The purpose of this research is to define significant explanatory factors behind gendered differences in career expectations. The data was collected through a survey that was administered to undergraduate and graduate students who are in the beginning stages of their career development. The questions in the survey focused on determining the expectations that college aged men and women have for their future careers on a subjective and objective basis. In addition, the questions were intended to determine gender differences in four explanatory factors including personality, core self-evaluations, work life values, and gender fatigue. Findings from the study coincide with previous research in that women indicated lower career expectations on a monetary and hierarchical basis in the short term and at the peak of their career. The difference in expectations were found to be significantly correlated with gender differences in extroversion levels, beta work values, and gender fatigue, all of which are internal influences that help to explain the current gap in career expectations, and thus the gap in men and women's eventual compensation and advancement. The findings from the study also help to show that different expectations are caused by differences in how people define success. Implications for these findings can be looked at from two different perspectives. For decades, feminist movements were the approach, and equality was the goal. Now that our society claims gender equality, we are at a standstill in progression, even though there are still clear gaps in compensation and leadership positions. This research can be helpful for not only universities advising future graduates, but also companies currently seeking future employees. Recommendations for future direction are based on the findings from the study and the responses of the individuals.