In this paper, I discuss Geertgen tot Sint Jans' Man of Sorrows (c. 1495) as a tool for perfecting Christian souls. I argue that this image was a meditational aid that was designed to prick the viewer's conscience and engender contrition for his or her sins. In the period, contrition was central to the Christian penitential system and, for the faithful, was necessary for perfecting the soul and reconciling it with God. Geertgen's image required devotees to exercise their memories and imaginations in order to enmesh themselves mentally in the events of the Passion and forge empathic links between themselves, Christ, and his attendants. These links helped the faithful to experience Christ's sufferings in highly individual terms, to understand their own culpability in them, and to awaken sorrow for their shortcomings. The image was a tool that helped fifteenth-century Christians to desire to make amends for their failings by leading them through a process of careful self-examination and self-recrimination. Scourging their innermost selves with contrition, the faithful prepared their souls for the transition out of sin and toward salvation.