Abstract This article examines four different trajectories of contestation individuals go through. We highlight how the five motivational dynamics function per trajectory, depending on how they interact within individuals’ psyche, their perceptions, and the surrounding political setting. We argue that through the citizens’ narratives about these political moments we can better understand how the motivational dynamics function per trajectory of contention. Our focal point is to disentangle how, under the same political conditions, individuals act differently, even though they might hold the same political stances. Repression is a focal point of analysis in the article showing how the individuals within the various trajectories react to regime’s repression differently. It is the context within which individuals within the four trajectories function that is affecting their behaviour. We investigate how the ways individual express dissent change by interacting with the regime whose repressive actions might push them to change their attitudes.