The need to pursue higher degrees to meet job demands, while at the same time working for social obligations, can be quite challenging. This is especially so when such students have to pay their tuition privately. This paper is based on the findings of a study done among students on masters programs in higher education at Makerere University in 2008. It reports some of the challenges graduate students face as they struggle to attain higher degree qualifications needed in order to secure better jobs, gain promotion, or to
retain their jobs at their current places of work. Specifically, it reports some of the risks students take while looking for additional funds to pay university fees; while at the same time sustaining families and other social economic obligations. A lot of study time is lost in various activities students engage in to realize the needed funds, a fact that could have adverse effects on the quality of their study performance.