Through a case study of Company X, a retailer, this paper clarifies reasons why women do not want to become managers in companies promoting women’s active workplace participation. In recent years, Company X has set the target for increasing the proportion of women in managerial positions to 20% and is working to do so. Specifically, Company X is targeting single women in their thirties, and these women are promoted to managerial positions before giving birth and after raising children. In this case study, however, few single women chief at Company X are interested in becoming a manager. In “promotion of women’s participation” Company X expects to increase the number of “women in management who marry and raise children.” This contradicts the working style of the single woman chief, however. For one thing, Company X’s managers are transferred every one or two years, and they work long hours, day and night. At the same time, Company X is reducing the location-specific employee system chosen by many married women. These circumstances not only make it more difficult for a single woman chief to marry, but also for women who are raising children to continue working as regular employees-never mind taking demanding managerial positions. Company X’s “active participation of women” aligns with Japan’s policy of promoting women’s active workplace participation, that is, emphasizing “bearing and raising children” and “promotion of women to managerial positions.” Resolving contradictions in Company X requires fundamentally changing the government’s policy on women’s workplace participation. However, if companies try to overcome this problem at the corporate level, they should assume a variety of woman managers.