Rawley earned his MD upon graduation from Johns Hopkins in the mid-20th century after he was educated at Harvard University. He then spent some of his four years after graduating from Johns Hopkins in France and England as well as in Vienna. During his stay in these countries, he studied psychiatry.
He then worked for six months at the Hendler's Sanitarium where he met the patients Charles and Serena Wilson. Rawley moved to the city to take up a position as junior analyst to an "almost legendary" analyst. He became dissatisfied when he realized that he was helping the needs of the elite and wasn't spreading the benefits of psychiatry to a larger body of people. Faced with limited options in the city, Rawley decided to stake his future in psychiatry by purchasing country doctor Jenkins's practice in Berkshire County. There, he could heal his patient's mental health while tending to their physical needs. Upon settling matters, Dr. Rawley quit his position as junior analyst and headed to Fairbridge. (TNG: "The Big Goodbye")