Based on an essay he wrote for Poets & Writers magazine, Jesse Browner, a novelist who finds himself torn between his creative calling and a full-time job in the civil service, asks hard questions about the choices life imposes on us, and our tendency to believe in a parallel, alternative existence where we might have felt more fulfilled, more free, more true to ourselves. He wonders: Is the genuine artist made by single-minded devotion to his craft? Do we compromise our dreams in service to family and work? In the face of life's inevitable disappointments, how do we learn to reassess our own achievements and live without regret?

These questions prompted Browner to take a hard look at the lifelong journey that brought him to this moment of existential doubt. He divides his adult life into five distinct phases: ambition, love, work, fulfillment, and wisdom. Sketching portraits of himself at each stage, he looks for the idiosyncrasies, blind spots, and commonalities that led him to question every assumption he has ever made about who he is and the nature of his ambitions, his successes, and his failures. He also draws on the lives of others, from Franz Kafka to indie rocker Elliott Smith to his own sister, in search of understanding and guidance. What he finds in his courageous quest is inspiring and honest—sometimes brutally so—touching on what it means to live a life with intention and meaning.