Just such a book is Nassim Taleb's "Antifragile."
I am having to look up a lot of words to read this book. Okay. He often uses these words in nonstandard ways. Oy.
He is against academia in favor of actual practitioners. Okay. He believes that excuses him from justifying most of his (mostly good, accurate) ideas. Oy.
He makes a wide variety of obscure references with little explanation. Okay. He occasionally gives incorrect references (Tantalus had the water and fruit, not the rock.) Oy.
Reading this book without Google would be much, much more frustrating.
As is I'm having to be careful to not spend long on Wikipedia for each reference.
Flaneur. Bricolage. Apophatic. Joseph Tainter. Gladstone. Hormesis. Sarcopenia.
And a number of things I knew but I'll bet most people didn't like Mithridatization.