Chapter 2 How do Mindfulness and Routines Relate? Metacognitive Practice as Resolution to the Debate Ravi S. Kudesia and Tingting Lang Abstract Routines are the very material of human organization. But there is little guarantee that routines will be enacted fexibly enough to ensure that or- ganization survives. Mindfulness has been offered as a guarantor of sorts, but it remains unclear exactly what people mean by mindfulness and how mindfulness might relate to routines. This chapter reviews evolving con- ceptions of mindfulness and routines—from Langer’s early work to rou- tine dynamics to Levinthal and Rerup’s seminal debate with Weick and Sutcliffe. It puts forth the argument that the recent theory of mindfulness as metacognitive practice retains important insights from throughout this conceptual evolution, while resolving ambiguity and debate about the rela- tion between mindfulness and routines in at least four critical areas related to agency, duality, fexibility, and social organization. This resolution, in turn, opens up further avenues to understand the social processes by which people come to understand their minds—and how this understanding em- beds within organization itself. Keywords: Mindfulness; metacognition; routine dynamics; practice theory; social organization; agency Introduction What does it mean for people to organize—and achieve some degree of organi- zation as a collective? Ultimately, it means that their individual actions have Thinking about Cognition New Horizons in Managerial and Organizational Cognition, Volume 5, 9–29 Copyright © 2022 by Emerald Publishing Limited All rights of reproduction in any form reserved ISSN: 2397-5210/doi:10.1108/S2397-521020210000005002