Freeland completed a bachelor's degree at Harvard University, studying Russian history and literature before earning a master's degree in Slavonic studies from the University of Oxford. She worked as a journalist in Ukraine and eventually held editorial positions at the Financial Times, The Globe and Mail and Reuters, becoming managing director of the latter. She also authored Sale of the Century: Russia's Wild Ride from Communism to Capitalism (2000) and Plutocrats: The Rise of the New Global Super Rich and the Fall of Everyone Else (2012).