Women’s advancement in the corporate workplace has taken significant strides over the last century. Research demonstrates, however, that despite an increased presence of female employees in mid-management positions, executive positions continue to be male dominated. Women are underrepresented in areas of governance, directorship, and executive leadership. This seems to contradict the apparent momentum of the promotion of women. This paper will unveil some of the hidden barriers that stubbornly exist for women in business. It will review research that demonstrates why gender inequality is difficult to recognize, the systems that perpetuate it, the complexities of how society views it, and the ways women respond to it. By understanding the interplay between external and internal obstacles, women who wish to assume positions of leadership can more easily navigate the labyrinth of gender inequality, and their male colleagues can better recognize the ways that they can either remove barriers or encourage equality. There are corporate, social and economic benefits to allowing women to fairly advance to positions of power. Recognizing and removing barriers is vital to the strength of companies, social networks and jurisdictions.