In this article, we discuss the pros and cons of transdisciplinary research using the results of a research project on lawns carried out in Sweden from 2013 to 2016. We viewed lawns as a complex ecological and cultural phenomenon and searched for different sustainable lawn solutions in urban areas of Sweden. Constraints on the research included the time and effort required for team members to become familiar with the different research approaches, participate in regular meetings and agree on joint methodology. Later in the project, the integration, analysis and understanding of field data, theoretical sources and practical implementation approaches were also time-consuming obstacles. Thus, the initial and final phases of the project were extremely important and demanded a lot of time and effort. Especially challenging was the cross-use of different methodologies from natural and social sciences. Such ambitious multiscale and multitask projects dealing with living urban nature and people require at least five years to complete, rather than the three years typically suggested for classical research projects. The pros of the transdisciplinary approach was its ability to incorporate results of natural and social studies into landscape design, the ability to involve stakeholders in different project activities and to disseminate the research results in practice. This research revealed that lawns are a relatively recent phenomenon that is still expanding globally. The social study component showed that mowing and creating smooth, green lawn surfaces is important to stakeholders (lawn users, planners and managers). However, in Sweden, there is a tendency for local citizens to accept more biodiverse plant communities. Working closely with open-minded stakeholders led to the real implementation of lawn alternatives, which, in turn, increased media attention. The initial concept—that management was a central factor to the whole transdisciplinary project—was confirmed. The goal of this article is to share the unique experiences and lessons learned by researchers of conducting transdisciplinary research and to make such complex research more successful.