Young men in precarious situations of persistent un(der)employment in post-civil war Freetown, Sierra Leone are depicted in popular and policy debate as “stuck” economically or “dangerous” and prone to violence. In the present paper, by contrast, we draw on young men’s explanations of their work and livelihood struggles as “straining.” We explore the logic of straining, its innovations and demands, and its geography across the city, especially where acts of straining interface with the prohibition and criminalisation of informal trading. We argue that straining innovates and endures because of (not despite) young men’s marginalisation and limited autonomy and power. In this context, young men build forms of provisional agency and enact dynamic forms of waithood, in their strategies to earn a living to try to support their families and to negotiate a transition from youth to manhood. Drawing on this research, we argue for a more complex understanding of young men at work in Freetown, in particular, and of the “youth bulge,” in general, in African cities.