Milbrey McLauglin, the David Jacks Professor of Education and Public Policy at Stanford University, Emerita, spoke to an emeriti/ae audience on April 22, 2021. She traced her life trajectory through college and an “awakening” of sorts in Kansas City, Kansas, to policy analysis at the RAND Corporation focused on disadvantaged youth, and quite “unintentionally” to a faculty position at Stanford where she was the founding director of the John W. Gardner Center for Youth and Their Communities. Professor McLaughlin discussed several themes in her work helping to identify policies that can improve outcomes for vulnerable urban youth, including “mutual adaptation” by local educators and careful attention to the settings and contexts of both teachers and students. She highlighted the power of well-designed opportunities such as the CYCLE program in Chicago, that allowed youth to overcome hostile conditions in Chicago’s Cabrini-Green public housing project and embark on positive life paths.