How Bear Manages Tags Without Getting Messy
Bear takes a different approach to tags than most note apps, and honestly, it feels more like organizing files in Finder with colored labels than using a traditional category system. Tags in Bear are just text you type anywhere in your note — stick a hashtag in front of a word, and boom, it’s now a tag. For example, typing `#clientA` inside a meeting note automatically files it under that client. You don’t need to go into a separate tagging menu or remember to fill out metadata fields.
The cool part is nested tags. You can create `#work/clientA` and `#work/clientB`, and Bear treats them like a collapsible folder tree in the left sidebar. It’s like building your own custom hierarchy without touching a settings panel. I found myself building a main tag like `#projects/active` and then breaking it down into sub-tags for each job. You can also rename tags instantly by just editing the hashtag text in one note — Bear updates it everywhere. That’s something I kept forgetting Evernote definitely does not do without opening a dedicated tag manager.
But here’s the one frustration that bit me: Bear has zero tag suggestions by default. If you don’t remember whether you wrote `#finances` or `#finance` last week, you end up with two different tag lists and notes split between them. I actually had a note disappear from my normal search results until I realized I’d spelled the tag wrong. The only workaround is to habitually check the sidebar before adding tags, which is slower but keeps the chaos down 😛
If you’re coming from Evernote, you might get thrown off by the fact that you can’t open a tag and drag notes into it. You have to edit the tags inside the notes themselves. This sounds like more work, but in reality, it makes your tagging more intentional. Still, sometimes I wish they just let you drag-and-drop on busy days.
Evernote Tagging System And Where It Breaks
For years I thought Evernote’s tag system was untouchable, but then I actually started tagging hundreds of notes and ran into the strange lag that creeps in when the tag library gets too big. Tags in Evernote are kind of like a database table — they exist separate from your note text. You can’t just type a hashtag anywhere like in Bear; you have to apply them in the note’s tag field. The nice part is you get tag suggestions as soon as you start typing, which reduces those duplicate-tag accidents.
Nested tags exist too, but they’re purely for organization in your tag panel. They don’t function the same way Bear’s do in search. In Evernote, if you tag something as `Clients/Alan` you can’t find it by searching `Clients` alone unless you explicitly add that parent tag to the note as well. This drove me slightly crazy because in my head nested tags should be a built-in hierarchy.
There’s also the clunky “Tag Manager” window, which feels like software from ten years ago. Editing a tag name here changes it everywhere, but you have to dig three menus deep to even get to it. A small but consistent annoyance is the inability to mass apply tags from the main tag list — you have to select notes first, then apply. That’s two or three clicks more than I want to deal with when processing a big batch of meeting notes.
One other quirk that caught me off guard: sometimes the synced web version of Evernote will temporarily forget tag associations after a large offline batch edit. They usually come back after a full sync, but the first time it happened I thought I’d lost half my organization system 🙂
Exporting From Bear Without Losing Structure
Exporting from Bear feels slick at first because it throws you a buffet of formats — Markdown, plain text, PDF, HTML, and even DOCX. But here’s the catch: Bear treats tags as in-text hashtags, so depending on what format you pick, they may or may not survive the trip. Markdown keeps them intact, which makes it great if you’re planning to import into another app that recognizes hashtags (like Obsidian). PDF will show the tags visually, but obviously, they won’t be clickable or functional.
For bulk export, Bear has a “Select All Notes” option, then you can hit Export and choose a folder destination. The tags will still technically be there in text form, but you lose the sidebar tag structure because it’s just a text export, not a database transfer. I learned the hard way that if you were relying on the nested tag grouping, you’ll need to recreate it in your new tool.
One thing Bear does really well here — and this is underrated — is preserving inline images with your export. In Markdown, it puts all the images in a separate folder with correct links in the files, so your notes don’t look like Swiss cheese when you open them elsewhere. Evernote’s export tends to dump massive ENEX files that other apps can’t read without conversion.
Evernote Export Limitations And Workarounds
Evernote gives you essentially one real export format: ENEX. This is an Evernote-specific XML format, which makes it great for backup but painful for platform switching. ENEX keeps tags, attachments, and formatting, but almost nothing else reads it natively. If you want plain Markdown, you either need a converter script or a third-party service. That means an extra step and usually some cleanup after import because Evernote embeds weird XML meta comments in the text.
Even stranger is what happens when you export multiple notebooks at once — it merges them into one giant ENEX file instead of separate files. That’s fine for backup but annoying for migration. If you’re exporting for a move, it’s usually better to do it notebook by notebook so you can keep structures somewhat intact.
Images and PDFs usually survive the export fine, but embedded audio often ends up as separate file blobs you have to relink manually in other tools. And while ENEX keeps tag associations, those tags are stuck as plain text in the XML, so new apps will treat them differently depending on whether they fully parse Evernote’s format. In some cases, they end up inside brackets or prefixed wrongly.
Ironically, the clearest use of Evernote export is when you’re exporting to… another copy of Evernote. Anything else feels like you’re breaking open a locked suitcase with a butter knife.
When To Start Over Instead Of Exporting
There’s a point where exporting is more hassle than rebuilding from scratch. I hit this when trying to move five years of Evernote notes to Bear. Between the ENEX conversions, the broken nested tag logic, and the inline tables that fell apart, I realized it might be faster to just pull out only what I actually still use. I ended up copying my key notes manually, retyping some outlines, and leaving the rest archived in Evernote as a cold storage backup.
If you’ve been tagging inconsistently for years, exporting just brings all that inconsistency with you. For example, in Evernote I had near-duplicates like `tax`, `taxes`, and `tax-year` — and guess what, they all imported into Bear exactly as-is, making the mess even bigger because now they’re mid-sentence hashtags.
A surprisingly clean method for migration is to use your old app as a reference library while you rebuild the important notes in the new one with fresh tags and improved structure. It feels slower but you end up with a more usable system that actually makes sense.
How Sync Behavior Affects Tags And Export
Something you don’t think about until it goes wrong is how sync timing can wreck tagging. Bear’s sync through iCloud is almost invisible — it just happens — but that also means if you bulk edit tags right before closing your laptop, they might not finish pushing to your phone. I’ve opened Bear on mobile the next day and found half my notes missing tag updates until I forced a refresh.
Evernote’s sync has a more obvious progress indicator, but it’s possible to cause merge conflicts if you edit tags on two devices before they sync. Instead of losing tags, Evernote might duplicate the whole note with different tag sets. This gets especially bad if you export right after such a conflict, because the export will contain both versions.
If you’re planning a big export, it’s worth doing a full manual sync first and then checking both desktop and mobile to see if your tags actually match.
My Personal Take On Which Is Better
If all you care about is lightweight tagging that you can see right inside your note, Bear wins hands down. It’s fast, clean, and the nested hashtags look great in the sidebar. Exports are also human-readable without special software. But if you’re in an ecosystem where tag suggestions, bulk editing, and data backup matter more, Evernote’s heavier system might feel safer.
I honestly keep both running — Bear for personal ideas and writing drafts, Evernote for long-term business records. The truth is, exporting between them is never perfect. You’re always going to lose some structure, and you’ll probably discover a few duplicate tags you didn’t know existed until you see them side by side.
For what it’s worth, if your system breaks often like mine, you get faster at just rebuilding it instead of fighting with exports ¯\\_(ツ)_/¯