A high turnover among principals may disrupt the continuity of leadership and negatively affect teachers and, by extension, the students. The aim was to investigate to what extent various work environment factors and signs of exhaustion were associated with reported intentions to change workplace among principals working in compulsory schools. A web-based questionnaire was administered twice, in 2018 and in 2019. Part I of the study involved cross-sectional analyses of the associations 2018 (n = 984) and 2019 (n = 884) between occupational factors, signs of exhaustion, and the intention to change workplace, using Generalized Estimating Equations models. Part II involved 631 principals who participated in both surveys. The patterns of intended and actual changes of workplace across two years were described, together with associated changes of occupational factors and signs of exhaustion. Supportive management was associated with an intention to stay, while demanding role conflicts and the feeling of being squeezed between management and co-workers (buffer-function) were associated with the intention to change workplace. The principals who intended to change their workplace reported more signs of exhaustion. To increase retention among principals, systematic efforts are probably needed at the national, municipal, and local level, in order to improve their working conditions.