Inspired by Amartya Sen's conceptualization of capability, this article examined how the introduction of an experience-driven (ED) framework into the capability approach helps inform the delivery of a career support service project targeted at youth aged 15-21, who are not in education, employment or training (NEET youth) with difficulties to develop their career capabilities. Based on a thematic analysis of ten individual interview transcripts collected from five career practitioners and five ex-users, the study discussed four interlocking domains of experiences and experience-driven career interventions for enhancing youth's capabilities to aspire and realize aspirations with a transition from the zone of proximal development to the zone of aspired development, namely, recognition, exposures, self-growth and transferability. We recommended further research studies on evaluating the effectiveness of using the ED framework for applying the capability approach to strengthening the career capabilities of service users characterized by diversity and vulnerability in different service settings.