In this chapter a big picture overview of cultural history provides a context for understanding our present situation in relation to education. After introducing the concept of evolution of consciousness and discussing the research challenges, I take a transdisciplinary approach to evolution, to overcome some of the limitations of Darwinian biological evolution. Three theorists of cultural evolution are chosen—Rudolf Steiner, Jean Gebser and Ken Wilber—with the structural framework being provided by Gebser’s model. An overview of five major transitions of culture and consciousness are presented, the most recent being integral, which is emerging today. The purpose of the chapter is to lay the groundwork for creating conceptual bridges between cultural evolution and education as the book unfolds.