Grey was a social studies teacher when she moved from Baltimore to Portland in the mid-1960s. She worked for several years in alternative education, including as part of the Portland Learning Community. In the late 1970s, she bought (with her then-partner) the Genoa, where she was also a chef. In the 1980s, she and three partners started Bread and Ink Café. 

For the last four decades, she was a therapist, working with individuals and couples. Grey's full and thriving therapy practice was at the center of her life. 

On the morning she was hit and killed by a car at 37th Avenue and Cesar Chavez, she was returning from her daily walk to Mt. Tabor and planning on seeing her first client at 8:30am.