Abstract: This paper proposes a framework for analyzing 21st century teaching/learning attentive to implementation and educational reform. While teaching, curriculum, school cultures, school structures and support for schools require revisiting assumptions to improve student learning as we move through the 21st century, gaps exist in calls for implementing 21st century learning. Based on this writer’s experiences working in schools as educator and technology professional, an exploratory framework to assess implementation of 21st century learning by considering educational value, benefits and economic plausibility of proposed changes is proposed. This paper contributes a preliminary review of the literature with a summary of a number of 21st century positions, with a framework to assess implementation by considering new literacies, digital divides, teacher training, and curriculum reform. Given the foundational nature of the framework proposed, this paper carries implications for administrations, technology support professionals, district coordinators, teacher educators and classroom teachers.