Today there is often a preference for collaborative and collective activities, perhaps with a goal of training individuals to become a new kind of socialist self. Many are encouraged to become almost constant performers for others on social media, to be thoroughly shaped by the available reinforcement. At such a time it might be instructive to examine several thinkers who strongly valued solitude and a fervent resistance to being a performer for others, seeing these as necessary conditions for shaping an individual life that might be found worthwhile. This book examines in this regard Franz Kafka, Marcel Proust, Fernando Pessoa, Ludwig Wittgenstein, Friedrich Nietzsche, Henry James, T. S. Eliot, and Klaus Mann. While their personal lives are probably not enviable to most observers, they face up with a special intensity and honesty to the human experience of aloneness, loss, separateness, depression, and metaphysical emptiness, as well as the peculiar pressures of individuation, self-consciousness, and agency. At a time when students are encouraged to read literature in order to draw correct moral and ideological conclusions, it might be beneficial to encounter thinkers and writers who can help them face up to their own experiences of loneliness and of the pressures of being an individual self, once humans with their hunter-gatherer brains have moved into sophisticated modern societies.