Evolutionary scheduling and combinatorial optimisation is an active research area and attracts the attentions of many researchers from computer science and operations research. Many advances have been made in this field and its scope in terms of techniques and applications has been continuously extended. In this position paper, we provide an overall picture of some key challenges in the field, discuss potential future research directions, and give our position in the field. We focus on three major issues that are encountered in practice, namely dynamic changes, multiple interdependent decisions, and multiple objectives. Our view is that the researchers should step out of our comfort zone to deal with messy and complicated issues in real-world applications.