Change always catalyzes organizational members to challenge, reframe, and revisit the assumptions that preside over the work they do. But how do recent changes affect individual and collective organizational transformations? More fundamentally, how can we think about learning and transformation in an organizational environment in perpetual transformation? In this article we examine trends impacting organizations in light of recent thinking by transformative learning scholars interested in organizational change in the midst of complexity. We also revisit our dual approach developed 10 years ago and speculate on an emerging integrative framework for individual and collective transformation better suited to the years to come.