This paper discusses the importance of incorporating personal assistance into interventions aimed at improving long-term education and labor market success. While existing research demonstrates the cost-effectiveness of low-touch behavioral nudges, this paper argues that the dynamic nature of human capital accumulation requires sustained habits over time. To foster better habits, social connections are critical for encouraging enduring effort and intrinsic motivation. The paper showcases examples from various stages of human capital accumulation, including early childhood, adolescence, and adulthood, in which interventions that incorporate personal assistance substantially out-perform less intensive nudges. We underscore the importance of interactive support, guidance, and motivation in facilitating significant progress and explore the challenges associated with implementing cost-effective policies to provide such assistance.