College enrollment rates have been on the decline over the past years, with more high school graduates choosing alternative pathways such as getting employed in an entry level job, pursuing a technical or trade training program, starting a small business, and entrepreneurship. This phenomenon may have been exacerbated by major events such as The Great Recession and the COVID-19 pandemic, as well as shifts in society's perceptions of the value of college degrees in today's economy. This may lead to creating challenges in the job market as the number of workers holding college qualifications may be affected. We conducted an investigation where we interviewed higher education administrators that are responsible for managing enrollment at five different Midwestern universities. The professionals included directors and associate directors of enrollment, provosts and vice provosts overseeing enrollment, as well as deans and vice presidents. The primary goal of the investigation was to discover the methods these institutions have been using to deal with the declining enrollment rates, which methods worked most, and which ones worked least, and what needs to be done to improve or create new methods to tackle this problem. The investigation concluded that factors such as the declining birth rates, declining high school graduation rates, the increased access and popularity of online learning, economic impact of recessions and the rising cost of education, as well as the impact of the COVID-19 pandemic, are some of the main reasons for the decline in college enrollment cited by the higher education administrators interviewed. To tackle this decline, some of the techniques employed by the investigated institutions include dropping the requirements for standardized testing, increasing scholarships, improving outreach to prospective students in high schools as well as strengthening advanced placement classes programs, and increased emphasis on transfer students to boost enrollment. In conclusion, we recommend that higher education institutions focus on boosting their scholarships and financial aid as much as possible, enhancing and investing in new extracurricular activity facilities and programs, promoting a culture of social support, and enhance cooperation with the market industries to improve and update the courses offered to better fulfill the market needs. [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.]