Academic pursuits are inseparable from the medium within which they take place — life. The lives of medical trainees can present many challenges that are independent of academic demands. Poor psychological health has been found to develop in medical trainees. Can medical educators minimize this decline in well-being? Positive education — learning skills for traditional academia and to foster happiness — has been shown to improve students’ well-being. This piece considers the application of ‘positive education’ to medical training. By using this approach, we may optimize the lives of our trainees, potentially enhance learning and improve their academic and personal outcomes.