This study investigated the relationships between context-based assets (personal, family, school, social, and community) and gratification delay, hedonic well-being, and psychological well-being. The study participants were 614 students selected from private, public rural, and public urban secondary schools. Data were collected using selected items from scales related to gratification delay, life satisfaction, positive and negative affect, psychological well-being, and developmental assets. The data were analysed using canonical correlation and two-way between-groups ANOVA. The results revealed a statistically significant relationship between context-based assets and gratification delay. In addition, context-based assets were also significantly correlated with the hedonic well-being and psychological well-being variables. The commonality coefficient showed that personal assets made a great contribution to the canonical solution of all the functions. The results further indicated that experience with assets differs as a function of school type, but gender did not have a significant effect. It is concluded that context-based assets are highly associated with positive youth development outcomes, including the ability to delay gratification and enhance hedonic and psychological well-being. Research with an experimental design should be conducted to further investigate and understand how intervention on each context-based asset contributes to youth thriving.