In an era of high stakes education and the persistence of racism, classism, and the politics of language, there is evidence that teachers may benefit from learning creative insubordination, the bending of rules in order to advocate for all students to learn mathematics. Even so, we know little about how or why teachers decide to take risks when stakes are high. This study examines the experiences of secondary mathematics teachers moving from pre-service to full-time teaching and their choices of whether or not to use creative insubordination in their working contexts. It highlights three rationales that justify taking risks: 1) Changing the minds/practices of others, 2) Projecting an identity one can be proud of, and 3) Modeling advocacy behavior for bystanders. Implications for future research and teacher education are offered. [For the complete proceedings, see ED583989.]