There is concern among information systems (IS) scholars that the lack of philosophical engagement and conviction among the research community threatens the future integrity and creativity of the research process. The paper seeks to respond to Weber’s call for IS researchers to clearly present their “ontological and epistemological assumptions” and to accept Myers’ invitation for “further reflection and debate on the important subject of grounding interpretive research methodology”. The approach of the paper is to present a self-reflective case study, following Schön, of the author’s doctoral research journey. The paper aims to make a contribution by: presenting the work of two philosophers new to the IS discipline and proposing a dynamic model that opens IS research to engagement with the complex philosophical universe. The argument is developed using analogy and by describing the author’s journey towards a philosophical system that reflects his worldview.