Theoretical frameworks, field experiences and survey data underscore a consistent and compelling message of the need for both deliberate planting and organic growth for cultivating student (and staff) well-being in high performing schools. Theoretical models lay a foundation for establishing teacher competency, autonomy (Deci & Ryan), agency (Biesta) and well-being knowledge (Seligman) as necessary for growing positive education. Insights of leading practitioners (White & Murray) confirm the essentiality of these factors as well as institutional commitment. Staff survey data verifies the importance of staff knowledge, autonomy/agency and institutional commitment as an essential three-part framework (Cohen) for promoting well-being and performance in high achieving schools. Moreover, our data together with insights theory and practice insights provides guidance for cultivating well-being through intentional strategies AND organic growth processes related to these factors. Intentional cultivation strategies include promotion of (1) staff knowledge: targeted opportunities for staff to learn about well-being (2) institutional support: clear mission statements, goals, funding and program supports that establish well-being as a transparent district priority. Organic growth strategies include supporting and encouraging independent teacher study, voice and creativity in developing approaches and lessons that foster well-being. Student flourishing is best cultivated through both intentional planting and organic growth.