In “The Quest for Wisdom and Human Flourishing” class, students study diverse aspects of wisdom, practice living wisely by following a different ancient Greek philosophy each week, and reflect on their experiences in writing and weekly discussion sessions. To test whether we were able to plant the seeds of transformational wisdom in students, four wisdom scales (SD-WISE-7, SAWS, 3D-WS, and ASTI) that measured different qualities of pre- and proto-transformational wisdom were assessed at the beginning and end of the spring semester in 2023–2025 in three wisdom classes (n = 218) and six comparable control classes (n = 308). Repeated measure MANCOVA (controlling for dichotomized race) indicated a significant interaction between time and type of class for the combined wisdom measures. Follow-up repeated measures ANCOVAs showed significant increases in all four wisdom measures in the wisdom classes but no significant changes in the control classes between the beginning and end of the semester. A qualitative thematic analysis of 56 students’ final papers of the 2024 wisdom class revealed that students believed they grew in wisdom in areas related to self, other, and reality. Regarding obstacles encountered during the class, students realized that following Greek philosophies was not easy. Other challenges were an unwillingness, inability, or struggle to follow certain aspects of the philosophies, mental and physical health difficulties, and lack of commitment. When asked how they intended to apply the insights they gained to their future professional career, students reported that they planned to identify wise leaders and wise organizations and positively impact their professional career, place of work, and society.