How do different traditions envisage the relationship between inner transformation and active compassionate outreach toward our neighbor’s needs? In the Philokalic tradition, early authors from the Evagrian school appear to posit the primacy of contemplation (theōria), viewing the practice of the virtues as a largely preparatory step toward the achievement of an inner attitude of detachment (apatheia). Later authors such as Maximos the Confessor (580–662), who write in the wake of the Chalcedonian Christological settlement, tend instead to envisage theōria and praxis as two mutually complementary aspects of the spiritual trajectory of the individual. In the Tibetan tradition, the spiritual master Tsong kha pa (1357–1419) develops his vision of the spiritual life on the basis of the Mahāyāna teaching of apratiṣṭita (active) nirvāna, which is significantly different from the earlier Theravada understanding of the awakened state. Rather than a flight from embodiment and the senses, this approach views enlightenment as flowing from the simultaneous pursuit of contemplation and the practice of the virtues (paramitās). This chapter develops a conversation between these two approaches, underscoring the points of contact, but also the differences between their respective anthropologies and understandings of spiritual practice.