Self-directed Learning (SDL) is recognised as one of the critical 21st Century skills for life and career (Partnership for 21st Century Skills, 2011). As advances in technology increase the pace of change and the shelf life of knowledge decreases, students have to have more than thinking skills and content knowledge. They have to develop the skills sets and mindsets to be able to learn independently so as to be able to adapt to a constantly changing world. With the various definitions in mind, Singapore Polytechnic (SP) proposed a SDL model that involves 2 key components: Motivational or mindset component and Cognitive or skills set components. In this paper, the authors will describe the SDL model and will explore the extent to which flipped learning provide students with opportunities for self-directed learning. The paper will also detail a study, involving both qualitative and quantitative methods involving 4000 students, conducted to ascertain the impact of flipped learning on students’ self-directed learning. The paper will present the analysis of the quantitative data findings of the study and the learning and future work that emerged.