Modelling languages and frameworks have been the key technology for advancing Model-Driven Engineering (MDE) methods and tools. Many industrial and research tools have been realised and are used across many domains. Hence, we think it is the right time to define what should be the future of modelling technologies, especially the requirements for the next generation of modelling frameworks and languages. In January 2020, the Second Winter Modelling Meeting (WMM2020) was held in San Vigilio di Marebbe (Italy), focusing on the analysis of the state of research, state of practice, and state of the art in MDE. The event brought together experts from industry, academia, and the open-source community to assess (i) what had changed in research on modelling in the last ten years, (ii) which problems are still unsolved, and (iii) which new challenges have arisen. This article presents a set of success stories and driving success factors of modelling and MDE, as well as a set of challenges and corresponding research directions that emerged from the synthesis of the results of our analysis.