On tags over folders

4 minute(s)

Every few months I used to try to organize my Spotify library. Create a system. "This time it'll stick." It never did. Playlists quickly become stale as I forget they exist. Incomplete as I add new songs and fail to add them to specific playlists. The same songs would end up duplicated across tens of playlists. And over time, eventually devolved into a hodgepodge of very different “types”, across genres, listening environments and intentions, and other “ways of organizing”.

Eventually I’d stop using them entirely until the next weekend “I should organize my music” moment hit.

Playlists fail because they are folders. And folders, despite being the dominant mental model for practically every digital interface (browsers, operating systems, Google Drive, etc.), are a deeply limited way of organizing things.

The problems with folders

Designed for mutual exclusivity: A file can only live in one folder. So you're always choosing: does this song go in "chill" or "study music"? Does this note belong in "work" or "ideas"? The answer is usually "both." But folders don't let you say that. Your only options are duplicating the file, folders, or creating shortcuts between them, and now you're maintaining multiple copies of the same thing.

Nesting diminishes scannability: Deep hierarchies become opaque quickly. You end up with a graveyard of nested folders nobody navigates, including you, OR folders with hundreds of files, which is equally unusable. The deeper the structure, the more you forget what's where.

Challenging to reorganize: Once you've committed to a folder structure, changing it is painful. Moving files means updating paths, breaking links, and going through each folder step by step. So the taxonomy you picked in a hurry three years ago becomes permanent by inertia, even when it no longer matches how you think, work, or listen.

Tags, the superior mental model

Tags elegantly solve all of these issues while bringing powerful new capabilities to the table. They don't require a plan, just label things as you encounter them.

• find a relaxing song you like? tag it "chill"
• realize it's also good to listen to while working? add "work"
• later notice it's instrumental? add that too

No hierarchy. No moving things around. The organization emerges from use, not from planning. This matters because it means the fundamental organizational unit is much more flexible and dynamic. But the real benefits start to emerge when you layer on boolean logic. Folders give you one operation: "show me everything in X." Tags give you:

• AND: chill AND instrumental
• OR: focus OR deep-work
• NOT: NOT rap

And combinations of the above, such as “(chill OR rnb) AND NOT rap”.

You stop browsing and start querying, giving you a layer of flexibility that was not previously possible: both in how you find, and how you update. If your preferences change to only want instrumental music when working, you can search for “work NOT instrumental” and then untag “work” from all the results. Now your organization has completely updated to your new preferences. In a folder-based world, you had to go into your “work” playlist, and manually remove every song that was not instrumental, and you had to worry about what other playlists to add those songs into if you still liked them and didn’t want to lose them all. Tags more closely matching our own natural ways of thinking, and how that thinking might evolve over time.

Applying tags to Spotify with tagtun.es

I got frustrated enough with Spotify (and AI has gotten good enough) that I vibe-coded a solution. Tagtun.es connects to my Spotify account and replaces playlists with tags:

• all my liked songs and existing playlists are imported
• I tag them, and have a Tinder-style “speedtagging” tab
• AI can also suggest tags to speed up the historical backfill
• I can then create “taglists” (saved boolean queries)
• these taglists sync back in realtime to Spotify

It's not a Spotify replacement, but a layer on top that lets you navigate your library the way tags-over-folders suggests you should. Unfortunately their API restrictions are limited so to use the app yourself you need to generate your own developer API key. You can find instructions on how to do that by visiting the homepage (linked above) and pressing “b” on your keyboard.

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While this is a solved problem for me for music, I think the pattern generalizes. We’d all be better off with this mental model across most things: tasks, files, emails, etc. In fact, I struggle to think of even once case where folders are better. Tags more closely matches how we think about things and recollect them: contextual, overlapping, and always evolving.