Hi everyone. I’m looking for one recent time when working with local files made it hard to get back to a task.
I’m building Voyager, a macOS file manager for knowledge workers who lose time finding and reusing files.
Right now it’s a native file browser where folders, AI chat, and other work pages can stay open together. You can talk with the files you’re already looking at, and pin the setups you expect to come back to.
Over time I want agents and more automation on top of that, so getting back into the real task is faster than rebuilding context every time.
I’m collecting recent examples of those stuck moments so I know what to focus on first.
I’m running a short survey about one of them: what you were trying to do with the files, what made that harder, and how you handle similar work now.
It takes about 3-5 minutes, and you can answer the main questions without entering your name or email.
At the end, you can choose whether you’d like a 7-day Voyager trial code.
I’ve always added a minute or two to every task session for file management, and never get lost wondering where “X.pdf” went to. I never accept default names for file saves, and stick to a structured naming convention that’s served me well for decades. It’s just a useful, low-overhead work habit.
Otherwise, I’m not sure what itch your app scratches.
I took a peek at Voyager’s web page, and I’m not sure I have a clear picture of what it actually does. It looks like it creates something akin to a saved search called a “Collection”—is that correct?
That could be a useful tool, but perhaps not in the way you intend it. I wouldn’t use it to solve a disorganization problem—I’d use it on a project by project basis as an alternative to linking to documents stored in different locations via a tool like Hook. (I index my Finder folders in DEVONthink databases and use DEVONthink links pasted into a project-specific markdown document to give myself ready access to files I might need.)
Re the “Chatting with your documents” angle: When I need to work this way—i.e., with Finder folders in the left pane, a document or documents in the center pane, and (in my case) Claude Code on the right, I just use VS Code. Note that this is for knowledge work, not coding. (VS Code comes with a markdown editor, a PDF reader, a browser, plus a ton of plug-ins.)
So, to do something like your first example, all I’d need to do is open my downloads folder in VS Code. I’d get a file list in the left pane, a center pane where I could open one or more documents in the downloads folder, and Claude Code in the right pane. I could then ask Claude to do something with the downloads folder—review it, organize it, delete duplicates, whatever.
I’ve attached a screenshot for whatever value it may have.
Thanks Katie. It sounds like you’ve got a solid routine that works.
Even with a good system, is there anything about the file manager itself that slows you down?
Would automating any of that routine be useful, or does it feel like the manual habit is part of why it works?
You’re right. Collections are essentially saved searches. But, what I’m aiming for is something like what you’ve built by combining VS Code, DEVONthink, and other tools, but integrated into a single file manager. I want to build a smarter file manager where you can browse, read, and work with AI agents that have the context of your files.
That’s why I’m running the survey. Honestly, the solution is still somewhat fuzzy, so I want to understand where people actually feel friction in their work.
Your setup is clearly working well, so the questions might not be a perfect fit. But hearing how someone with a mature system thinks about this is genuinely very helpful.
Showing my age here, but your headline sounds like it’s straight out of the Lennon/McCartney songbook (in a good way).
That said, my main challenges with file management stems from working across large teams with non-existent corporate governance or guidance on tool usage. A document or file can be found anywhere across a multitude of locations, so the pain is real.
I long for the day when I can consider productivity tooling in the context of my own needs and preferences, but as that day will only come after retirement. I hope I won’t need a lot of tooling in addition to simple, old-school practices like consistent folder structures, good file names/ meta-data and Spotlight searches.
