Sharon Rose "Sheri" Simon was born April 14, 1961, in Garfield Heights, OH, to John and Lois Ann Simon. Her parents were divorced (ca. 1968), after which she lived with her mother and then was adopted by an older half brother. She graduated from high school in 1979, the same year she received the Louis Armstrong Jazz Award. She attended college at Lake Erie College and graduated in 1983 with a B.A., majoring in the Physician's Assistant course. Simon was converted during her sophomore year of college (1980-1981).

During her junior year of college, Simon worked on a short-term basis in a clinic in Mexico to fulfill a graduation requirement; her assignment included classes and work in a clinic supervised by a Mexican doctor. Her experience convinced her to find similar work on a long-term basis. After graduation, she worked at St. Vincent Charity Hospital in Cleveland, OH. Between July 1984 and July 1986 she worked as a medical volunteer with the support of her home church in the Hospital Bon Samaritain in Limbe, Haiti. While in Haiti, Simon witnessed the revolution against and departure of dictator Jean Claude Duvalier, as well as the aftereffects of that political crisis. In the fall of 1986 she returned to Wheaton, IL, to study at Wheaton College Graduate School in the Missions/Intercultural Studies program.

At the time of the interview, Simon was enrolled in the Graduate School in order to complete candidacy requirements of the American Baptist Foreign Missions Board. She discontinued her studies for health reasons at the end of her first semester. In July 1987 she married Rich Roby. The Robys accepted a one-year appointment at the Hospital Bon Samaritain in 1988, where they worked until mid-1989, after which they returned to the United States. During their year in Haiti, the Robys adopted an infant Haitian girl, whom they named Georgette.