This paper describes a two-year supervision by Skype with a candidate in China enrolled in the China American Psychoanalytic Alliance's psychoanalytic psychotherapy training, and an analyst in the USA in which the young analyst in training struggles with her career choice. The candidate has a dream about her choices disguised as a car journey and also dreams about the supervision, evidence that a strong relationship with its transference-countertransference implications can exist even via Skype across 8,000 miles.