 For high school, Calegari went to Santa Catalina School and graduated in 1989, later going to Middlebury College to receive her bachelor's degree in 1993 and a Masters in Teaching and Curriculum from the Harvard Graduate School of Education in 1995.She worked at Leadership High School, San Francisco's first charter school, where she also served on the Board of Directors, and then taught in her family's hometown in Mexico.Calegari was a co-founder of 826 Valencia in April 2002 and the founding executive director.