Her first foray into politics occurred in 1998, when she ran for state representative in the 6th Essex District – representing her hometown of Beverly, Massachusetts – challenging incumbent Democrat Michael P. Cahill. After losing the heavily democratic district in 1998, Healey challenged Cahill again in 2000, but was met with the same result. After Healey's loss in 1998, she was elected to the Republican State Committee. Next, Healey taught social policy as an adjunct professor at Endicott College in 2001.