Intentional Self-Regulation (ISR) or, more broadly, goal-directed behavior, is an essential skill in promoting positive and adaptive healthy development across the life-span. The Selection-Optimization-Compensation (SOC) model of ISR has described positive development among children, adolescents, and adults. However, the current SOC measure does not quantify the lived experiences and interindividual differences resulting from experience, training, and organizational culture. Using data from a multi-cohort, multi-year study among Cadets at West Point, this dissertation employed concepts from the decision making and risk-taking literature to conceptualize and test a model that describes interindividual differences in ISR based on lived experiences within a leadership context where risk is a vital decision-making consideration. Data were analyzed using a latent growth curve model to assess the association between ISR and risk-taking propensity, and to test the ideas that lived experiences are associated with differences in the ISR developmental trajectory, and that this trajectory is associated with important institutional outcomes. The results of this analysis suggest that within this sample risk-taking propensity is positively associated with intentional self-regulation above and beyond the average intentional self-regulation growth curve. Results of this research are discussed in relation to optimizing Cadet development, improving our understanding of contextual factors that influence ISR, and the importance of ISR and risk-taking within the military leadership context.