Drawing on the transformative potential of critical-theoretical learning grounded in the CHAT framework of recognizing the bi-directional relationship between learning and development, the present paper is an investigation of how nine American community college students participating in a critical learning community (Peer Activist Learning Community) make sense of and position themselves towards the pursuit of higher education. The paper has two key findings: (1) students primarily draw on vocational discourse paired with a conceptualization of learning as rote learning (i.e. memorization (...) and acquisition of skills) in making sense of their pursuit of higher education, and (2) students embody a transitional positioning toward the community college, which poses the ontological challenge of belonging to an academic institution while seeking to negate this belonging. The findings are framed and discussed in particular through the lens of the transformative activist stance (Stetsenko) with an emphasis on the recognition of education as the process of becoming human as well as with a focus on the transformative potential of meaningful learning experiences. I conclude by suggesting the need for transforming the aim of retention studies as well as put forward the suggestion of re-conceptualization the concept of belongingness in educational psychology in light of the CHAT framework. (shrink)