Don't overlook books that are critical of engineering as it is often practiced and how it fits into our society:
Computer Power and Human Reason by Joseph Weizenbaum (1976). Weizenbaum wrote
Eliza, the first AI chatbot, almost sixty years ago and was appalled at the reception. This book is still very pertinent, especially the Introduction,
Chapter 1 On Tools, chapter 9, Incomprehensible Programs, and chapter 10,
Against the Imperialism of Instrumental Reason. Chapter 4, Science and the Compulsive Programmer, is one of the first written accounts of the hacker culture.
Weizenbaum's original paper on Eliza (1966) [0] is still very pertinent to the present generation of chatbots, especially the introduction and discussion.
Tools for Conviviality, Ivan Illich (1973) [1]. Influenced recent work
by the computer scientists Steven Kell [2],[3] and Kartik Agaram [4].
Computation and Human Experience, Phil Agre (1997) (excerpt at [5]). Agre
got a PhD in AI at MIT in the 80s and 90s and became very critical of the field.
I think his shorter writings [6][7] are a better introduction, especially the personal memoir at [6]:
"about how I became (relatively speaking, and in a small way) a better person through philosophy."
A critical book I enjoyed when I read it (before starting my career) was The Real World of Technology: https://www.goodreads.com/en/book/show/1291973. Worth it just for the first chapter where she defines technology as practice, which helps clarify why the classic “technology X is a neutral tool that can be used for good or ill” argument isn’t very satisfying.
That said, I haven’t read it in a long time so not sure how well it holds up.
I need to read Illich. I've been following The Convivial Society, a newsletter whose author is very influenced by Illich.
My introduction to tech criticism was To Save Everything, Click Here by Evgeny Morozov. He describes a lot of tech culture as "solutionism" which I think is a great lens to have in your pocket.
I’ll second this. A philosophy for engineering is nestled I think in the larger “philosophy of technology”, but this field of philosophy has traditionally been a lot more critical of technology than most of us can stomach today. This is a really good map of the field that not many know about, written in 1995:
Computer Power and Human Reason by Joseph Weizenbaum (1976). Weizenbaum wrote Eliza, the first AI chatbot, almost sixty years ago and was appalled at the reception. This book is still very pertinent, especially the Introduction, Chapter 1 On Tools, chapter 9, Incomprehensible Programs, and chapter 10, Against the Imperialism of Instrumental Reason. Chapter 4, Science and the Compulsive Programmer, is one of the first written accounts of the hacker culture.
Weizenbaum's original paper on Eliza (1966) [0] is still very pertinent to the present generation of chatbots, especially the introduction and discussion.
Tools for Conviviality, Ivan Illich (1973) [1]. Influenced recent work by the computer scientists Steven Kell [2],[3] and Kartik Agaram [4].
Computation and Human Experience, Phil Agre (1997) (excerpt at [5]). Agre got a PhD in AI at MIT in the 80s and 90s and became very critical of the field. I think his shorter writings [6][7] are a better introduction, especially the personal memoir at [6]: "about how I became (relatively speaking, and in a small way) a better person through philosophy."
0. https://dl.acm.org/doi/10.1145/365153.365168
1. http://akkartik.name/illich.pdf
2. https://www.humprog.org/~stephen//research/talks/kell19de-es...
3. https://www.humprog.org/~stephen//research/talks/kell19softw...
4. http://akkartik.name/akkartik-convivial-20200607.pdf
5. https://pages.gseis.ucla.edu/faculty/agre/che-intro.html
6. https://pages.gseis.ucla.edu/faculty/agre/notes/00-7-12.html
7. https://pages.gseis.ucla.edu/faculty/agre/critical.html