A woman’s self-esteem, defined as “a realistic respect for or favorable impression of oneself,” can have a profound impact on her overall life choices and outlook. Low self-esteem is associated with numerous consequences such as eating disorders, alcohol abuse, sexual promiscuity, and social withdrawal. This study investigated the self-esteem level of college-aged women as compared to that of women at midlife and also identified the external factors that impacted this perception of self-esteem. It was hypothesized that the intense focus on women’s rights and political activism of the 1960’s and 1970’s would have promoted greater self-esteem in young women of that era, as compared to the largely apathetic culture of present-day young women. A qualitative and quantitative study was distributed to 29 college-aged women and 22 middle-aged women who were asked to reflect on their current self-esteem levels. The women at midlife were also asked to discuss their perceived self-esteem when they were college-aged. In general, college-aged women reported inconsistent levels of self-esteem, many reporting that it depended on numerous external factors such as relationships, academic success, family situations, appearance, and the media. Almost universally, the women at midlife reported that many of these same factors also influenced their self-esteem, but that they have become much more self-confident with maturity and age. However, few women at midlife reported feeling more self-esteem during their college years due to the political activity of the times. School and medical social workers need to be aware of the emotional and physical consequences associated with low or unstable self-esteem in college-aged women in counseling and health agencies.