Positive Youth Development (PYD) programmes are often conceptualized and led by adults with little or no youth input. The purpose of this study was to better understand youth definitions of success, obstacles they face in achieving success, and how they perceive others can help. Interviews were conducted with 24 youth from three different contexts (swim club, church group, and reform home) in Trinidad and Tobago. The results indicated that youth have a varied understanding of success. Further, many youths’ definitions mirror those prescribed in PYD literature. Youth identified a variety of obstacles in their quest for success, and though similarities existed, several obstacles were context dependent. Finally, youth identified support and assistance as the best mechanisms to propel them to success. Support, both informal and formal, points to the significant role non-parent adults serve in the lives of youth. Implications for youth programmes and future research are discussed.