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Pursuing degree programs in universities, particularly for postgraduate degree programs, has its share of challenges and opportunities for students all over the globe. Africa, and Kenya in particular, are experiencing an explosion in the rise of higher education and enrollment in university education. But postgraduate studies in Kenya are marred with an undulating, spiraling, and seemingly hopelessly unending journey, whose completion presents some kind of accidental surprise and disbelief to the students in question. Funding and balancing the demands of studies, family, and work are just some of the challenges that put one’s motivation at stake, hence overstretching one’s resilience throughout the course of doctoral studies. It is out of such a scenario that the author shares the experiences that he underwent to achieve his PhD. He hopes that these shared experiences will help future doctoral students, particularly in developing countries like Kenya, and give them an informed perspective on what to expect.