The impact of psychological skills training (PST) package programs on life, health, well-being in general and South African youth in particular has been relatively neglected. For example, prior to this research the impact of PST on the core health component of psychological well-being had not been evaluated, nor had the conceptual and/or empirical relationship between psychological skills and psychological well-being been investigated. While PST is often conducted individually due to its personal and specific nature, group training should not be overlooked especially in South Africa where community interventions are an important part of health promotion. With the above considerations in mind a triangulated design involving individual, group and community interventions, as well as elite and expert case studies was utilized to evaluate the effectiveness of a PST program and to investigate the relationship between psychological skills and psychological well-being. Results based on quantitative and qualitative outcome and process measurements indicated general improvement in psychological skills, psychological well-being and sporting performance. Psychological skills and psychological well-being were found to be interrelated concepts, with overlapping components. Recommendations for ongoing and future research at individual, group and community level are made.