In this article, we argue that virtues can emerge from contemplation which can lead us to attunement with the Dao thereby realizing our inner goodness and intrinsic traits. This requires us to persist in doing inner and outer work. Inner work involves meditation and reflective practices to awaken ourselves and others. Outer work involves engaging others and ourselves with loving-kindness, compassion, joy, and equanimity. The article discusses the transformative perspectives and practices in Daoist, Confucian, and Buddhist contemplative traditions that lead to the development of virtue and alignment with the Dao; further, it examines contemporary contemplative practices and new scientific discoveries, providing evidence that virtues of a leader can emerge from within. In other words, virtues can be cultivated, and there are rich traditions and methods in both Western and Eastern philosophies and religions that facilitate the emergence of virtues through contemplative and other religious practices. Character building and virtue training are linked to inner contemplative work, which we argue need to be integrated with cultivating vital life energy and doing good for the world. Character education and transformation are much more effective when supported by contemplative practices and inner work because changes come from deep within the heart. The integration of these two elevates our awareness of our interconnectivity with all and enhances our ability to serve the world lovingly and humbly, which are hallmarks of virtuous behaviors.