Simon was born into the world of the arts. His father, Sidney Simon, was a sculptor, and his mother, Joan Crowell, is a writer and composer. Their home resonated with discussions of art and music, inspirations that led Simon to major in sculpture at college. After graduating cum laude in 1968 from Brandeis University, he switched to architecture. Being naturally gregarious, he felt he would be happier working with other people and that architecture might touch more varied lives than sculpture.
After graduating from the Yale School of Architecture in 1972, Simon initially built cabinets and houses, but returned to work in several architecture offices, and was soon hired by Charles Moore, his former teacher and dean at Yale. They collaborated on a number of unique homes, and Simon was named as a partner at Moore Grover Harper, which eventually became Centerbrook Architects.
From the start of his career, Simon has been a pioneer in the practice of “green” architecture, beginning with his design in 1973 of an “Earth House” that was built into a hillside and decades later continues to take advantage of the clean heating and cooling energy of terra firma. Today Simon’s practice ranges from private houses and highly crafted furniture, to commercial, institutional, academic, and religious projects. He continues to develop groundbreaking classroom and science buildings for independent schools like Pomfret, Berkshire, Liggett, and University School. He has designed many landmark buildings, among them: LancasterHistory.org in Pennsylvania; Nauticus – The National Maritime Center in Virginia; Park Synagogue East in Ohio, the Chemistry Building and Business School at the University of Connecticut; Yale’s Kroon Hall (with Hopkins Architects); the Yale Cullman-Heyman Tennis Center; Kenney Center and Jensen Plaza at the renowned Yale Bowl; and Lakewood House in the Northeast.
Simon's innovative design has been noted by Time Magazine, The New York Times, among others. His 112 architectural awards include the prestigious American Institute of Architects Architecture Firm Award that Centerbrook received in 1998. In 1990, he was inducted into the American Institute of Architects College of Fellows.