Following the launch of the positive psychology movement teachers and educators emerged as early adopters of this fledgling science. This approach was called positive education. It describes scientifically validated programs from positive psychology, taught in schools, that have an impact on student well-being. The growing body of evidence about the reach of positive psychology has formed a convincing case to consider well-being an operational goal for educational systems. It is argued that this goal is pivotal and should be pursued in the same way in which we develop strategies to harness academic growth, school retention rates, and student engagement. National education policies can have widespread influence at the grassroots level on school improvement, good quality of classroom teaching and learning, student performance, creating confident and creative individuals and active and informed citizens, but not necessarily on the preventative skills for lifelong well-being. In this article I take stock on the positive education movement. Three approaches to positive education are identified and eight hurdles to the field are noted as reasons why positive education won’t stick in policy. Then, I reflect on two case studies: a Well-being Summit and Round Table held at Wellington College and No. 10 Downing Street and Dr. Martin Seligman’s role as Adelaide’s Thinker in Residence as examples of grass-roots initiatives in well-being. Finally, six strategies are suggested for researchers and practitioners to grow the field. Last, I argued that until research centers focus on the development of common definitions of the key terms underpinning positive psychology, positive education and well-being the impact of the movement will be limited to a handful of institutions as models of best practice.