with Honors in English, after having studied with the literary critics Mark Van Doren and Lionel Trilling, as well as the sociologist C. Wright Mills.
After college, Wakefield worked as a reporter at The Princeton Packet, New Jersey's oldest weekly, which he later left to become a research assistant for the sociologist C. Wright Mills, his professor at Columbia.
His research duties left him time to begin his career as a freelance journalist, covering the Emmett Till murder trial in Mississippi for The Nation magazine.
He also published in periodicals such as Dissent, Commonweal, Commentary, New World Writing, Harpers, Esquire, The Atlantic, The Yoga Journal, GQ and TV Guide.
On publication of his collection of articles and commentary Between The Lines (1966), The New York Times said he was "acknowledged to be one of the country's most perceptive and sensitive independent commentator-reporters".
During college, Wakefield became an atheist and did not return to church until 1980 when he went to a Christmas Eve service at King's Chapel, a Unitarian Universalist congregation in Boston.