The paper aims at providing insight into ways of the early identity formation of a school principal in an upper secondary school within a Norwegian social, cultural and political context. The underpinning methodology is a theoretical perspective which focuses on the identity projects of school leaders. This is achieved by employment of the life history method (Goodson & Sikes 2001). The analysis builds on a study in which the interplay of agency and structure through the use of the life histories of school principals across four countries has been explored (Sugrue 2005). Open-ended interviews have been conducted where the school principal tells about her work, background, experiences, and career. In addition, the analysis draws upon data from audio-recorded meetings where the principal reflects on leading an ongoing school improvement project with her leadership team.The discussion deals with the principal’s way of framing and telling about her career paths, coping-strategies, work commitment, how she positions herself and her perception of power. What emerges from the analysis is a more complex understanding of how policy and school contexts interact with the individual lay theories of the principal and the history of schooling that creates various kinds of trade-off.