Stefanie Siegel was born in Worcester, Massachusetts in 1951. She attended high school in Maryland, and after a decade of working and searching for the right opportunities, she attended Reed College in Portland, Oregon. She also has degrees from the University of Chicago and the City University of New York. Siegel began teaching English in the New York City Public School System in 1987. After teaching at Brooklyn's Erasmus Hall High School for a time, she began teaching at Paul Robeson High School in 1991. In addition to teaching there, she was the Coordinator of Student Affairs/Senior Advisor and joined a student-led group organized to save the school from permanent closure. Siegel founded Bailey's Cafe in 2002. The organization, which she also heads as Executive Director, is built on a doctrine of intergenerational learning. After a fundraising campaign, the non-profit moved to a permanent home at 324 Malcolm X Boulevard in the Bedford-Stuyvesant neighborhood of Brooklyn in 2015.