In 1971, he co-founded Crossroads School in Santa Monica and built it into one of the most successful educational institutions in Los Angeles and a national model for innovative, independent, progressive schools.
In 1995, Cummins stepped down as headmaster of Crossroads and formed New Visions Foundation (now Coalition for Engaged Education) to offer opportunities for Engaged Education to all youth. The first venture was New Roads School, a diverse, K-12 independent school in Santa Monica that has a deep commitment to social justice. New Roads devotes 40% of its tuition budget to need-based student financial aid, guaranteeing access to students from a wide socioeconomic array. Cummins has since co-founded several other schools, including Camino Nuevo Charter Academy, LAAAE, and New Village Girls Academy and implemented a number of innovative programs, such as P.S. Arts, to help vulnerable children and youth.
Cummins has published four books on education, including For Mortal Stakes: Solutions for Schools and Society (1998), Proceed with Passion: Engaging Students in Meaningful Education (2004), and Two Americas, Two Educations: Funding Quality Schools for all Students (2007). Other recent publications include a book of essays, Why Poetry? Reflections on Poetry, Writing and Culture, as well as two volumes of original poetry and two children's books. His professional autobiography entitled Confessions of a Headmaster, will be released from Red Hen Press in October 2015. Meanwhile, Cummins is at work on a new book entitled Engaged Education.
Cummins and his wife Mary Ann reside in Santa Monica. They have four daughters and five grandchildren.