Simon trained at the Northern School of Contemporary Dance in Leeds, before touring with their student company, Verve. He went on to develop an interest in physical theatre and object manipulation, performing with Tilted Productions in Glacier, Trapped, Masquerade and Seasaw. Moving into puppetry, Simon worked extensively with Theatre-Rites on their productions Paradise, Mojo, Bank on It and Rubbish. Other theatre includes The Drowned Man: A Hollywood Fable for Punchdrunk, Benvenuto Cellini for English National Opera/Terry Gilliam, Mucky Pup for Theatre Alibi, Time for Tea for Wet Picnic, The Weirdy Beardies, The Nerdy Birdies and The Librarians for Pestiferous Theatre.