The purpose of this action research study was to better understand how aspiring school leaders orient themselves toward present and future uncertainty and to explore what mindsets and conceptual understandings they believe they need to lead through uncertainty. An innovation, delivered through a graduate course on leading change in a Master of Educational Leadership program, focused on supporting participants’ mindsets and conceptual understanding toward leading change in the midst of uncertainty, including the COVID-19 global pandemic. A total of 34 students participated in this qualitative case study. The educational innovation was designed by this action researcher and was informed by transformative leadership theory, design thinking, and imagination. Four sources of data were used to answer the research questions, including students’ written assignments and video reflection assignments, as well as researcher course observations and semi-structured interviews with participants. Major findings suggested that the educational innovation was effective in supporting participants identity development as transformative leaders, as well as supporting participants’ adoption of design thinking mindsets and use of imagination as tools for leading change in complex systems and during uncertain times.