I actually thought it was very tightly structured: early in the essay (fourth paragraph) it sets out four character types ("the private detective, the comedian, the flâneur, and, most recently, the social media poster") and then proceeds to dwell on each of them in turn, in orderly sequence.
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.
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.