This introduction presents an overview of the key concepts discussed in the subsequent chapters of this book. The book presents an overview of the evolution of the genus Homo across the Pleistocene. It seeks to connect the dots in the processes of 'becoming wise' from an evolutionary anthropological approach to the emergence of meaning making in the archaeological record across the Pleistocene. The book provides an overview of the archaeological evidence for particular patterns of social learning and complex sociality in the Middle Stone Age of South Africa that may set the stage for the consideration of patterns and processes related to intimations of humility. It demonstrates how, in Peirce's logic, diagrammatic reasoning gives rise to the possibility of sign-based thought experiments and related mental manipulations, while hypostatic abstraction is the process of turning a thought into a thing. The book suggests that diagrammatic reasoning and hypostatic abstraction operate in a complementary way, and are jointly the basis of self-transcendence.