Simon graduated with a Masters in Vocal Performance supported by the Carne Trust at the Royal College of Music. Simon has performed with a number of opera companies, such as Opera Australia, Grange Park Opera, English Touring Opera, Wexford Festival Opera, Scottish Opera and Sydney Chamber Opera. With these companies he performed and covered roles, such as Peter Quint (Turn of the Screw), Belmonte (Die Entführung aus dem Serail), Fenton (Merry Wives of Windsor), Don Ottavio (Don Giovanni), Borsa (Rigoletto), Trin (Fanciulla del West), Grimoaldo (Rodelinda), Bajazet (Tamerlano), Arnalta (L’incoronazione di Poppea), Parpignol (La Boheme) and Monsieur Triquet (Eugene Onegin).