One of my favorite apps is called "Keep or Sweep". All it does it show me a random file (maybe one I haven't opened in a while) and ask me if I want to keep it or not.

I love it! I wish there was something similar for the desktop that would go through my old files and that it would ask me if I wanted to move the file to somewhere else, to help me keep my files organized.

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Really the core issue is also that the home directory filesystem idea is a bit silly by design.

Per application files (think executables and dotfiles) don't need to really be managed by external applications- they take care of themselves.

Files we do use between applications (documents, photos, etc.) aren't well organized in a simple hierarchy. Good indexing systems (tagging, full text search, etc.) is much better for such files.

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