Purpose: To fill the gap in theoretical and empirical knowledge on late career in principalship, the aim of this study was to explore the career experiences, needs, and behaviors of principals at this stage. Research method: Life history and semistructured interviews were conducted with 20 late-career principals, 20 schoolteachers, and 10 supervisors. The analysis followed the principles of qualitative research. Findings: The article presents an initial conceptualization of late career in principalship in terms of tasks and issues. Among these tasks are demonstrating professional competence and personal success and obviating continuous decline of physical and energies. Among the major issues are organizational commitment, personal energy, positive attitudes toward changes, a greater sense of professional competence, high self-confidence, and participative leadership style. Implications: Empirical implications for the educational system and the educational research are suggested. Researchers of educational systems are provided with new directions for research on late career in principalship. (Contains 3 tables.)