Simon gained a BA in Psychology from the University of Sheffield in 1990, going on to complete a PhD in Developmental Psychology in 1994, looking at the question ‘Can blind and visually impaired children use tactile maps?’. Following this, he gained funding for three years from the ESRC to continue research focused on the design of tactile maps and graphics. He became a Lecturer in Developmental and Environmental Psychology in 1996, starting his lecturing career at Glasgow Caledonian University, before moving to London Guildhall University and then to the University of Surrey. He continued to develop his interest in spatial cognition, navigation and tactile maps/graphics for blind and visually impaired people, jointly running a six-year EPSRC funded interdisciplinary project with physicists, materials engineers and geographers focused on improving the design of tactile graphics. He was a consultant for the BBC 2 series "Tales from the Map Room" and contributed an interview to the programme on the use of tactile maps for children.

Having felt an increasing desire to apply psychology more directly in the community, in 2007 Simon trained as an Educational Psychologist (EP) at the Tavistock and Portman Clinic, gaining his professional Doctorate in Child, Family and Community Psychology in 2010. He has worked as an EP in the London Borough of Wandsworth since that time. In addition to schools based work, he spends one day a week in the Wandsworth CAMHS service. He was a Fieldwork Tutor for the UEL EP doctoral programme from 2013 to 2017 and has subsequently been an Academic and Professional Tutor on the UCL EP doctoral programme.

Simon has maintained his interest in blindness and visual impairment, being an active participant in the PsyVIC group and workshops run by the Mary Kitzinger Trust. In 2014, he was commissioned by the RNIB to produce guides for adjustments and alternatives to the 11+ Tests, which were published by GL Assessment. He is a member of the editorial board of the British Journal of Visual Impairment and of the British Standards Institute (BSI) Tactile Information Coordination Group.