The exploration of the skill acquisition process has been a central topic in the sport literature. Research examining athletes’ developmental pathways in sport have advanced our understanding of skill acquisition in sport and the social and contextual factors that underlie this process (Bridge & Toms, 2013; Côté, Erickson, & Abernethy, 2013; Ford & Williams, 2017). The purpose of this chapter is to review the concepts of early specialization, early sampling, and early engagement (e.g., Côté, 1999; Ericsson, Krampe, & Tesch-Römer, 1993; Ford, Ward, Hodges, & Williams, 2009) and to discuss how these concepts can influence athletes’ skill acquisition and development. The role of motivational processes, such as interest, in facilitating skill acquisition and athlete development is also discussed. Finally, this chapter presents practical implications for sport stakeholders and offers directions for future research that may lend new insight into how skill acquisition, and the long-term outcomes of sport participation, can be fostered.