I keep hearing / seeing references to “classic” novels, nonfiction works, etc. related to tech culture. I’ve read a ton, but there are always things I’m missing. Like today I heard somebody mention “A Fire Upon The Deep”. Apparently it’s a classic, but I’ve never heard of it. So onto the reading list it goes. 
If somebody were to ask you for a short list of “the classics” of tech culture, fiction or nonfiction, what would you put on that list?
I think one of the classic’s is Tracy Kidder’s The Soul of a New Machine. The story of the creation in the late 70s of a Data General mini-computer. (Not what you think of as “mini” today.) I read this in grad school and it heavily influenced my career choices. The technology is ancient, but the story of team work and competition is just as fresh today.
Another outstanding work of non-fiction (or maybe it is speculative fiction – hard to say) that still resonates in modern culture and technology almost 76 years later, is Vannevar Bush’s As We May Think. The ideal “Memex” device that Bush envisioned as a store of all knowledge is still an unachieved goal that influences a lot of software and hardware design today.
The third recommendation is Alan Turing’s Can A Machine Think, in which Turing outlines the problem of what came to be called the “Turing Test” to prove if an machine can be deemed indistinguishable from a human mind. Again, 70+ years old but an essential foundational reading for anyone interesting in why tech today is what it is.
Finally, almost in response to all the above, consider Jaron Lanier’s You Are Not a Gadget, which speaks for itself.
No matter the field, reading original sources rather than someone’s interpretation of the source is essential. If you have the time and inclination, consider a membership in the Association for Computing Machinery, and one or more of its SIGs. ACM has been the locus for computing theory for decades.
For fiction works I would add Snow Crash and Cryptonomicon, both by Neal Stephenson, and Neuromancer, by William Gibson.
The Shockwave Rider by John Brunner is a fiction classic and the origin of the “worm” term in networks.
The Cuckoo’s egg is also a good read. It’s a non-fiction book about the early days of hacking.
+1 on The Cuckoo’s Egg.
Definitely ‘The Cuckoo’s Egg’
and Microserfs.
I’m a fan of the Basecamp/37 Signals books. Common sense (which is a lot of times opposite of what is currently popular in business circles) and cool illustrations.
Indeed. In addition, I recommend reading literally any of Nicholas Carr’s works.
You took the words right out of my mouth.
Nonfiction: Hackers: Heroes of the Computer Revolution by Steven Levy
A really wonderful history of computing/hacking (in the original sense of the word) culture from its origins at MIT’s Technical Model Railroad Club to the early days of personal computers.
Great question and really cool answers. Here some of my favs:
Business
Zero to One by Peter Thiel (2014), a really good look at the business side of tech. Helps understanding the mind set behind the innovation that came for the Silicon Valley in its golden age.
High Output Management (1983) by Andy Grove, a guide to manage a business by the Intel legend Andy Grove
PC
A personal computer for children of all ages by Alan Kay (1972), great early vision of the laptop and GUI. In some ways we are still not there. http://www.mprove.de/diplom/gui/kay72.html
The mother of all demos Douglas Engelbart (1968), a great early demonstration of the GUI and mouse and, funny enough, cloud computing:). Not a text but it is absolutely legendary https://www.youtube.com/watch?v=yJDv-zdhzMY
Man-Computer-Symbiosis (1960) by J.C.R Licklider, describes the concepts of interacting with a computer. http://memex.org/licklider.pdf
Culture
All watched over by machines of loving grace by Richard Brautigam (1967), highly influential poem https://en.wikipedia.org/wiki/All_Watched_Over_by_Machines_of_Loving_Grace
The Cuckoo’s Egg, OMG how did I forget that one (answer: old age)?
Another one: The Puzzle Palace.
When I read As We May Think the first time, was blown away by the far-sightedness of Bush.
I was just starting out my journey towards a positive relation to technology and it helped me immensely to understand the importance of tech to free humans to do things that have value!