We continue to explore the role of working with transforming psychological conditioning and unresolved material (incomplete developmental tasks, developmental wounds, trauma, limiting beliefs, etc.) in a contemporary path of awakening. Using the concepts of unconscious material and of the “shadow” (individual and collective), we point to how the Buddha faced his own shadow (the four heavenly messengers that he found outside of his conditioning in the palace). We then explore some tools and ways to open to and work with unconscious or shadow aspects of ourselves, both in and out of formal meditation.