[8] Rifkind began his career in journalism as an editorial assistant for the show business website Peoplenews.com, before becoming a freelance writer for The Times and the Evening Standard, and a columnist for The Herald in Glasgow from 2002 to 2005.

In The Times, Rifkind writes a Thursday opinion column, and a Saturday satirical diary ("My Week") in the style of a public figure in the news.

From 2007 to 2017 he wrote a fortnightly column for The Spectator, striking a liberal, pro-European tone which ran against the magazine's conservative, Eurosceptic editorial line.

[10] Throughout the general election of 2015, he presented Campaign Sidebar, a Saturday morning political review show on BBC Radio 4.

[15] In August 2014, Rifkind was one of 200 public figures who were signatories to a letter to The Guardian expressing their hope that Scotland would vote to remain part of the United Kingdom in September's referendum on that issue.

[16] In a 2011 Times column, Rifkind admitted that on 23 November 2010 he had inserted fictitious information about Queen Victoria in Wikipedia's article on the date 29 April.