Images in contemplative practice turn on a seeming contradiction: they can serve as guides on the mystical path but can easily become obstacles as well. On October 10th, 2021, I met with Don Salmon on Zoom, as the two of us shared our experiences and ideas about the promises and pitfalls of using images to deepen our connection to God. This piece, which is based on our conversation, explores the contradictions inherent in our use of images for spiritual guidance, along with questions related to the intersection of art and theology. We discuss whether abstract images or images of nature have the same power to inspire contemplation through devotion and love as sacred images of specific mystics, yogis, sages, and saints. Whether there is a difference in the state of consciousness achieved through religious tradition as compared to contemporary methods of spiritual practice that aren’t necessarily associated with a tradition, and the role of imagery in devotional practices vs non-devotional practices. We explore the relative value of image-based vs. non-image-based meditation, and the benefits of using digital images for contemplation. We also discuss the nature of apophatic and cataphatic methods and how different traditions approach images as vehicles for spiritual enlightenment.