The information explosion characteristic of a knowledge-based economy is fuelled by rapid technological changes. As technology continues to permeate our lives, there will be fresh demands upon the conduct of learning and teaching to ensure that learners are equipped with new economy skills and dispositions for creating significant and relevant meaning out of the large chunks of transmitted data. In the spirit of building learning organisations, this paper proposes that a two-pronged strategy of promoting self-organised learning (SoL) amongst educators and students be adopted. As an enabling framework based on social constructivism, the model of SoL, originally developed by Harri-Augstein & Thomas, is described and applied to an educational setting. For educators engaged in action research, SoL is suited as an approach for managing and reflecting upon change. The use of two such thinking tools, the Personal Learning Contract and the Purpose-Strategy-Outcome-Review (PSOR) reflective learning scaffolds are considered. For students who are now expected to learn independently in situations requiring problem-solving skills, much akin to real life contexts, this article also considers the application of Learning Plans as a conversational tool for personal project management. The authors conclude that SoL promotes skilful critical thinking through a systems thinking process of continuous reflective learning. It is proposed that these are essential qualities for citizens working in a technological age. Case study samples of the thinking tools used in this action research project are included as appendices and evaluated in this article.