Thomas Winn is a philosopher and doctoral student with an interest in the phenomenon of nihilism and the post-modern human condition. In his work, he draws on the historical tradition of thinkers which include Hegel, Nietzsche and Heidegger, as well as contemporary philosophical work of Gianni Vattimo and Slavoj Žižek. In this discussion we seek to explore topic of nihilism and its overcoming with Nietzsche’s concepts of the will to power and eternal recurrence. Here we situate both concepts in relation to the postmodern problem of “the understanding’s” desire for “fixed values”, and its relation to the thing-in-itself, which appears to be fundamentally transient, and thus unfixable. We discuss how this situation produces a source of resentment and general negative emotionality, which is involved in confronting a groundless real (e.g. Death of God), or a gap between the “I” of the understanding and the “it” of the fixed representation. To really reconcile ourselves with this groundless real, we suggest that both the will to power and the eternal recurrence point towards a becoming of becoming itself. Practically speaking, when the understanding no longer fixes even the notion of becoming, letting it go for an affirmation of life flux, we may be free to explore the absolute or the eternal, as that which is a continually recurring novelty in the gap.