Rethinking My Note-Taking App Decisions

2025-06-14 8 min read

Intro

Over the past 48 hours I’ve once again been on a journey to rethink how I take notes. Why? I’ve actually been struggling to answer that question for myself, and I’ve boiled it down into a few potential reasons:

  • I’ve never felt fully at home in Obsidian ever since moving to it, even though I’ve been using it for over 2 years now.
  • I miss the seamlessness in my life of old Evernote, and constantly wish that there was an alternate that filled the same role in the same way.
  • I have liked Bear from the time I first saw it, and wish that I could convince myself that it fills all of my use cases.

What Do I Miss From Evernote?

I started using Evernote back in the early 2010s (I think 2014; I’ve not checked the exact date while writing this post), both as a way to store personal notes and documents, and for some work-related project notes.

The things I miss from Evernote boil down to a few key capabilities that other apps can do, but not as well in my experience:

  • Evernote was very good at parsing forwarded emails, PDFs, hand-written notes, and regular text, and quickly surfacing what I needed based on a search with a few tags. It was my single external brain, in many ways.
  • Evernote had a cloud, desktop, and mobile component, and for me they always stayed almost perfectly in sync until right towards the end. I was able to reliably switch between devices and pick up where I left off, with only a few seconds of syncing required (at least, that’s my recollection). Because of the cloud component, I could actually work from basically any web browser if I had to (combined with Todoist for task management).
  • I honestly didn’t normally feel the need to use things like backlinks, even when they became available, because a series of tags were able to succinctly tie notes together.
  • When I moved away from Evernote I felt a little like I split my brain into multiple locations. I’ve mostly gotten used to a system with multiple tools now, but it feels less natural.

Why Not Use Bear?

When I was originally looking for Evernote alternates, one of the options I ran into was Bear, and I immediately loved how capable but simplistic it was, and the amazing mobile and desktop experience. Bear is one of the most aesthetically-pleasing apps I’ve ever used, and the iCloud sync seems to “just work” every time I’ve used it.

So if I like Bear so much, why don’t I just move to using it full time? I’ve actually tried this multiple times (and did live in it exclusively for a few months a couple years ago), and during this last bout of indecision I actually tried using Bear almost exclusively for a day full of meetings. And it honestly worked well, but when I tried to move a few pieces of my knowledgebase to it I was reminded of the hangups I always run into (and I’ll document them for future-me to review):

  • Bear has no concept of a difference between a note’s title and a header, and therefore, the way my brain works, I basically can’t use H1 anywhere other than for the title. This eventually leads to me using more header levels than actually look good throughout the rest of the note.
  • Bear has a web app on the way, but no Linux app, and therefore for now all of my work has to occur on either my MacBook or iPad. I like both, but sometimes I want access on my Linux computers.
  • Bear’s tag structure is both amazing and annoying. I like being able to file a note in multiple categories, but I miss the way that notes in Obsidian (and in Evernote previously) kept the filing largely out of my way, not as part of the body of the note.
  • I wish that the note navigation (header levels, etc) were always visible while working on notes. I use that and backlinks quite often currently, and having them hidden away in a pop-up menu doesn’t work well for me.
  • Bear has decent backlink support overall, but I wish it had recommendations like Obsidian does where it surfaces recent documents you’ve been working on. Almost all of the time that I’m creating backlinks I’m referring to a note I was just editing, but I may not recall the exact name of that note (I create a lot of meeting notes for work).

What’s Wrong with Obsidian?

So why am I constantly tempted to move away from Obsidian? I think my primary problems with Obsidian are two-fold:

  • Using Obsidian Sync, I cannot access my notes from a device that isn’t syncing my notes.
  • I still do not enjoy parts of the Obsidian UI/UX, and this is exacerbated on iOS (iPadOS is in between).

Let’s dig into those further.

Local Notes + Sync

In general, I actually like having my notes stored locally. There have been a number of times over the years where I’ve lost network access during a meeting, or I’m in an area without network access (plane, rural area, etc), and having my notes stored locally and synced between devices has actually been fantastic. There’s nothing that prevents me from continuing about my business, and then syncing when I again have network access.

However, there are a few downsides to this too.

When I first go to set up a new device, I have minutes worth of syncing that must occur before I’m able to use my notes. This is a minor use case, but it’s still annoying. This also impacts my workflow slightly when I jump between devices (between computer and mobile, or computer to computer); there is always some amount of a sync required before I can begin taking or modifying notes.

Also, I have no way to access notes without syncing my notes to that device. This is very rarely an issue, but occasionally I wish I could log into a website to access my notes, instead of having to sync my notes to a computer before accessing them. Normally I work around this my only using my mobile device in such a scenario, and copy/pasting what I need to a chat app or website temporarily that I can access both places.

Now, yes, there are ways to sync between devices using something other than Obsidian Sync, and I’ve considered them, especially iCloud sync. However, from both my brief testing and what I’ve read online, Obsidian Sync is by far the best and most robust option, and neither of the above issues has been large enough that I’ve wanted to find a workaround yet.

UI/UX + Non-Native App

Over time, the Obsidian UI/UX has grown on me, but I still find it inferior to Bear in a few regards. Specifically, multi-level bulleted lists don’t render as nicely in Obsidian as Bear, and the UI has a tendency to feel more cluttered than I would prefer. Some of the clutter is entirely my fault, as I’ve chosen to use two plugins that add content to the side panels (Recent Files and Calendar), but I would argue that some of it is inherent to the design of Obsidian as well.

I’ve looked multiple times at using a different theme, and for a while I stuck with the Minimal Theme by Steph Ango (kepano), but none have to this point stuck quite as well as the default Obsidian theme. I probably could go about creating my own theme, but I have yet to be able to identify exactly what I’m looking for; I can tell that I don’t like a look and feel, but determining the why often escapes me.

Additionally, I think part of me still really likes having a native app look and feel, specifically on Apple platforms. Even though I’m typing this on my Linux desktop currently, my primary use case for a notes app is on an Apple-based device: my MacBook Pro, or my iPad or iPhone when on the go. Obsidian works well overall, but does not have the feel of a native app. Or maybe it’s the UI of a native app that I’m missing. To my point earlier, I struggle to identify exactly what bothers me at times.

Conclusion

So what is my conclusion? Honestly, I barely have one. For the time-being, I’m going to stick with Obsidian, as I have thousands of notes that would need migrated if chose a different solution, and I have yet to find anything that is a clear winner.

I will probably continue to look for ways to customize the look and feel of Obsidian to make my experience more enjoyable, and I’ll also spend some time reconsidering how I take notes. I do think that consolidating some notes into larger long-running documents will work better and help me keep from feeling like something is falling through the cracks.

And maybe I need to re-evaluate my move away from Evernote… I migrated due to some concerns of vendor lock-in and pricing, but if it solves all of my problems and the team that acquired it didn’t negatively change UI too much (which I’ve seen some online comments on), perhaps that’s the right call.