Could students who practice self assessment turn their focus from grades to learning? An international review of the literature suggests that grading remains a dominant motivator and that self assessment is apparently rare. This challenge exists despite growing evidence that self-awareness is a critical life skill. In this study, instructors and students used David Carless’s (University of Hong Kong) Learning-Oriented Assessment Project survey to focus on learning and stimulate discussion. Survey and discussion data was captured and aggregated around the motivations and barriers for designing and experiencing self assessment. Results indicated that students and instructors felt unqualified to give self assessment feedback or justify grades. In spite of these barriers, those who persisted to try self assessment were motivated by the way student outcomes achieved greater alignment with evaluation criteria, and published and unpublished course objectives. This study was conducted in a higher education setting, but educators from all settings will benefit from using this study’s well-researched self assessment strategies to re-energize learning for their students.