In this presentation, I examine how grief, when evoked as a proactive practice through envisioning hypothetical losses (such as the death of another subject, the termination of a relationship, or the irrecoverable deterioration of one’s living environment, etc.), calibrates ethical discernment and conduces moral progress. Proactive grief confronts an individual with the contingency and vulnerability inherent in actions, subjects, and relationships. In so doing, it reveals moral significances that are intertemporal (discovered only retrospectively yet projected forward), modalized (predicated on potential rather than actuality), and interpersonal (dependent on the perspectives of subjects) — features that distinguish moral considerations. Proactive grief hence grants epistemic insight into moral reasons in situations where prudential concerns might eclipse them, and provides motivational access towards moral ideals, which are often obscured by personal biases and egoistic concerns when one's viewpoint is limited to the present, the actual, and the personal.