Calegari is a veteran public school teacher who has had ten years of classroom experience. She holds a master's in education in teaching and curriculum from Harvard University's Graduate School of Education. In 2005, Calegari co-authored a call-to-action book called Teachers Have It Easy: The Big Sacrifices and Small Salaries of America's Teachers. Presently, she is working with an Academy-Award winning filmmaker to produce a documentary to tell America's teachers stories.
Calegari has been appointed as an advisory board member of the George Lucas Educational Foundation and a San Francisco Arts Commissioner. She is also the recipient of Edutopia's 2007 Daring Dozen award for being among twelve people "reshaping the future of education."