I think you might be post-hoc rationalizing an emotional feeling, as clearly this meme is emotionally triggering to everyones nostalgia/pessimism nerve (hence why it went viral).
I'm 100% positive more people would guess the far left icon is a text editor compared to the far right icon. Not that I like the left icon aesthetically. Both are pretty weak icons.
Leftmost is probably a pen, rightmost is definitely a pen and specifically a fountain pen. I've never seen these icons before, and I'm trying to be the fairest I can, and I think rightmost wins at evoking "text editor". But the one exactly in the center wins by a mile. Pen on lined paper, hard to do better.
Same thought.
The one on the left just conveys "notes" to me. Middle actually seems to be about a more "well put together" document. A fountain pen by itself doesn't necessarily mean documents to me, but signing them.
I'm 100% positive more people would guess the far left icon is a text editor compared to the far right icon. Not that I like the left icon aesthetically. Both are pretty weak icons.