Many institutions of higher education claim to produce leaders and many assume that graduating from a university equates to someone naturally growing in their ability to lead. Developing leaders is considered a worthwhile endeavor in society today and developing a leadership identity is considered foundational to leadership development in college. While colleges and universities purport to develop leaders, little is known about how best to help students develop sustainable leadership learning. Utilizing design-based research, this study examined the learning experiences of college students in three different semesters of a personal leadership course through their reflections about course activities designed to help them develop their leadership identity. Using network maps from student reflections, we analyzed the complexity of learner experiences and developed a set of design principles anchored in the relationships between learning experiences concerning strengths, weaknesses, and theoretical foundations. The following design principles emerged from this study: framing for authentic learning, scaffolding for learner agency, social and collaborative learning, and multimodal engagement. By using these principles in designing leadership experiences, college leadership educators will be empowered to create opportunities that are sustainable and inclusive and that promote lifelong learning in regard to students’ authentic and personal leadership development practices.