Dear graduated from Coventry Polytechnic before completing a diploma in journalism at University College Cardiff. From 1989, he worked for the Essex Chronicle and the Big Issue, joining the National Union of Journalists (NUJ).[1] He led an eleven-month strike at the Chronicle against de-recognition of the NUJ.[2] Between 1994 and 1997, he was the editor of the Big Issue in the Midlands, then in 1997 became the National Organiser of the NUJ.[1]
In 2001, Dear was elected as the General Secretary of the NUJ,[1] its youngest ever leader, and only the second to serve two terms.[2] He also spent time as a member of the General Council of the Trades Union Congress.