Simon's early musical training from his father led to him becoming a chorister at Southwell Minster. Whilst there he studied organ with the cathedral organist Kenneth Beard. After studying at the Royal College of Music and London University he became Assistant Organist at Peterborough Cathedral where he made several recordings and live broadcasts on BBC Radio 3.

After leaving Peterborough, Simon became Director of Music at St Peter's in Brighton. In 1997 Simon was appointed Tutor of Academic Music and Staff Conductor at Chethams School of Music in Manchester. During this time he worked extensively as a freelance conductor, holding down the positions of Musical Director of the Gorton Philharmonic and King Edward Society Chorus and Orchestra as well as being Director of Orchestras at the King’s Youth Music Centre in Macclesfield. He was also Principal Conductor of Northern Baroque Orchestra and appeared as a Guest Conductor with Wilmslow Symphony Orchestra.

Simon was Director of Music at Bryanston School in Dorset from 2001 to 2002. He left to pursue his conducting career, and was appointed Associate Conductor of the Royal Oman Symphony Orchestra. After a hugely successful season he was invited to be the orchestra's Principal Guest Conductor for the following season. Simon became Musical Director of the London Gay Symphony Orchestra in 2005. He also currently conducts the Enfield Youth Symphony and Derbyshire County Intermediate Orchestras. Simon has performed as a conductor at the Barbican and Queen Elizabeth Hall in London and made his debut at London's Cadogan Hall in a performance of Verdi's Requiem.