Through discursive essays and poetic narrative, Antithetical Commentaries on X, Y and the Disruption of Being explores the tenuous relationship between modes of measurement and the struggle for human relevance in the post-contemporary digital age. In the introductory essay, “Not the Feather, but the Bird”, I give an overview of the inherent problems of object-oriented ontology, and how it relates to aesthetics and social issues of our times. In the Developmental Overview, I detail how I developed my installation approach and techniques, particularly with regard to the three-way dynamic of the artist:work:viewer relationship and how it can encourage a ‘transgression’ that leads to the possibility of a transformative awareness of being. Subsequently, I present a series of ‘antithetical’ commentaries that neither explain nor expand the installation, rather, they create a non-binary duality that, through an entirely non-linear anti-narrative, work to erode the overlay of personal, civic and collective grids present in the memory space/time referenced in the video, TAG. Finally, in “Grid: Towards a Transgressive Humanism.” I propose a path by which installation art might serve to create transgressive opportunities for viewers, rather than the transcendence sought through religious rituals, which often reinforce stigmas, fears and authoritarian social dynamics, or worse, the reductive loop, of many contemporary approaches to art which proclaim their detachment in wordy displays, essentially leading to a form of aesthetic nihilism. This Transgressive Humanism is not presented as a dogma, but rather a revitalization of the work as a vessel of possibilities, an agent of creative growth for the artist and the viewer.