In this article, the author discusses how the creation of enrollment management organizations separate from traditional student affairs and academic affairs divisions have caused negative impacts on student learning. A relatively new organizational structure that first appeared in the mid-1970s, enrollment management has its roots in tuition-dependent private colleges and universities. Over the years, enrollment management organizations have gradually based their recruitment processes on the financial capacity of students. The author believes that the financial ability of a student does not always translate into the ability to be successful at the college level. As passengers on the same ship, the author suggests that student affairs educators, faculty, and enrollment managers need to begin to take steps to create new sails that strike a healthy balance between financial goals and learning goals.