The quest for individual freedom was defined and pursued in the twentieth century in an environment shaped by moral norms that were established in the nineteenth century, if not before, but continued to be staunchly defended before undergoing a process of adjustment. At the same time, the question arose of what life would be like once these norms had been shaken off or decisively weakened. Furthermore, the selfhood of those who pushed for liberation was contested between coherence and control, on the one hand, and various modes of transgression, on the other. While such issues were first debated and probed in countercultural circles, they had become a mainstream concern by the end of the century, leading to new uncertainties about how far individual freedom should go and whom it should benefit. This chapter explores how sexuality was restrained by a morality that came to be adjusted in the decades after World War II; how the prospect of a “liberated” life emerged, leading to new expectations, but also creating imbalances and bringing disappointments alongside gains; and how the transgressive urge to expand the ego questioned the norm of coherent selfhood before eventually revealing its darker side.