The purpose of this qualitative, explanatory, single, case study was to explain how new and experienced principals in one 9-12 school district located in California perceived their transition to the principalship. Data were collected with regard to perceptions of administrator preparation and induction programs, along with their perceptions of enablers and barriers to retention. This study took place in the state's largest 9-12 school district. William Bridges' transition theory served as the theoretical framework. Research questions focused on how new and experienced principals perceived transition to the principalship, their administrative preparation program and district induction programs, along with six new principals participated in semistructured interviews and four experienced principals participated in a focus group. The researcher compiled notes during interviews and focus group. Initially, a deductive coding process was followed by inductive thematic analysis. Five themes resulted: Career Transition, Preparation/Induction Programs, Enablers to Professional success, Deterrents to Professional Success and Advice to Self. This study provides data on the needs of new principals and how to improve preparation programs and district induction programs to expand enablers to success and to reduce deterrents to professional success. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]