In more detail, here's a paragraph-by-paragraph "map" of the essay:
• [1–2] Three quotes that speak of cleverness negatively. So is there something wrong with being clever?
• [3-4] Connecting cleverness to being an "outsider". [IMO the main theme pervading the whole essay: alienation/dissociation.] The four character types [mentioned above].
• [5–9] The detective as outsider. [Raymond Chandler, Chinatown.]
• [10–13] The comedian as outsider. [Woody Allen, Seinfeld]
• [14–16] The flâneur (with link to detective).
• [17–19] Online cleverness (with links to the observations made about the earlier types).
• [20–22] Three paragraphs of conclusion: Kierkegaard and a way out.
In light of this, this essay is far more methodically structured than most I've read! From your comment it sounds like you're most interested in the "comedian" bits (paras 10–13 and 19), but the rest of the essay is quite connected too. And the journal is subtitled "Critical Reflections on Contemporary Culture", so it makes sense that there are references to contemporary culture.
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.
The OP gestures towards a thesis ('here's why society's championing of cleverness is bad') and then spends paragraphs meandering around it.
I think the piece does resound a bit if you can clean off the gunky verbal tripe and look at what they’re trying to say. There’s a definite problem regarding people trying to be clever. I’m just not convinced that’s the source of the problem. Just a symptom.
The point of citing Kierkegaard is to make use of the insights of others to try to explain something and to shed light on it. What the author is examining starts as a vague, confused, and murky impression that requires refinement, analysis, and effort to get to the essence of the thing. Clarity is not a given. Do you presume to know all there can be said about a thing? If not, then looking at what others have said is an opportunity to grow in wisdom and break out of the provincialism of one's own limited perspective, if only by the very act of wrestling with their material. I thank the wise who came before me for showing me the way and enriching my understanding of reality.
Is talking about "culture" a way of lumping fiction and reality together? Fictional always-right, wisecracking detectives aren't real, but there are real detectives, and presumably some clever ones whose actual cleverness is of real practical use. Fictional scientists who are more passionate than logical aren't real, but there are real scientists, whose cleverness is presumably valuable. Realistic work of professionals doesn't make for good reading. Fiction is entertainment in the first place.
There's meandering with multiple sometimes subtle qualities along the way and there's ... meandering.
Yet another funny thing occurred to me: I'm not sure I'm enjoying much non-technical non-fiction. Is Bret Devereaux[0] technical? Well, τέχνη, the root word hints at craft, art or skill. The articles focus on the "how to" (move armies, organize settlements or even write better fiction) merely using "how it was" as a teaching aid and inspiration. So the conclusion would follow that all kinds of guides are technical.
Then if a published piece of writing is neither technical (guide / manual) nor fiction (art) - what is it? Isn't it just... data?
But I do notice that HN tends to have a hard time with/disparage writing that doesn't state a clear thesis and move towards it directly. Writing that makes its point "between the lines" or through braiding apparently unrelated thoughts together and expecting the reader to finish the splice are not well received here.
I also think that, like consuming only social media probably atrophies your attention span, reading only "direct" prose atrophies your ability to experience the ride of other styles and receive what they have to give.
And again I don't really intend this as a value judgement. Both styles have their place and there is no moral imperative to enjoy all approaches to writing. But having a limited palate accidentally, being blind to that, and thinking the fault is entirely in anything that lies outside of it is in a very literal sense pathetic. And here I often sense that it is perceived as virtuous distance from foolishness instead.
I think that reaction's a combination of that sort of writing sometimes being amateurish wankery poorly-imitating better writers with better ideas, and an awful lot of tech- and science-nerd sorts having decided around 5th grade that they were already expert readers and literature and language classes were just a bunch of time-wasting made-up bullshit that couldn't possibly teach them to be better readers or writers. "It's this entire field that's wrong, not me!"
Poor literacy is almost as prevalent as poor math skills, folks are just less comfortable owning up to it. Plus a lot more people overestimate how good they are at it, I think, than do with math skills.
If an article is nonfiction, then get to the point and stay there, dammit.
I think part of the issue is that these kinds of essays serve both as an argument and jumping off point for discussion, but also as a form of entertainment. If you enjoy the entertainment, you might enjoy the argument being padded and meandering. But if you're mostly interested in hearing the argument and responding, this type of writing can fell like it's intentionally wasting your time.
I actually agree with you that more reflection in general is a good idea (though I don't necessarily agree that these kinds of essays engender that kind of reflection, but that's a separate topic). However, the online communities that exist now are designed to dissuade people from doing anything (reflection, research, editing, etc.) that take more time.
It's also the case that time is limited, and there are some topics we don't want to spend much time on. It's common to see people argue that if you don't spend as much time on the topic as them, then your opinions on it aren't as worthy, but I can't really agree with that. It's very often used as a way to defend poor beliefs against obvious criticisms. You see it a lot with conspiracy theories. "You can't dismiss this unless you've read all of the writings on it!" But only true believers are going to subject themselves to dozens of books on a crank theory.
In today's writing, perhaps because we demand so great a volume of it, purposeful prose financially rewards the author's extra effort less than ever before, and is less appreciated by readers because they're less willing to pause their pace of consumption to reflect on subtleties and unobvious insights. The online written word has evolved into a 24x7-driven ehpemeral commodity, where cleverness alone is the desiderata that makes or breaks the work and its auteur.