ABSTRACT Drawing on Sen’s conceptual refinements of agency, in particular the distinction between agency freedom and agency achievement, this article highlights the existence of a feedback loop between agency and the capability to aspire. To explore this loop, the author uses John Dewey’s praxeological approach, bringing institutions into the “Capability Approach” along with situated agency. Against this background, she develops an agentive model of the capability to aspire, where the latter is nurtured by the longitudinal and lateral dimensions of experience. While the longitudinal dimension involves temporal processes driven by creative continuity (between past, present and future), the lateral dimension involves relational processes driven by social interactions (between a person and her environment). Institutions are an important part of that environment. By propagating social norms that define roles and behaviours in society, they provide a matrix for individual and collective aspirations, especially for people with fewer individual resources. But as Sen has pointed out, the moral ideals pursued by institutions do not necessarily translate into concrete achievements. This is why Dewey invites us to subject them to an ongoing critical inquiry that confronts their goals to their effective role in people’s lived experience, with the aim to transform them if necessary. The article concludes by discussing the implications of such a transformative inquiry and its potentially empowering effect in voicing aspirations and articulating new ones.