Using detailed clinical vignettes, the author illustrates that when analysts practice from the inside out, i.e. consider that external obstacles to initiating and deepening an analysis inevitably reflect analysts’ fears of their internal world and of intimacy, they become better able to speak to patients’ long-term suffering. This book, free from psychoanalytic jargon, stands out in its ability to help readers feel more effective, confident, and optimistic about practicing psychoanalysis by providing insights and recommendations about beginning and deepening analysis and sustaining oneself as an analyst over time. It will appeal to both beginners and experienced analysts, as well as supervisors, educators, and those interested in the workings of their minds and in building more intimate relationships.