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This study explored pre-service teachers’ (PSTs) motivation obstacles and patterns of motivation regulation strategies to address them within major area courses and practicum. Interviews with six PSTs afforded access to novel obstacles and a wide range of motivation regulation strategies employed in career-relevant contexts. Analysis of two cases illustrate contrasting motivational obstacle-regulation profiles. While students reported some common obstacles (i.e., high effort cost), Penny faced the substantive obstacle of low attainment value, questioning her future as a teacher. In response, Anne intentionally engaged in mastery self-talk and connected to her future goal of teaching, whereas Penny relied on extrinsic utility focused on completing coursework. Findings showcased students applying distinct strategy combinations differentiated in quality.