Research indicates many women prefer being self-employed and entrepreneurs, creating value based on their personal beliefs, rather than sitting on boards as “Ornamental Directors”. Furthermore, the road to corporate boards for women has been long, tortuous, and bumpy, but needlessly so. Several theoretical explanations have been suggested for this situation, often with overlap and similarities. However, we believe that in other barriers are due to poor ‘signaling’ of success for female directors and structural issues. The messaging comes in the form of networks and nomination process bias, role model and mentor shortages, work–family balance, legal ambiguity, policies, and cognitive behavior. This leads to what we call the “Ornamental Director” syndrome.