In this text, I use an analysis of ambiguities in Heidegger's discussions of ontological death in Being and Time as a point of departure for an interpretation of transformative and nondual aspects of Heidegger's philosophy. I begin by arguing on the basis of careful intratextual and intertextual considerations that Being and Time is unresolvably ambiguous regarding the relation of ontological death to literal death. Rather than rejecting Heidegger's text on the basis of this ambiguity, I look to Heidegger's biographical and intellectual contexts for clues regarding the role of death in his thinking. I show Heidegger's proximity to intellectual and spiritual narratives---including texts from Christianity, Western philosophy, Buddhism, and Taoism---in which death is a metaphor and/or a catalyst for radical personal transformation. I show how Heidegger is aligned with such transformative traditions and how contemporary academic readers may bring to Heidegger's texts philosophical aims and methods which are unwittingly misaligned with Heidegger's own aims and methods. In order to illuminate such potential methodological gaps, I examine diversity in conceptions of and approaches to philosophy and develop provisional notions of trans-theoretical philosophy, extra-theoretical philosophical goods, transformative philosophy, interstructural transformation, and interstructural dysgnosia. I then show that Heidegger saw a particular kind of transformation as paramount in his own philosophy---a transformation which goes beyond the theoretical and representational thinking which characterizes most contemporary philosophy. Finally, I develop a nondual reading of several transformative themes in Heidegger's philosophy and argue that ambiguity is unavoidable given some of Heidegger's transformative philosophical aims and methods. I conclude that Heidegger uses ambiguity to help inquirers to transcend representational thinking and to access the non-theoretical clarity of ontological self-transparency which arises in a transformative, nondual recognition of the clearing of being.