Mentioned

• One of Glenn's talks on engineering.
• The first part of Hillel Wayne's interviews of people who've "crossed over" to software from "real" engineering. It's really good.
• Herbert Simon, The Sciences of the Artificial, 1969
• Fredrick Brooks, Jr., The Design of Design: Essays from a Computer Scientist, 2010
• David L. Parnas and Paul C. Clements, "A Rational Design Process: How and Why to Fake It", 1986. 
• The Neal Ford talk about constraints was taken down from YouTube because Protecting Intellectual Property by removing a whole talk that uses a short clip is far more important than Mr. Ford's ideas.

Glenn's other recommendations:

• What Engineers Know and How They Know It: Analytical Studies from Aeronautical History, by Walter Vincenti
• Engineering and the Mind’s Eye, by Eugene S. Ferguson
• Definition of the Engineering Method, by Billy Vaughn Koen
• A number of Henry Petroski’s books shed valuable light on the actual practice of engineering:
  • To Engineer Is Human: The Role of Failure in Successful Design
  • Invention by Design: How Engineers Get from Thought to Thing
  • Design Paradigms: Case Histories of Error and Judgment in Engineering
  • Success through Failure: The Paradox of Design
  • To Forgive Design: Understanding Failure
  • Engineers of Dreams: Great Bridge Builders and the Spanning of America (this is quite different from the others, but by telling the real, non-idealized tale of how so many great bridges were built — including several disastrous failures and many other near failures — this book was instrumental in helping me understand how inaccurate the common stereotype of engineering really is)

Credits

Image of double effect distillation chemical plant via Wikimedia Commons. User:Luigi Chiesa, CC BY 3.0. Cropped by Brian Marick.