Jtsummers

The contents of TAOCP are very well edited, just massive in scope

I still thought it was a worthwhile read and will probably include it in a list of books I'd recommend to a mentee in the future.

A Philosophy of Software Design by John Ousterhout

I'd still recommend it to junior colleagues paired with some caveats about avoiding seeing the world in black & white.

I also recommend The Goal.

I'd rather read it once more before actually recommending it.

I’ve tried reading other books, like Jorge Luis Borges’ Ficciones, but I’ve found it to be above my present level.

Eric Evans' Domain-Driven Design.

nothing new in the world, literally everything I had tried to improve was also a problem 30-50 years earlier

The Psychology of Computer Programming by Gerald Weinberg. There's a silver anniversary edition, that's the one to get. It has the author's commentary framing each chapter where he reflects on the contents.

The Psychology of Computer Programming by Gerald Weinberg.

Concrete Mathematics is a completed text that expands on, in particular, the math in Chapter 1 of TAOCP.

Sterman's "Business Dynamics" may be of interest to you, but it's pricey.

check out his Computers & Typesetting