He took the Westminster Press diploma in journalism, starting with the pre-entry course at Hastings in autumn 1992 while a trainee reporter with the Brighton Argus, and moved to the Financial Times and thereafter Newsweek.
Wolffe covered the entire length of Barack Obama's 2008 presidential campaign for Newsweek magazine, traveling with the candidate and his inner circle from his announcement through election day, 21 months later.
Before Newsweek, Wolffe was a senior journalist at the Financial Times, serving as its deputy bureau chief and US diplomatic correspondent in Washington.
In April 2009, he joined Public Strategies, Inc. — a corporate-strategies firm run by Dan Bartlett, former director of White House communications under George W. Bush[5] — as senior strategist.
Olbermann wrote at Daily Kos that "the broadcast network's very tough practices exec vetted this other job (and as indicated, the work he's done for us), found no interrelation."
On the edition of 29 January 2013 of The Last Word with Lawrence O'Donnell, Wolffe mentioned that he had recently become a naturalised US citizen, although he did not give a specific date.