This work explores the relationships between principals’ motivations for entering the principalship and the difficulties they experienced during their first year as principals. Survey data were collected from a sample of 2042 Spanish principals. They answered a questionnaire assessing intrinsic and extrinsic motivations, difficulties experienced when doing instructional, informational, and administrative tasks, and other personal and contextual characteristics. The scales developed to measure motivations and difficulties displayed adequate psychometric properties. The results showed the preponderance of intrinsic motivations. Administrative mundane tasks were perceived as the most difficult ones. We also found that non-administrative instructional tasks were more difficult for those principals who were more extrinsically motivated. Some gender differences were observed in motivations and difficulties. Women placed lower value on extrinsic motivations than men. Furthermore, while the difficulty of administrative tasks in their first year as principal was placed higher by women than men, those tasks that are more relationship-oriented (i.e. informative and instructional tasks) were rated as more difficult by men than women. Although internal incentives and administrative overload characterize most of the public Spanish principals, some findings pointed to the possibility of other profiles of principals that should be investigated in further studies. Implications for the design of principalship training are also discussed.