Simon gained early experience of classical music through the Westpac Secondary Schools Chamber Music contest and the National Youth Orchestra, which he led in 1978–9. On leaving school he joined the NZBC Schola Musica for a year, before attending Otago University to study for a BA/BMus, completing the latter at Victoria University. During this time he worked in several regional orchestras.
Subsequently, he spent five years in Australia, undertaking postgraduate study under Jan Sedivka, and freelance work in Brisbane and Hobart with various orchestras, before joining the NZSO in 1986. Simon was a member of the NZ Chamber Orchestra for several years. In 2000–2001 after receiving the Montana Study Award, he spent 12 months on leave in London, having private lessons and completing a course in community music education at the Guildhall School of Music and Drama. His violin is a Giulio Degani, which, along with his house, turned 100 in 2008!
Simon is a keen sailor and also likes to keep fit by cycling and swimming.