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 continued to write for
The Nation from Israel in 1956, becoming a staff writer for the magazine on his return the same year. He also published in periodicals such as
Dissent,
Commonweal,
Commentary,
New World Writing,
Harpers,
Esquire,
The Atlantic,
The Yoga Journal,
GQ and
TV Guide. Wakefield was listed as a "sponsor" for the
Fair Play for Cuba Committee in its manifesto. 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". After his year as a
Nieman Fellow, he moved to
Beacon Hill in
Boston, where he began writing for
The Atlantic, writing the entire issue of the magazine for March 1968, called "Supernation at Peace and War", which then was published as a book. From 1968 to 1981 he was a contributing editor of
The Atlantic). In November 2011, Wakefield returned to Indianapolis to speak on a panel discussion of the work of Vonnegut at the Vonnegut Library and Museum . A month later, he moved back to Indianapolis permanently, thus contradicting Vonnegut's prediction in his review of
Going All The Way in
Life magazine: "Having written this book, Dan Wakefield will never be able to go back to Indianapolis. He will have to watch the
500 mile race on television". After moving back, Wakefield was inducted into The Indianapolis Public Schools Hall of Fame, The Shortridge High School Hall of Fame,
The Indy Reads Literacy Leaders Hall of Fame, and received a Cultural Vision Award from the news weekly
NUVO. On June 1, 2016, the neighborhood park at 61st and Broadway Street in the Broad Ripple neighborhood of Indianapolis, Indiana, was renamed Dan Wakefield Park. Wakefield taught writing at the
University of Massachusetts at Boston,
Emerson College,
Boston University,
The University of Illinois Journalism School and The Iowa Writers Workshop. He edited and wrote the Introduction of the letters of his friend and fellow Shortridge High School graduate
Kurt Vonnegut (
Kurt Vonnegut Letters) as well as a collection of Vonnegut's graduation speeches and other related pieces (''
If This Isn't Nice, What Is?: Advice to the Young''). Wakefield retired as writer in residence at
Florida International University (1995–2009), where he received The Faculty Award for Mentorship. ==Personal life==