I recently read a book by the David Foster Wallace called Everything and More: A Compact History of Infinity. I'll try to think of some more examples, but this was the first one that came to mind. I really like it because it is a bit more modern than other academic philosophical texts on this tough topic. He was also a novelist and top notch interviewer, so it's a very enjoyable and relate-able read.
He discusses a bit of his own first-person experience dealing with abstract concepts, and also tackles the topic from an historical context. He discusses the scientific, philosophical, mathematical, psychological, and even physiological implications of pursuing the abstract quite a bit in this book which, ultimately, discusses mankind's invention of the concept of infinity. Bonus: thought exercises!