Positive education, a unique blend of academic learning and positive psychology theory on well-being, is becoming increasingly important in today’s educational system, as mental disorders like anxiety and depression continue to increase in schools. Located in Bryn Mawr, Pennsylvania, The Shipley School, an independent PK-12 school, is an early adopter of positive education. In August 2017, Shipley led a three-day positive psychology retreat for all of its colleagues (teachers and staff); 25 self-selected colleagues, known as trained trainers, received an additional two days of training to guide them towards becoming thought leaders at Shipley. Preliminary evidence suggests that student’s perceptions of their teachers’ well-being may be associated with student well-being at Shipley. Additionally, the positive psychology retreat seems to have enhanced positive relationships among colleagues while decreasing loneliness and negative emotions. Per colleague feedback, active constructive responding, gratitude, mindfulness, optimism/thinking traps, and strengths appear to be the most salient skills taught at the retreat. As a result, we have developed onboarding plan recommendations for new colleagues encompassing the teaching of these five skills in small-group settings led by the trained trainers. We believe that Shipley is well on its way to becoming a leading model for positive education.