Over the years, the gender wage gap has received substantial attention by social scientists and generated a plethora of international research. Recently, however, this issue has been brought into the limelight again with new and often provocative findings, confirming that inequalities and discrimination against women still pertain in the workplace. This chapter sheds light on the overall trends noticed both at the European and international levels, whilst taking into consideration gender differences in relation to educational attainment, occupational type, and the manifestation of various work contracts, often to the detriment of female success in the job. It is suggested that these trends should not be occurring today, given the fact that advancements in terms of ensuring equality and modernization are at the top of most organizations’ and governments’ agendas. Furthermore, it is advocated that women’s success in leadership positions may indeed be possible, although it often comes with a price tag in terms of psychosomatic health, poorer job and life satisfaction, as well as hindering the family in well-being and overall sustainability.