Management of “wicked problems”, messy real-world problems that defy resolution, requires thinkers who can transcend disciplinary boundaries, work collaboratively, and handle complexity and obstacles. This paper explores how educators can train undergraduates in these skills through applied community-based research, using the example of an interdisciplinary research program at Clark University in Worcester, Massachusetts, USA. Participating students strengthened their abilities to handle setbacks in the research process, improved communication and teamwork skills, and gained familiarity with interdisciplinary investigation. Programmatic elements that could transfer well to other settings include studying local human–environment problems, working in multigenerational, small groups, and using multiple methodologies.