This study was conducted to develop a grounded theory of connections between individual and collective (group and organizational) levels of analysis through the examination of play and sense-making as integral parts of organizational learning (OL) by relying on the meta-paradigm theoretical framework. The study employed grounded theory as its methodology, and its participants included 23 employees of Company A, a U.S. consulting company, who were selected using purposeful maximum variation criterion-based sampling. One semi-structured 30-60-minute interview was conducted with each participant by phone or face-to-face. In this study, OL took the form of sense-making through play that was a social and linguistic process of organizing the information flux and coping with uncertainty that expanded knowledge and practices within the organization. The source of flux and uncertainty was the interaction of multiple social worlds and sub-worlds (such as Company A, its project teams and clients, partnering organizations, etc.) that disrupted practices and discourses within them. Uncertainty and information flux caused confusion, discomfort, anxiety, and stress in individuals, who paused in order to bracket the flux and suspended existing knowledge, discourses, and practices. Individuals then created new knowledge, practices, and discourses while developing intersubjectivity, and validated them with multiple social worlds. The results of OL as sense-making through play were captured in collective practices that linked knowledge and action and incorporated multiple social worlds. OL as sense-making through play occurred in the ludic space of sandbox, or a physical, social, and mental space that brought together work and play, and had a dichotomy of stability and change. OL as sense-making through play had four dimensions (intuition, improvisation, experimenting, and having fun) that were responses to specific situations of the interaction of social worlds. These dimensions reflected the dichotomies of tacit and explicit knowledge and their exploration and exploitation, and shared several characteristics (situatedness in the interaction of social worlds, adaptive instantiation of other social worlds, leaping between social worlds, abductive thinking, and focusing on results). The connections between the levels of analysis of OL as sense-making through play were non-linear, multi-directional, and situationally-specific with discontinuities and interruptions so that individual sense-making through play did not necessarily become collective. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]