This article examines the relationship between skill acquisition and the constitution of economic selfhood in Trinidad. Drawing on ethnographic fieldwork among garment workers in a context of industrial decline, I show how their formal, informal, and illicit means of acquiring sewing skills are inextricably linked to the fragmented and unstable economic opportunities available to them. Learning to sew means learning to be a flexible economic actor, which helps workers survive but disadvantages them in waged labor relationships. By investigating the role of pleasure in self-training, I emphasize the neglected importance of emotion for understanding livelihood strategies. (Contains 2 notes.)