In 2011, PayPal co-founder Peter Theil introduced the first Thiel Foundation Fellows--students who agreed to drop out of college to do scientific research, start a tech company, or work in a social movement. Although this may have been seen as a radical and daring idea at the time, 400 people applied for 24 scholarship awards of $100,000 apiece. Thiel believed this opportunity directly addressed two problems that existed in the traditional college-bound track; first, "a bubble in higher education" and, second, a dearth in Americans developing breakthrough technologies designed to address some of the country's most urgent challenges. Innovations such as Theil's have prompted higher education to respond to the growing concerns over the relevance of traditional higher education. Within the current discussion, disagreement has arisen, particularly between faculty and students, about how to address the existing problems. With the authors' personal concerns about student engagement, they began their own investigation into the precipitating barriers they observed among their first-year students. Their inquiry began to align with concerns being publicized from various vantage points in higher education--and to illuminate "student disengagement" as a far more widespread issue. Herein, the authors discuss the perspectives from both the side of the faculty and the side of the students and offer steps to reaching a common ground between the two.