My dissertation attempts to understand the value of sociality and solitude in a good life. I explore this question in the writings of the Basque poet, novelist and philosopher Miguel de Unamuno and the foremost American transcendentalist, Ralph Waldo Emerson. One chapter is devoted to each author's views on solitude; another, to each author's reflections on society. Both authors support the view that the value of society and that of solitude depend on one another. In the first chapter, I distill Emerson's distinctive understanding of solitude as a relation involving newness, intuition and inwardness. Solitude allows us to tap into a transpersonal mind as both the creator and a universal wellspring of inspiration. The environing natural world supports this process, attuning the mind to the inspiration that emanates from the aboriginal self. The results of this process eventually come to light; they are communicated to and embraced by other persons. The second chapter inscribes the relationship between the civilization and the solitary individual in Unamuno's agonistic epistemology, which posits both an irresolvable tension and interdependence between reason and faith, and between the universal and the singular. Unamuno advocates living by a personal, incommunicable truth. I show that his retelling of the tale of Don Quijote illuminates and motivates this ideal. Chapter 3 traces the themes of love and friendship through Emerson's work. My starting point is Emerson's reflection on his bereavement at the death of his son Waldo. To make sense of those reflections, I examine other writings that suggest that sociality is a necessary condition of existence and perception. Such a view is contrasted with one Emerson calls the impersonal , which accords persons ephemeral, symbolic value. I try to show how Emerson's clashing views can be harmonized. In chapter 4, I examine Unamuno's two accounts of the role society plays in the quest for immortality. Like Emerson, Unamuno ties sociality to existence. In The Tragic Sense of Life, he argues that suffering leads to all-embracing compassion which discloses a transpersonal consciousness, the Living God, who can guarantee our immortality. In How to Make a Novel, Unamuno suggests we can aspire to endless life through the conversation of literature, which joins individuals of different ages. I conclude the chapter by showing how Unamuno's literary theory illuminates the relationship between Don Quijote and Sancho and, by extension, human relations in general.