It is meandering, but that's a good thing so far as I am concerned. It's an essay in the old-fashioned exploratory Montaignian style where the journey matters as much as the destination, not the sterile persuasive plod of the modern style.
The OP gestures towards a thesis ('here's why society's championing of cleverness is bad') and then spends paragraphs meandering around it.
If the author stuck to just dissecting only Twitter or Seinfeld or Kierkegaard or Einstein using some supporting of details derived from just one of of those references, or even tied in one extra reference for robustness, that’d be great in my opinion. But this essay reads like it was constructed from a bunch of transcluded notes from an Obsidian vault or a zettelkasten (where reference upon reference can be taking due to bi-directional links between notes).
I can go as far as to say that this is less classic prose, than it is prose in the manner of a Family Guy episode.
No, although that's an excellent book. I'm referring to the essay-writing tradition that started with Michel de Montaigne (who first used the word 'essay' in that sense). He was a skeptic and thought of essays as wandering and exploratory, not probative.