This essay excavates early modern concepts of contentment in order to reconsider the political significance of Shakespeare’s As You Like It. Drawing upon the etymological connection between “content” and “contain,” Renaissance writers discussed contentment as a means of fortifying the self: of protecting the subject from the external threats of capricious fortune and the internal divisions caused by the passions. For his part, Shakespeare explores the relationship between individual, interpersonal, and political contentment. In As You Like It, contentment both sustains the individual self and unites the self and other peaceably and profitably. Upon this foundation of shared positive affect, Duke Senior builds an Arden society that opposes the political oppression of the court and promotes political virtues of liberty, counsel, and consent. Shakespeare juxtaposes this representation with the powerful desires of Rosalind and the isolating discontent of Jaques, but he nevertheless maintains the political value of contentedness. Resisting reductive twentieth-century understandings of contentment as resigned, static, and socially conservative, I argue that Shakespeare engages the prominent period discourse on contentment to rethink the prevailing political order.