In this paper, the author explores some preliminary steps towards designing a large classroom environment that supports the development of three aspects of character that lead to lawyering effectiveness: self-development, passion and engagement, and stress management. The paper proceeds in three parts: (1) the author provides an illustrative example of the joys of transformative learning; (2) the author explores a sample of three character attributes required by law students on graduation, and situates those attributes in the literature on legal education; and (3) the author offers concrete teaching technologies that might be employed to advance those character behaviours in students and provides an assessment of their effectiveness in the large tax law class the author teaches most years.