One of the obstacles to democratic development is the reluctance of political leaders to leave office. This article argues that alongside democratic constraints and accountability, leaders’ career concern—specifically, the possibility of post-tenure careers—is an important factor behind their rotation in office. While literature exists about leaders’ exit and fate, we lack a systematic understanding of their careers and whether former rulers retire, remain in politics, or pursue civil service, business, international, or non-profit careers after leaving office. Drawing on the new data on the prior- and post-tenure occupations of leaders from 1960 to 2010, the article explains how democracy, personal background, and the economy influence what ex-leaders can do, and why. In turn, over time the post-tenure careers of prior rulers may strengthen the precedent behind the institutional routinization of the rotation in office norm—an important component of democratic consolidation.