Against the scholarly emphasis on precariousness, this article focuses on how gig work in 1970s Singapore was developed with the specific vision of enabling life for the working-class Singaporean family-man. From 1970 to 1993, the taxi company Comfort invested its operations with a powerful vision of the transformative potentials of taxi-driving labor. The gig work of taxis was made to change the work ethic of men, creating workers and fathers who could advance class mobility, nation-building, and the family, raising children who would become ideal workers of the future. Such hopes, however, still relied upon the insecurity of the gig to force the men into adherence. Entangled with patriarchy, nationalism, and familialism, this article examines the compromises exacted through the gig’s capacity to make live, and analyses how Comfort’s experiment has left a legacy in the ways that platformed gig work is governed today, which needs engagement and revision.