search technology, in particular, seems to have failed us. Searching the Internet and our personal computers peaked sometime in the mid-2010s and has become steadily worse (witness Spotlight and it’s Linux and Windows counterparts). Contextual and topic searching has become “premium”. Finding an e-mail in your native language about taxes in 2016 would be impossible if, well, it wasn’t in “Personal/Finance/2016” — because there is just no way I can tell Siri (for instance) to find it for me, even if it was written in English.
And that’s the _easy_ part. Photos are a problem, too. I have an offline copy of everything filed by date, but have tried iCloud, Google, OneDrive, etc. Tagging people in photos is a challenge, and having weird, creepy “memories” reminders from any of those services popping up unprompted (and often mis-matched) makes me think nobody cracked that yet.
I do believe that we can do better than plaintext notes, but (at least so far) Zettelkasten and Obsidian aren’t it, either (I don’t get why Obsidian doesn’t leverage standard front matter, for instance, or why folder names can’t really be used as namespaces).