Between 2014 and 2016, California policymakers invested a half-billion dollars in the California Career Pathways Trust (CCPT). The initiative funded regional and local partnerships to establish career pathways designed to lead secondary school students to postsecondary degrees or certifications aligned with regional workforce needs. This brief suggests lessons that state policymakers can learn from CCPT about what it would take to increase the likelihood that cross-sector career pathways partnerships succeed and remain viable so they can make a sustained effort to both increase the number of skilled workers coming out of California's educational institutions and strengthen demand for those workers. The authors describe instances where regional efforts needed more state support to succeed and endure. They then recommend steps that state leaders could have, and still can, take to cultivate stronger regional collaboration to advance strategies that, like career pathways, depend on systemic changes across sectors to improve economic advancement for the state's citizens and communities.