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A key aspect of promoting innovation in schools is understanding how and why innovators are motivated to innovate. However, even in the emerging literature on motivating innovation, there is a paucity of information on established innovators’ motivations for innovating. This primarily qualitative study addresses this knowledge gap by investigating the strategies that innovators used to make innovation more likely, combining 30 semi-structured interviews and a survey of 500 Canadian innovators. Innovators detailed advice and approaches for aspiring innovators to maximize expectancies, maximize values, and proactively mitigate costs. This study calls for a reconceptualization of innovation education to focus on building capacity for developing innovators based on the strategies of successful innovators.