I exchanged a few emails with Fred over the years. RIP Fred. Thank you so much for all the wisdom. Sharing one of the last responses here:
Thanks for your kind words. You will find lots of condensed wisdom in the three software books I
value most:
DeMarco & Lister Peopleware
2007. Software engineering: Barry Boehm's lifetime contributions to software development,
management and research. Ed. by Richard Selby.
Hoffman, Daniel M.; Weiss David M. (Eds.): Software Fundamentals – Collected Papers by David L.
Parnas, 2001, Addison-Wesley, ISBN 0-201-70369-6.
You might also like my later book on technical design in general: The Design of Design. Start
with Part II.
I can recommend The Design of Design. It's a bit chatty, but I haven't seen the material in there elsewhere, and it did change my perspective quite a bit, to the point where I could see some "conventional wisdom" at the time being entirely wrong.
The Design of Design was one of the primary inspirations for my open source project Semantic UI.
"[Progressive truthfulness] is perhaps a better way to build models of physical objects...Start with a model that is fully detailed but only resembles what is wanted. Then, one adjusts one attribute after another, bringing the result ever closer to the mental vision of the new creation, or to the real properties of a real-world object
...Starting with exemplars that themselves have consistency of style ensures that such consistency is the designer's to lose."