Given the increasing downsizing, restructuring, flexibilisation, and increasingly turbulent environment enhancing managers’ happiness and creative performance is a challenge for organizations. A supportive work environment substantially determines managers’ performance and behavioral outcomes. However, research has indicated that there is a lack of research on the mechanism through which a supportive work environment influences both happiness and creative performance. To extend the current understanding of managers’ happiness and creative performance, this study examines the relationship between supportive work environment (organizational support, job support, and social support), cognitive style, psychological capital, creative performance, and happiness. The structural equation model was used to test the proposed hypothesis for a sample of 513 middle managers in Taiwan manufacturing, service, and finance sectors. Results show that organizational support and job support relates positively to both cognitive style and psychological capital. Social support has a positive impact only on psychological capital. Psychological capital has a positive effect on creative performance and happiness, whereas cognitive style has a positive effect on creative performance and negative effect on happiness. Results advance the understanding of how a supportive environment can play an active role in influencing both happiness and creative performance.