Kennedy began her education with kindergarten classes in the White House organized by her mother. Before the family's move to New York, she was registered at Stone Ridge School of the Sacred Heart. She attended The Brearley School and Convent of the Sacred Heart in New York City and graduated from Concord Academy in Massachusetts in 1975. She was a photographer's assistant at the 1976 Winter Olympics in Innsbruck, Austria. In 1977, she worked as a summer intern at the New York "Daily News", earning $156 a week ($673.41 in 2019 dollars), "fetching coffee for harried editors and reporters, changing typewriter ribbons and delivering messages." Kennedy reportedly "sat on a bench alone for two hours the first day before other employees even said hello to her"; and, according to Richard Licata, a former "News" reporter, "Everyone was too scared." Kennedy also wrote for "Rolling Stone" about visiting Graceland shortly after the death of Elvis Presley.