This chapter weaves together ideas of coming to art as a personal practice, a family history of medical childbirth, and stories of participating as a doula-grandmother while attending two natural midwife-births in Chile. Using five paintings from dreams and imagination, the author interlaces several perspectives, including a Jungian approach to art, birth anthropologists, the medical and midwifery models of birth, and the historical repression of midwifery in the United States. Psychoanalytic writing, such as Jung’s concepts of the “shadow” and “inflation” as well as Winnicott’s “facilitating environment,” add a deeper understanding of the midwifery model in practice. In conclusion, the author reflects on the value of art in preparation for childbirth and how body memory of “warmly held” births can facilitate such experiences.