How does political advising shape legislative career paths of ambitious actors? Prior research has shown political staff are important gatekeepers and policy actors in their own right. Anecdotal evidence also suggests political advising serves as an increasingly important stepping-stone into a parliamentary career. However, most previous studies of political advising and political candidature only look at legislators who have previous experience as political advisors, thereby selecting on the dependent variable. Using elite survey data from 20 countries and an original longitudinal dataset of political staff in Canada and Australia, this study investigates how political advising impacts the subsequent political careers of advisors in institutionalized democracies. In so doing, this study asks: (1) does political advising experience increase the likelihood a candidate will be elected to political office? (2) If elected, do previous political staffers have different types of parliamentary careers? (3) Are former political staffers more likely to be appointed to the ministry, or to be appointed more quickly?