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This chapter offers a theoretical framework to explore the relationship between resilience, wellbeing, and authentic leadership through the students’ transition from high school to university. It highlights how student leaders can thrive despite the challenges they face throughout this transition. First, the author presents an overview of resilience research, specifically by defining key characteristics of resilient students, followed by the outline of the four waves of resilience research. Next, the author describes the construct of wellbeing and the common characteristics among the wellbeing models in relation to the general university student population, as well as student leaders. Next, the author reviews the authentic leadership theory, including its key components of authentic leadership, the psychological capabilities for authentic leadership, and how resilience manifests in authentic leaders. The author concludes with an overview of transitional periods, critical life events, and their manifestations in the transition from high school to university.