This paper aims to deepen the understanding on how people face experiences of significant ruptures in their life trajectories, in articulation with and in the light of the notion of disquieting experience. Since the semiotic-cultural constructivist perspective in psychology, the empirical corpus that will be taken for analysis, based on this circumstantial nature experience, refers to women’s narratives whose life trajectories were marked by repeated gestational losses. The experience of a gestational loss can be perceived and felt by a woman as an unexpected event, which challenges personal and socio-cultural expectations of what was about to happen – becoming a mother and the birth of a baby. Gaps established between the imagined expectations and perceived reality, produce a non-sense field, experienced by the person as disquieting. In order to reduce the experienced psychological tension and integrate non-sense field in cognitive-affective base pre-existing, new symbolic actions are required to subject in the construction of reorganizers meanings from personal experience – what we denominate semiotic strategies of dynamic self-repair. With this, this paper aimed to shed light on the dynamic and complex aspects of human life related to the psychological processes involved in self repair, due to disruptive events.