Through an inductive study of Learning and Development (L&D) executives in 69 multinational organizations, the authors build a theory of marginal leaders’ conception of learning in organizations. As marginal leaders, L&D executives lacked an established template for their leader identity and had to navigate conflicting prescriptions for their function. The conception of learning - a process that involved finding a place in relation to significant counterparts, taking a stance on learning, and building learning spaces - allowed them to craft identities that gave meaning and direction to their work, grounding their identity as leaders. Not all marginal leaders took the same trajectory towards firm ground for their identities. Some left the margins to lead, embracing either an instrumental or a humanistic view of their function. Others learned to lead from the margins, casting that duality as a paradox. Taking a systems psychodynamic approach to examine marginal leaders’ trajectories through a defining duality, this study reveals the interplay between existential and strategic layers of leader identity construction. Theorizing the conception of learning as the process through which leadership comes to life and gets organized, the study expands and bridges the literatures on leader identity and on the management of dualities.