The book reflects on a journey of the author, transitioning from Rural to Urbanised settings in search of quality education in SA. It begins by exploring rurality- rural life integrated with the colonial past that has left the country with a task of an ongoing struggle for decolonization in the education system. The book argues for a rethinking of what University readiness means, and the implications of this for student retention and exposing real socio-economic and psychological life challenges experienced by students in their quest for becoming the next point of reference for others.