The purpose of this study is to investigate the relationship between activation of middle-aged and older white-collar workers and that of the organization itself. Previous studies have shown that the factors of activation of middle-aged and older white-collar workers were promoting psychosocial development (generativity) in middle adulthood and in being a self-directed person. This study aims to investigate the effects of those factors on the activation of the organization based on the I-I chart (Takahashi, 1993), a measurement of the organizational activation. We conducted a questionnaire survey with white-collar workers in conjunction with general incorporated foundation “P” to research and educate on sales activity. The participants were 291 workers who were employed by companies (Number of surveys distributed: 291; Number of surveys collected: 265; Collection rate: 91%). The major findings were as follows: (1) Promotion of self-directedness and development of generativity affected activation of middle-aged and older white-collar workers and of the organization. (2) A moderate effect of self-directedness was found on the impact of activation; development of generativity of a highly self-directed person has a high possibility of increasing his/her activation. However, developing generativity in a person with low self-directedness may diminish activation.