It is well documented that Japanese students of English as a foreign language (EFL) often struggle to find meaning in their learning. In a field dominated by quantitative studies on motivation and demotivation, few studies have examined how strategies that connect learning to self-concept might have positive effects on motivation from students’ perspectives. Similarly, whilst many recent studies have explored the L2 Motivational Self System, a notion of language learner motivation built around the interaction between learners’ self-concepts and the environment (Dörnyei, 2009a), few have focused on the application of this model to improving educators’ understanding of the classroom learning experience and improving its quality. This research approaches the study of classroom EFL learner motivation from a complex systems perspective. Working from the lived experience of the participants, it uses action research methods to explore the dynamic conditions operating in the foreign language classroom. Complex systems theory is used as a lens through which to examine the interplay between learner-internal and -external elements and their effects on motivation. Drawing on contemporary psychological research into the use of possible selves as a powerful motivational tool, this study investigates the ways classroom environments involving activities that connect learning to future self might encourage students to articulate the complex conditions affecting their motivation to learn English.