[1] In 1996 and 1997, she did a year of Ph.D. coursework in English literature at CUNY Graduate Center, before dropping out to study writing at Columbia University, where she completed her MFA in 1998.

[1] In 1996, aged 23, Rakoff took a job at one of New York’s oldest literary agencies, Harold Ober Associates.

In her time at the agency Rakoff's responsibilities included responding to the large volume of fan mail that Salinger received.

Rakoff was instructed to respond with a generic response that explained that Salinger did not read fan mail.

It received largely positive reviews and was included on many Best of 2009 lists, including NPR, Elle and Booklist, and was awarded the Goldberg Prize for Jewish Fiction by Emerging Writers,[3] an award previously won by Gary Shteyngart, Nathan Englander, and Laura Vapnyar.

The book was turned into a 2020 Canadian film of the same name starring Margaret Qualley as Rakoff and Sigourney Weaver as her boss, directed by Philippe Falardeau.

Prior to publishing A Fortunate Age, Rakoff worked as a freelance literary journalist and critic, contributing frequently to the Los Angeles Times, the San Francisco Chronicle, Newsday, the Guardian, and the New York Times, as well as magazines like Vogue, Marie Claire, and O, The Oprah Magazine.