Chollet started in Washington in 1993, when he was the research assistant to former secretary of state James A. Baker III helping him with his memoir, The Politics of Diplomacy. In 1996, he was asked by the State Department to write a comprehensive history of the Dayton Peace Accords, which was declassified in 2003.[11] In 1999 he joined the Clinton Administration, where he served as chief speechwriter for UN ambassador Richard Holbrooke and as special advisor to deputy secretary of state Strobe Talbott. From 2002 to 2004, Chollet was foreign policy adviser to U.S. senator John Edwards (D-NC), both on his legislative staff and during the 2004 Kerry-Edwards presidential campaign. From November 2008 to January 2009, he was a member of the Obama-Biden presidential transition team. From 2009 to 2011, he was the principal deputy director of secretary of state Hillary Clinton’s policy planning staff. From 2011 to 2012, Chollet served in the White House Office as special assistant to the president and senior director for strategic planning on the United States National Security Council.
In addition to assisting Baker with his memoirs from 1996 to 1999, Chollet assisted former U.S. secretary of state Warren Christopher with the research and writing of his books In the Stream of History and Chances of a Lifetime. He also aided Richard Holbrooke in writing his book To End a War. In 2001, he assisted Strobe Talbott with his book The Russia Hand. Chollet is the author of The Long Game: How Obama Defied Washington and Redefined America's Role in the World (Public Affairs, 2016). He was a contributing editor to Foreign Policy, where he co-edited "Shadow Government," and he was also a regular contributor to Defense One.[12] He is also an advisor to Beacon Global Strategies and an Adjunct Senior Research Scholar at the Arnold A. Saltzman Institute of War and Peace Studies.
Chollet is the author, co-author or co-editor of six books on American foreign policy. His commentaries and reviews on U.S. foreign policy and politics have appeared in many other books and publications.
The Middle Way: How Three presidents Shaped America's Role in the World (Oxford University Press, 2021)
The Long Game: How Obama Defied Washington and Redefined America's Role in the World (Public Affairs, 2016)
The Road to the Dayton Accords: A Study of American Statecraft (Palgrave Macmillan, 2005)
America Between the Wars: From 11/9 to 9/11, co-authored with James Goldgeier (Public Affairs, 2008)
The Unquiet American: Richard Holbrooke in the World, co-edited with Samantha Power (Public Affairs, 2011).[18]
Chollet has contributed nearly two dozen op-eds to Defense One, a national-security publication based in Washington, D.C.