Does the expansion of the digital economy generate more remote working? Some think that is the case since working from home reduces carbon emission and energy consumption. People are now confronted with a connected environment through digital technologies that change how they live, behave, and work. In this context, the purpose of this paper is to establish the importance of authenticity in relation to two scenarios, respectively working from home or in the office. Authenticity is a tripartite concept defined by (1) authentic living, (2) self-alienation, and (3) accepting external influence. The focus of the study is on the third dimension of authenticity—accepting external influence. Additionally, stress in the workplace is also studied, as it plays an important part for authenticity. Gender is also considered when analyzing external influence and stress in the workplace, as women and men may perceive external influence and stress differently. A total of 258, among which 68% were women and 51% worked in the private sector, responded to a self-reported questionnaire. A paired t-test showed that participants had a moderately low level of accepting external influence and work-stress when working from-home, compared to the office. Furthermore, for women, there was a significant difference in accepting external influence when working from the office than when working from home. However, the place of work did not affect the perceived stress for this group. In the case of men, there was no significant difference between work environments in regard to neither accepting external influence nor stress. A Pearson’s correlation test suggested a moderately positive correlation between work-stress and accepting external influence, in both scenarios (from home and from the office).