After graduating high school, Attorney Sullivan, like his father and both grandfathers before him, joined the military in order to help pay his way through college. After a decorated tour of duty in Iraq during Operation Desert Storm in 1991, Attorney Sullivan finished his undergraduate studies as a Social Work major at Bridgewater State University where he graduated in the top 20% of his class. Soon realizing that he could only accomplish so much helping others as a Licensed Social Worker, Attorney Sullivan decided to apply to Law School. He was one of only 230 people, from a pool of 3,400 applicants, to be admitted to the New England School of Law in Boston. Attorney Sullivan worked full time as a Corrections Officer and later as a Licensed Social Worker throughout both his undergraduate studies and during Law School. Nevertheless he managed to finish his first year of law school within the top ten students of his class, earning him an editorial position on the prestigious New England Law Review, and he graduated Cum Laude, earning recognition as a New England Scholar, in 1998.