This chapter explores the challenges for families and schools in channeling ambitions in more productive directions. Today’s adolescents confront a world of growing pressures, which are also increasing mental health challenges. Parents’ vicarious ambitions can compound the problems if they push children to focus too much on extrinsic markers of success at the expense of intrinsic motivations to learn and ethical values. Both schools and families should help students to develop persistence, resilience, a strong moral compass, and commitment to the common good. Opportunities for service learning, internships and mentorships can encourage constructive ambitions. So too, parents and colleges must better control the preoccupation with prestige that has hijacked admission processes and encouraged gaming the system. Educators should also modify admission criteria such as legacy, donor, and athletic preferences that advantage already advantaged applicants.