The high dropout rate among working students in higher education in Portugal, including both those who are older and at a mature stage in their professional careers and those who are young and recent workers, is one of the main concerns of educational policy. Identifying the drivers of the academic pathway for these students is essential to promote successful education and increase labour productivity and business competitiveness. Using an extensive longitudinal database of personal, course, and employment variables of 1,561 working students from a Portuguese higher education institution, we perform a duration analysis to determine and compare the factors that drive the dropout and graduation risks of mature and young working students in higher education. The results show that, in general, young working students are more positively influenced by financial aid, their motivation for the course, and the desire to find a new qualified professional career, while mature working students depend more on social and academic integration. The accumulation of knowledge/skills in the 'out of class' experience seems to contribute positively to academic performance.