Research indicates that schools do not always provide students with the skills they need for successful transitions to postsecondary education and work. A transition gap is particularly prevalent for "at-risk" students who have difficulty relating learning to future education and career aspirations. A high school counselor, language arts teacher, and technical college assessment coordinator created Plan for Success, an intervention program designed to facilitate more successful transitions for "at-risk" students. Creation and implementation of Plan for Success interventions are discussed as well as resulting improvement in student transition outcomes. (Contains 4 tables.)