In this chapter, I explore how the conflict between freedom and control presents and has been viewed throughout Western Civilization. Philosophical and psychological conceptualizations of autonomy and heteronomy are explored to give a better understanding of how Western psychologists and philosophers such as Freud, Horney, DeBeauvoir, and Sartre have approached the conflict. By tracing the history of these theories, foundations for modern understanding of autonomy are given context. This context is then used to look at how psychology has tried to make sense of the conflict between autonomous action and societally imposed restrictions and controls, both at the level of the individual and the level of psychological practice itself. Theories of personality and individual difference are discussed to provide insight into how the need for autonomy varies from person to person as well as to show how particular traits and factors contribute to these individual differences. The chapter concludes with a look at and critique of one of the more prominent theories in psychology regarding autonomy, Self-Determination Theory, to reflect on how there is still work to be done with resolving the conflict both at the individual and societal levels.