Ask HN: Good books on philosophy of engineering?

I can't understate just how great "Waking Up: Overcoming the Obstacles to Human Potential" by Charles Tart (2001) is. It's a cross between engineering and the spirituality (although I argue, it's more on the philosophy and psychoanalysis of engineering than spiritual).

I wrote a (short) review on the book directly after reading it here[1]. I've since reread the book, and while some of my opinions on it are the same, some I understand the nuance much more in context of the rest of the book, I need to update it.

1. https://macleodsawyer.com/books/waking-up/

And if you want something a bit more relaxed and updated, The Dude De Ching[1], is quite good. It's a rewrite based around the core concepts of Dudeism, a fan-made spiritual practice based on the character "The Dude" from The Big Lebowski.

> The rug is a fabrication which ties our ruminations together.

1. https://dudeism.com/thedudedeching/

Edit: There is an online version available as well, https://aui.me/text/the-dude-de-ching/

I read it last year and it is fantastic - super absolutely ultra highly recommend that everybody read it. Run, don't walk, towards this book!

Anything written by Langdon Winner https://en.wikipedia.org/wiki/Langdon_Winner

I would begin with "Do Artifacts Have Politics?" and continue with "Autonomous Technology: Technics-out-of-Control as a Theme in Political Thought", M.I.T. Press, 1977.

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."

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