Shear came to prominence with her self-penned solo performance piece "Blown Sideways Through Life" (described by Frank Rich as an "autobiographical monologue"). The show premiered at the New York Theatre Workshop in September 1993. The show then opened at the Off-Broadway Cherry Lane Theatre on January 7, 1994, closing on July 17, 1994 after 221 performances. Shear won an Obie Award, Special Citation and a 1994 Drama Desk Award nomination for Outstanding Solo Performance. Shear's employment experiences as a member of the American work force - sixty-four jobs in all, including pastry chef, nude model, waitress, whorehouse receptionist, proofreader, and Italian translator - provided her a wealth of material for her piece. She adapted it for a 1995 presentation on the PBS series "American Playhouse".