Simon's career in planning commenced in 1978 in the development control section with Sheffield City Council, where he worked until 1990. During that time he worked his way up to the level of a senior planning officer. The majority of his time in Sheffield was taken up with dealing with development control planning matters in the outlying western and northern areas of Sheffield, including large rural areas a substantial part of which is located within the Peak District National Park.

In 1990 Simon moved to a post as a principle planning officer with Barnsley Metropolitan Borough Council where he gained further experience in dealing with major projects throughout the Borough and in a full range of local planning authority procedures, including dealing with written representation appeals, Public Inquiries, enforcement matters and numerous 'run of the mill' planning applications. He left local government planning to set up his own planning and development consultancy in 1998.

Since 1998 his geographical area of work has been concentrated mainly in South and West Yorkshire, Lincolnshire and Derbyshire and has involved a full range of planning and development related matters, planning enforcement problems and the submission of planning and Enforcement Notice appeals. This work has involved a full range of large and small developments in inner city areas, industrial areas and land and buildings in the green belt. Simon has also acted as an expert witness in planning related prosecutions.