I recently dialogued with a few colleagues about the Chronicle of Higher Education Op-Ed piece, Higher Ed Is a Land of Dead-End Jobs. So, episode 2 was a timely conversation unpeeling the ill-discussed realities of working in higher education - the undefined ladder to leadership, the role of mentorship, and the impacts of race, gender, and a lack of representation. It was refreshing to hear the divergent paths of three unique leaders, although each sit within the S.E.M. area of Records and Academic Services. Although I loved A Different World, I never imagined I could, or would, work in higher education. Listening to the conversation led me reflectively down my career path and various personal experiences that span two decades.