Ellen Ullman, has compiled a series of seventeen mostly witty, sometimes snarky,* often insightful essays about the intersection of technology and life. Life in Code: A Personal History of Technology (2017) [link].
I particularly liked the earlier essays about “The Programming Life” in the 1990s, in which she explains tech and illuminates the social realities which programmers (particularly female programmers) faced, and probably still face.
Her social critique of the internet is also spot on, as she describes the searcher’s hopeless search, “adrift in a sea of empty, illusory, misery-inducing choice.” p. 89.
She sounds almost prescient as she writes (in 1998!):
Before the advent of the web, if you wanted to sustain a belief in far-fetched ideas, you had to go out into the desert, or live on a compound in the mountains, or move from one badly furnished room to another in a series of safe houses. Physical reality—the discomfort and difficulty of abandoning one’s normal life—put a natural break on the formation of cults, separatist colonies, underground groups, apocalyptic churches, and extreme political parties.
One point she circles back to from time to time is the way the internet removes the intermediaries from our decisions, stripping out those who “traditionally had been involved in  transactions—even librarians and journalists—[but who were now seen as] incompetents, out for themselves, dishonest, the next thing to snake-oil salesmen and mustache twirlers. The intermediaries were useless; you could trust only websites; go directly to the internet.” p. 297. This “disintermediation” has brought us closer to a kind of freedom which often just leaves us adrift. GOTO p. 89.
*”Microsoft, as ever, was last in invention but first in its ability to out-market its rivals.”