This study analyzed how a cohort of eight young women who underwent certain difficulties whilst at secondary school experienced their transition from secondary school to either work or further education. It explores changes in their perception of events and happenings that they classified as significant to them, and the influence that these changes of perception had on their evolving life-course. While not formally classified as emotionally or behaviorally challenged, all the participants in this study claimed to have had varying depths of difficulty when at secondary school, some alleging that they had been classified as troublesome by their teachers and others claiming to have seen themselves as disruptive in classroom settings. The study was informed by the participants' voices about how they saw their transitions being forged and has a phenomenological focus.