Our general understanding of social class in the workplace has tended to focus on either the negative effects of one’s lower social class background or the beneficial effects of one’s higher current social class. Although unique challenges exist for individuals in the pursuit of upward mobility from childhood to adulthood, we suggest overcoming these hardships and barriers provide unique emotions and attitudes that will not be present in those lacking these contrasting experiences. Taking a transitional perspective and drawing on social comparison theory as well as research on temporal comparisons, we theorize individuals achieving upward mobility in social class (vs. stable upper-class) feel more pride and ultimately experience more positive appraisals of their jobs as a result. We support our predictions across three archival studies (a longitudinal survey of participants from Wisconsin and two nationally representative surveys of U.S. adults), which revealed current social class is positively related to, social class background is negatively related to, and—in conjunction—upward social class mobility is positively related to pride and ultimately job satisfaction. While scholars have long emphasized the disadvantages of having lower childhood social class, we point to an affective and attitudinal silver lining that exists in overcoming these social class hurdles.