The process of educational and vocational development does not occur at a single point in time. Many indicators of dropping out of high school, for example, are present by middle school (Alexander et al., 1997; Balfanz et al., 2007). Yet, research and practice focus almost exclusively on enriching the learning and work experiences of high school students (cf. Fouad, 1997; Solberg, Howard, Blustein, & Close, 2002), and little is known about the factors related to career progress in urban middle school students. In order to address this gap, the current study used a developmental contextualism framework to explore the relationship of a variety of academic and motivational factors with students' career progress at the middle school level. Specifically, this study investigated the contributions of school engagement, academic motivational beliefs (self-efficacy, intrinsic value, skepticism), gender, school grade, prior attendance, and prior Massachusetts Comprehensive Assessment System (MCAS) scores (Math and English Language Arts, (ELA) to career progress. Urban middle school students in 6th, 7th, and 8th grade completed self-report questionnaires assessing career progress, school engagement, and academic motivational beliefs. Academic achievement (i.e. MCAS Math and ELA scores) and attendance for the previous academic year were obtained from school records. Results of the study reveal that (1) Prior academic achievement (MCAS Math and ELA scores), attendance, gender, and grade only account for a small proportion of variance in career progress; (2) Middle school students who have progressed further in career development also demonstrate higher school engagement and academic motivational beliefs; (3) Career progress explains school engagement beyond the effect of prior school achievement; and (4) Academic motivational beliefs mediate the relationship between career progress and school engagement. The findings suggest that middle school students sustain career progress despite levels of past academic achievement. They also support prior research that links career progress with school engagement among high school students (Kenny, et al., 2007), and suggests that motivational beliefs may be a link in explaining that relationship.