Self-esteem seems to play a significant role in one’s quality of life. A key factor positively influencing self-esteem is the possibility to freely choose one’s relationships. Japanese tend to report comparatively low self-esteem levels, what may be due to modesty considerations though too. The prevalent East Asian concept of ‘face’ reflects one’s evaluation of how the self is seen by others, while the concept of self-esteem represents the own notion of the self. This article did qualitatively investigate what current and emerging situations in Japan are that require (new) responses from Japanese to maintain their face and to positively cultivate self-esteem. The interviews conducted revealed that losing face seems to involve a shame creating publication of a person’s inadequacy to meet social expectations that are formally or informally agreed respectively ingrained in the culture. Participants expressed some difficulties even for Japanese to interpret what in a particular relationship would be considered common sense and what adequate communication styles are. Social status and seniority are increasing one’s face value. Such value can be lent to others in the form of shared reputation and trust. The concept of face, rather than about self-esteem, seems to be about the maintenance or increase of social relational value. In conclusion, the learning and application of well adaptive communication and coping styles are required to successfully manage mixed low and high contexts in changing private and workplace situations in Japan.