This book investigates phenomenology related to essential criterion of study about human longing. It focuses on hermeneutics: interpretation through the lens of philosophy of metacognition. Vital contributions to the book include chapters which explore various facets of the central topic, including the intersectionality of hermeneutics, metacognition, and phenomenology. This collection of critiques and case studies examines the imagined cultural landscape of specific works and associated activities such as fine art, poetry, and digital humanities, which aim to initiate self-monitoring as metacognition, or meta-reflection, by creating interior interpersonal space to overcome adversity. This monograph will be of particular interest to scholars and students of textual hermeneutics and the Humanities, as it relates to prose writing and artistic works in non-verbal media.