Many job seekers in higher education are unaware of how large a discrepancy there can be in terms of financial potential for mathematics education jobs in higher education. Recent research on this topic has focused on the base salary (Reys, Reys, & Estapa, 2013), but other financial factors have been left unstudied. Through two cases, the researcher demonstrates a large gap that exists in net pay when major financial factors beyond base salary are considered, specifically insurance and retirement benefits. This article will spur conversations among faculty and graduate students in mathematics education doctoral programs allowing mentors to draw from their own experiences when mentoring others in the search for a first or second job.