Courage requires us to persist and persevere despite fear. We make choices everyday—some are courageous, and some are not courageous at all. This dimension of psychoanalytic work is significant, yet relatively neglected in the psychoanalytic literature. Maintaining a courageous stance as an analyst can be challenging and threatening. Often, the therapist faces deeply rooted fears about abandonment, envy, competition, anger, or other forms of intense emotional arousal. This requires us to confront ourselves but also, at times, confront our patient’s behaviors. It is crucial to think and act independently, and deal with their disapproval and opposition, despite the risks challenging patients present. Ultimately, we need to manage our vulnerable feelings while remaining authentic, rather than hiding behind an overly clinical stance. The author presents two patients who required and inspired the courage to face her own anxieties, ultimately contributing to the treatments’ progress.