After Graduating from Bristol University, Simon spent three years in stage management before directing his first productions. He wrote and directed Double Act at the Leicester Haymarket Studio and Captain Incredible at the Leicester Phoenix Arts Centre before going to the Bolton Octagon as Young People's Director. At the Octagon he directed several youth theatre productions including The Tempest and his own play Love In A Field Of Poppies, which later went on to win the Joshua Tetley Award. He also directed the premier of John Chamber's play Yoiks, Oiks!!

Simon wrote and directed Rock-Me-Amadeus - a play about Mozart which toured nationally for Compass Theatre; and Now We Are Engaged for the national Museum of Photography, Film and Television. He also wrote Fairplay, commissioned by Southport Arts Centre and broadcast by BBC Radio Four in 1995. In 1993 he took over as director of The Angles Theatre and Arts Centre, and whilst there he directed productions of A Midsummer Nights Dream, An Evening With Gary Lineker and his own adaptation of The Snow Queen.

Simon joined Hull Truck Theatre in September 1995, where he has directed Alan Ayckbourn's Relatively Speaking, The Twelve Days of Christmas by world famous children's TV author John Cunliffe, John Godber's Hooray For Hollywood, Mick Martin's A Weekend In England, David Bown's Stand, Shakespeare's Macbeth and Alan Bennett's Talking Heads. He also directed Kissing Sid James by Robert Farquhar which played at Hull Truck Theatre in February 1999 before embarking on a nation-wide tour of Great Britain. He wrote and directed Gold!, an 80's musical, for Hull Truck Theatre which also toured nationally through Autumn 1999.

In 1999 he became Executive Director of the Octagon Theatre in Bolton.  Here he directed Misconceptions by David Lewis which will was nominated for Best Production in the Manchester News Theatre Awards 2001, and 100 years in Worktown, a Year of the Artist funded projected which produced a piece of theatre from an oral history project examining working life in Bolton over the last century.

He worked for two years in Television, both for the BBC and on ITV's "Coronation Street" as the programme's Script Editor.

In April 2005 Simon joined the Gala Theatre in Durham as Director. Over the last three years he has worked with a new team at Gala to make the venue one of the most successful in the North East. The Gala now presents more films and performances each year and audiences continue to grow.

One of the most important strands of his work in Durham are the in-house professional productions - Simon has directed all seven of these to date and is working on some exciting, high profile projects for the future. He has also recently collaborated with Rodney Bewes on a new play about Jerome K. Jerome which is currently on a national tour. Later this year he will be writing and directing the Gala's first in-house pantomime, Aladdin.