Students of organizations are beginning to recognize the importance of continuous learning in organizations, but to date the concept is not well understood, particularly in terms of how the learning of individuals is related to the learning that takes place in groups, which is related to the learning that occurs in organizations (and all other combinations). To further our understanding, we offer the idea of continuous learning in organizations from a living system's perspective. We view individuals, groups, and organizations as living systems nested in a hierarchy. We propose that living systems can learn in three ways: they can adapt, they can generate, and they can transform. Learning triggers from the environment spark learning, and this relationship is moderated by the system's readiness to learn. Readiness to learn is a function of the permeability of the system's boundaries, the system's stage of development, and the system's meta-systems perspective. Additional research questions are presented to explore learning flow between levels and to determine how the match between one system's pressure for change and another system's readiness to learn affects the emergence of adaptive, generative, and transformative learning. In addition, research questions are offered as a means to test these ideas and build grounded theory. Finally, using this model, the chapter presents three case studies and suggests diagnostic questions to analyze and facilitate continuous learning from a multi-level perspective.