Tackling the societal challenges we are facing requires collaboration among many actors with quite different backgrounds and interests. Indeed, these challenges call for systemic and cross-sector collaboration. However, such collaboration is associated with several problems, concerning the creation and distribution of value among the actors involved. We need a new way of thinking about how value should be created and distributed among the involved actors to be able to make the necessary system-wide shifts that are needed. This article presents findings from an in-depth field study of the High-Capacity Transport (HCT) project and focuses on the system-wide shift towards more sustainable models within the transportation sector in Sweden. The article highlights four pressing challenges that may negatively influence collaboration, search, ideation, and value creation processes, and identifies four corresponding value pathways for effective system transformation projects. It offers advice on how to maneuver through these four challenges in system transformation projects to produce socially valuable outcomes.