And/or anything else by Petroski http://en.wikipedia.org/wiki/Henry_Petroski
Systemantics, by John Gall http://en.wikipedia.org/wiki/Systemantics
"27. The Fail-Safe Theorem: When a Fail-Safe system fails, it fails by failing to fail safe."
Someone will inevitably suggest Brooks' Mythical Man Month to a young technologist, so I'll leave that suggestion to that person in this young technologist's career.
Technomanifestos: Visions from the Information Revolutionaries by Adam Brate
Godel, Escher, Bach: An Eternal Golden Braid by Douglas Hofstadter
A Thousand Years of Nonlinear History by Manuel De Landa
Follow for Now: Interviews with Friends and Heroes edited by Roy Christopher
I would also recommend reading the works of Ted Nelson and Buckminster Fuller, as well as some fiction by Neal Stephenson, Robert Anton Wilson and other SF authors.