This paper will report on one principal’s account of his first two years as a leader of a secondary school in a socio economically deprived community in England. The school had a history of failure in terms of independent inspections of its pupil results and a turbulent history in terms of leadership. Whilst there is an increasing literature which focuses on the the roles of novice principals and principals in “turnaround schools”, there is little which investigates how experienced principals’ values and identities are tested as they create and build success. The paper will draw upon the principal’s own autobiographical account and a series of face to face interviews which focused on perceived challenges and changes in his values and sense of identity during the first two years at the school as he exercised his leadership in various “sites of struggle” in a context of high intensity support from the school sponsors (a university/ business partnership), extreme, time limited accountability demands by government and a staffing configuration which was dominated by a majority of experienced staff who were present before his arrival, a minority of senior staff together with large numbers of relatively inexperienced staff who were appointed by him.