thought I could use those as tools.
I thought the Graph view was amazing! And I appreciated the way I could look at certain sections of my notes to identify the relationships they had with each other. I’m sure there was a more involved way I could use this, but off the top of my head, I wasn’t seeing a need that I was missing. Neat, but useful?

I’m technical enough that I could use scripting and regex and other tools to put my notes back to something very similar I had in Bear. Possibly, I could find a few tools in the available pool of 750+ available community plugins to help me. But after five minutes of simple putzing to see what was possible, I realized I’d be spending far more time that I was willing to invest right now. And still nothing gave me a compelling reason to switch away from Bear, which has an elegant interface with fewer but smarter options for customization.