The so-called Bolivarian process seems to be coming to an end, and Latin American Left is trapped in a meaningful dilemma: whether to continue with neo-enlightened processes belonging to the 1990s or consolidate itself in the particular ethos of the Chavista model. With that in mind, the article provides a close philosophical observation focused on the Kairos that shook the continent by the late twentieth and early twenty-first centuries, as well as on other peculiar elements of the process. This will be able to clarify this critical situation and lead to possible orientations in the future, within a context of permanent unpredictability and recurrence.