This chapter presents a discussion about similarities and differences between working with mathematical modelling in ‘school’ and mathematical modelling as a ‘professional task’ in the workplace based on empirical and theoretical research studies. Issues discussed concern goals; technology; division of labour, communication and collaboration; model construction, including the application and adaption of pre-defined models; projects; and risks involved in using the models. Based on this discussion and examples from innovative teaching practices, approaches to simulate modelling as a ‘professional activity’ in educational settings are explored and exemplified with a role play activity.