Although the US is easily the most liberal nations on earth, even in the 21 st century, women still struggle to establish themselves its largely male dominated social-political landscape. Today, only 19 CEOs in the fortune 500 companies are female and despite having 70 female congressional representatives, the number is diminutive considering there are 535 seats. In most cases, women, despite being qualified for positions, both in the corporate and political world discover that they simply cannot rise above certain pay grades although there is no legal or professional reason for them not to (Jalalzai, 2013). The illusion, of seeing their career objective yet being unable to achieve it is commonly referred to as the “glass ceiling”. However, despite the existence of this very real, albeit hypothetically named barrier, there are women who have challenged the stereotypes and managed to crash through the ceiling, or at least cause very big cracks to appear on it. This paper will focus on three such women namely, Hillary Clinton, Nancy Pelosi and Condoleezza Rice in and attempt to discuss what common characters they share and how it has enabled them to rise above the ceiling. Boldness In the process of analyzing these women, care must however be taken to avoid lumping them into a single category, which is a common and counterproductive mistake that only serves to reinforce gender stereotypes. One must resist the temptation to view them as “iron” women who have been successful, only because they have taken a drastically unfeminine perspective in life since the implication of that would be that, women have to model men to become successful. However, one trait that the women mentioned above appear to share is the fact that they are unreservedly bold. In a social political setting that has largely been designed to accommodate masculine ideals, it is easy for women to find themselves conforming to societal expectations and playing a secondary role to men. Therefore, for them to stand up against men in their own turf they need to be incredibly bold and all these women have lived up to this standard in various capacities. In fact, there is little doubt that each of the women has had to take on huge odds to make it in their respective field and in addition to a lot of hard work and stamina, they have had to be extremely courageous (Palmer & Simon, 2008). Condoleezza Rice for instance held down the posts of national security advisor and secretary of state, during the Bush’s presidency. She was one of the most powerful Americans and her actions and their impacts reverberated throughout the world. Although Hillary Clinton is not as abrasive in her approach as Rice, her career and willingness to take huge political risks engender a rare boldness. She has strived to step from under the shadow of her still popular former president husband and is attempting to smash the ultimate glass ceiling in America’s politics since it is widely believed she will be running for president in 2016. Nancy Pelosi on the other hand describes herself as having shattered not the glass but marble ceiling in her election as the first female house speaker (Palmer & Simon, 2008). When one considers that, the house of representatives is dominated by men who occupy over 85% of the seats, her running for, speaker was very bold move as both a politician and woman. How they have demonstrated boldness Pelo