This book is undertaken by the author who has personally walked the journey of a classroom teacher, middle leader and school principal in the Singapore education system. It is a culmination of two research projects undertaken in two phases - the first is derived from the PhD Thesis entitled The Making of School Principals in Singapore and the second is based on interviews with school principals who have retired from the Singapore education system. Both research projects provide invaluable input to describe the four career phases of school leadership, that is, formation, accession, incumbency, and divestiture. This research describes how the formative years of a school principal have tremendous impact on who the principal is, and how the values and beliefs of an aspiring/potential school leader serve to guide him/her in taking on the principalship post. This well-structured book is both exploratory and descriptive. It provides the necessary background for anyone interested in understanding school leadership as a career. More specifically, it will be of value to educators and stakeholders interested in understanding the nature of school leadership in the Singapore education system.