The 'free will' debate has been an issue of serious and significant tension in the history of ‘Western’ philosophy. For Martin Heidegger and Jean-Paul Sartre, debate has been rendered intractable by a fundamental misunderstanding of the terms involved. This is exacerbated, they argue, by a failure to identify and adopt an appropriate methodological approach to the problem. In this respect and for both philosophers, this error in the free will debate is symptomatic of a broader misunderstanding of philosophical enquiry as such and the method it necessitates. For Heidegger, the entire history of ‘Analytic/Western’ ontology has been fatally misconceived as a result of an effort to define the being of entities in static terms. The insistence on framing questions in respect of whether/what a being ‘is’ thus obstructs any meaningful enquiry by conceding existence at the outset of the investigation. He demands nothing less than the ‘destruction’ of that framework as a necessary step towards a radical account of freedom as a necessary feature of human experience. Sartre’s project is founded on Heidegger’s argument though he is critical of what he considers the ethical ambiguities inherent to Heidegger’s account of Dasein. Instead, Sartre pushes the premises of Heidegger’s project into a definitive claim about the nature of consciousness. Therein he argues that as the only being for whom ‘meaning’ is possible, consciousness is distanced from beings by ‘nothingness’ which ensures its ontological freedom. We propose that a thorough investigation of their projects will reveal an account of ontological freedom that does not suffer from the shortcomings of Sartrean existentialism whilst avoiding the methodological missteps of the traditional discourse. Moreover, we will suggest that overcoming Heidegger’s ambiguities can be achieved by advancing his concerns into an interrogation of the ground of Dasein and its ontological priority. Thus we can satisfy Sartre’s criticism while reinforcing the commitment to a radically different approach to philosophical enquiry. Our investigation will argue that although Sartre has misconstrued Heidegger’s work, making comprehension of his freedom all the more complicated, an argument persists which sheds new light on a seemingly stubborn philosophical problem. In so doing, a challenge will be presented to some of the fundamental premises of modern philosophical discourse, promising to reorient the approach to enquiry as such.