In this study the authors highlight the conceived roles of occupational therapists by contrasting them with the conceived roles of teachers in assisting students at risk of academic failure in a continuation high school transition to postsecondary education. From analyzing transcripts of one-on-one semi-structured interviews with five teachers of a continuation high school and with seven occupational therapy staff in a life-skills training program, three themes emerged with relevance to the youths’ transition, which differentiated the teachers from the occupational therapy staff. Both cohorts recognized college as the preferred path to adult roles, but differed in regard to their view of the achievability of the goal for the at-risk youth served. Both cohorts identified the youths’ personal behaviors as impediments to these youth meeting their goals. Teachers emphasized academics and occupational therapy staff emphasized life skills when assisting the young people. Occupational therapy staff's interventions underscore hope and support of students’ long-term goals with the aim of engaging these young people in short-term planned-action, which may be beneficial to this population and warrants further study.