The voluminous diaries of Khalil al-Sakakini (1878-1953), written mostly in Jerusalem between 1907 and 1952, have been a rich source for historical inquiry, yet there has thus far been little attempt to provide a thorough investigation of this complex personage. The period during which Sakakini lived and wrote was one of undeniable change, yet the ways in which he has been described in the secondary literature on this period (devoted nationalist, patriotic father, dedicated teacher, etc.) have left us with little room to examine the way he made sense of these changes. Throughout the diary, we observe Sakakini constantly negotiating, defining and redefining his different selves, often leading to contradiction. His curious and mercurial disposition can therefore provide a lens through which we may examine the ways in which these changes and ideological confrontations played out in the mind of an individual. The aim of this study is to respond to the existing literature by providing an in-depth examination of this historical character as he presents himself in his diary. Using theories from psychology and sociology (cognitive dissonance and habitus), this research adds to our appreciation for the way in which social change brought about by conflicting nationalist and colonial ideologies can impact an individual. As a work in micro-history, this investigation thus has broader implications for an evaluation of historians' tendency to construct dominant narratives on this period in Palestinian history.