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I’m building a macOS file manager around context, not just folders

Over the last few weeks, I’ve been writing about how people don’t really remember files by structure, and how context tends to shift over time.

Working through that, I started questioning something more basic.

What if the problem isn’t just that folders are too rigid?

What if the idea that a file should “belong” to one place is wrong in the first place?

Most file systems force a file into a single path.

But in reality, a file rarely has just one meaning.

It can be part of a project.
It can be reference material.
It can become relevant again later for a completely different reason.

The file doesn’t change.
The context around it does.

That’s the direction I’ve been exploring with Voyager.

Voyager is a macOS app I’m building to rethink file management around context instead of location.

Instead of putting files into folders,
it treats them as a set of attributes that can reflect different contexts at once.

Collections aren’t static folders.
They’re dynamic views built from those attributes.

If something matches the conditions, it shows up.
If the context changes, the view updates.

So instead of organizing files once and maintaining that structure,
you define what matters and let the system keep it up to date.

I’m also exploring how this connects with AI.

Not just for searching files,
but for actually working with them, organizing them, and acting on them in context.

It’s still early, but this shift has been interesting.

Less about putting files somewhere once,
more about keeping them connected to what they mean over time.

If you’re curious, I’ve been sharing more here:
https://voyager.fm

Curious how others think about this.

Does it make sense to treat files as something that belongs to multiple contexts,
instead of forcing them into one place?

on April 15, 2026
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    The idea that a file should only 'belong' to one path is such a legacy constraint. Moving toward dynamic, attribute-based views feels like the first real upgrade to file management since tags, especially with AI handling the contextual heavy lifting.
    Since Voyager is rethinking such a core experience, you should enter it into this competition; “Prize pool just opened at $0. Your odds are genuinely the best they'll ever be.
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    1. 1

      Appreciate the kind words. The AI layer is where it gets really interesting — not just finding files, but understanding why you need them at a given moment. Lots more to share soon.

      1. 1

        Thanks Wonsik! Glad the AI layer resonates — the contextual heavy lifting is where the real magic happens.

        Quick overview of Tokyo Lore: It’s a paid ideas competition where people submit Tokyo-connected business or creative ideas. For $19 you get a custom AI-generated artifact of your idea + a full SPEAR business analysis, plus entry into the round where the winner gets a real trip to Tokyo (flights + hotel booked by us).

        Prize pool has started building — odds are excellent right now while it’s still very early.

        Would you like to submit an idea? Happy to send you the direct $19 link and walk you through the whole process (very quick).

        1. 1

          Thanks for the offer! I’ll pass on the competition for now. Pretty focused on shipping Voyager at the moment. But if you have thoughts on how you’d want file management to work differently, I’d love to hear that.

          1. 1

            otally fair — makes sense to stay focused on Voyager.

            On file management, one thing I keep running into:

            → it’s not about storing files, it’s about finding the right file at the exact moment you need it

            A few directions that feel interesting:
            • context-aware surfacing (show files based on what I’m currently working on)
            • recent + relevant > folder hierarchy
            • lightweight linking between files (so they don’t live in isolation)
            • fast “drop + retrieve” without needing to organize upfront

            Basically less “where should I put this?” and more “it should show up when I need it.”

            1. 1

              Totally agree with this.

              “Less where should I put this?” and more “it should show up when I need it” is very close to how we’re thinking about Voyager.

              The part I’m especially interested in is making that context reusable, so it’s not just one-time search, but something you can come back to as part of a workflow.

              Appreciate you sharing these thoughts.

              1. 1

                “Yeah, making context reusable is where this really gets powerful.

                Right now most tools solve:
                → “find this once”

                But what you’re describing moves toward:
                → “bring me back to the state of thinking I was in”

                That’s a big shift.

                Feels like a few interesting directions there:
                → saving “contexts” (not just files) as reusable units
                → lightweight timelines of work (what led to what)
                → and maybe even “resume mode” for projects

                So instead of reopening files, you’re reopening momentum.

                If that clicks, Voyager stops being file management and starts becoming workflow memory.

                Also — this kind of behavior is exactly what’s hard to validate in isolation, because it only shows up over repeated use.

                On Tokyo Lore, we test tools with a small group over real workflows and see:
                → do people come back to the same context
                → what actually gets reused vs forgotten
                → what makes it feel like “infrastructure” vs just a tool

                Since you’re exploring reusable context (which is a deeper behavior shift), this could be a really interesting fit to validate.

                Happy to share more if you’re open 👍”