Interesting premise, and after reading, a few thoughts about it.
For one, part of the reason writing about the tech world is difficult is because it’s inherently a set of new mediums.[^1] I’m with Marshall McLuhan and that we dump out new communications mediums before we have even really finished understanding how the previous mediums worked and how they affect society and societal interactions. Writing about it is hard because a lot of it is in flux, a lot of it is new technologies that outsiders don’t fully understand (thus people who do, like Kara Swisher, naturally being insiders), and we definitely don’t understand the long-term effects on human communication and society.
The internet exploded when US society was still dealing with the implications of Cable News and the 24-hour news cycle and “If it bleeds, it leads.” We hadn’t and still haven’t solved those issues or even attempted to address them. How can we expect to effectively discuss it in a world that still barely understands the implications of radio and television and while the internet/tech is still in many ways nascent technology despite maybe 70 years of tech growth? I don’t think we can and there are a dearth of writers like McLuhan around today to write about the tech sphere and its monopolies.
Further, as posited in the article, some of the best writing about the tech world and the internet is often not about it at all.
I myself would peg Guy Debord’s Society of the Spectacle as an early work that exhorts many of the philosophical ethos of the early open internet/underground internet/punk internet and modern meme culture and culture jamming in general. Prescient and profound to the modern moment, in my opinion, especially the re-surging Piracy and media-preservation movements.
“The spectacle is not a collection of images, but a social relation among people, mediated by images.”
I wonder how Debord would feel about individuals becoming part of the Spectacle, partaking in the act of mediating their social presence via images? That’s the simplest explanation of modern online profiles of individual people, that they are a marketing “brand” for the individual in a world increasingly dominated by Spectacle and Hyperreality.
[^1]: McLuhan would argue that something like the invention of the lightbulb spurred creation of new mediums. His example was an after-dark baseball game. Previously, the bleachers would have been empty and dark. After electric light, a baseball game could be held at night, creating a new medium. I say collection of mediums because while the internet is a backbone of multiple mediums while self-driving vehicles creates spaces for communication there previously were not similar to the baseball game example. This is my personal opinion and admittedly weak understanding of McLuhan.