This study examined the experiences of undergraduate student leaders at a small, private institution of higher education in the New England region and specifically how those undergraduate students made sense of their experiences as student leaders and the impact that had on their career readiness based on the competencies identified by the National Association of Colleges and Employers (NACE). Alexander Astin's Student Involvement Theory (1984) was used as the theoretical framework for this study. Semi-structured interviews were conducted with eight third- and fourth-year students. The transcripts were carefully analyzed using Interpretive Phenomenological Analysis (IPA). Three findings emerged from the analysis: 1) the costs associated with attending college impacted the participants decision and motivation to get involved with clubs and organizations, 2) the participants involvement as student leaders allowed them to develop skills and have experiences that they claim they would not have received in the formal classroom environment, and 3) the COVID-19 pandemic impacted their involvement experience and helped prepare them for the workplace. These findings were examined in the context of Astin's (1984) theory and are affirmed within existing literature. Recommendations for practice are shared and suggest that colleges and universities look to incorporate the benefit of soft skill development in their practices across campus, from marketing to the use of cocurricular transcripts. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]