This collection of seven speculative and critical essays initiates a journey, inviting readers to abide, for a short time, with philosophical themes emerging from aesthetics, poetry, existentialism, and education. It opens vistas into the insightful wisdom of Nietzsche, Heidegger, Jaspers, Rilke, and Plato’s Socrates. The book confronts such perennial issues as the practice of philosophy as a way of life, the understanding of subjecthood and human transcendence, the pursuit of ethical knowledge in ways that inform and direct the choices we make in the company of others, and the philosophical quest for unique ways of learning that transcend contemporary practices embracing standardization and adopting an instrumental approach to education. This book is novel in that it offers these insights across broad, but related, fields of study, for, although essentially a philosophy text, it provides scholarly inroads to the academic fields of literary critique, classical studies, psychology, and educational theory. The text could be effectively employed as a secondary avenue of study in institutions of higher learning, supplementing primary philosophical sources in the curriculum. In addition to programs offering advanced degrees, the book also serves as a challenging introductory text for students at the undergraduate level demonstrating an interest in, and proclivity for, philosophy.