Women’s roles in society have changed significantly throughout the years. The movement to support the rights of women has been ongoing throughout the evolution of society but has been especially prevalent in the last century. The 1960s are when women began to enter the workforce instead of being limited to presuming roles as homemakers. Since that point in time, women have continued to thrive in the workforce and have pursued a larger variety of positions in various fields. Even though the opportunities for women continue to grow, there still seems to be an underrepresentation of women in science, technology, engineering, and mathematics (STEM) related fields. The underrepresentation of women pursuing physician and entrepreneurship roles in STEM will be analyzed and the challenges this group of people specifically encounter will be examined. Our first proposal to encourage women to enter STEM focuses on middle-school initiatives and incubator programs. The second proposal, based on commonalities females face within the workforce, is finding a better work/home life balance with the development of new maternity/paternity leave policies. Through these initiatives, we believe that the gender gap in STEM can be bridged.