Rites of passage hold meanings and serve purposes in traditional cultures that can inform us in dealing with challenges of adolescence. This work unriddles the transformative nature and the mystery of the Kikuyu circumcision ritual irua ria anake. Key questions are addressed pertaining to: i) the meaning of the circumcision ritual practice to the contemporary Kikuyu males, ii) how the circumcision ritual plays a transitional role and how it influences self-redefinition, and iii) what the core philosophy behind the circumcision ritual practice is.