This paper presents a qualitative study about how teachers entering the profession at different times over the last five decades made sense of their professional lives and continuing professional development (CPD) experiences against the backdrop of the CPD policy infrastructure and wider educational context in Hong Kong. The life history method was used. The findings of the study show that teachers' self-directed professional development was driven by a commitment to the moral purposes of teaching, characterized by their active agency in professional knowledge construction, and supported by facilitating organizational conditions in schools. The study also reveals that fierce competition among individuals and schools, intensification of work, stress, uncertainty and alienation on the part of teachers evidenced the de-humanizing effects of an increasingly managerialist and market-oriented approach to school education. Implications for educational leaders at policy and school levels and teachers will be discussed. (Contains 2 tables.)