Navigating the roles and responsibilities of graduate work is a complex, and often confusing business of workflows, labor (emotional and physical), and moving in several different directions. As graduate students, we find solace and compassion in the words and (mostly) shared experiences of our colleagues, and challenges in the desires, requirements, and “this is your life now” statements of our supervisors and faculty mentors. To be a trainee in the academic context of leisure studies is to make an already complex work of personal development and intellectual labor even more complicated. Building on personal experience and the collective experiences of my colleagues, this paper will discuss PhD student experiences in leisure, and the deep influences that structural and social changes are having on those same students. It will explore our perceptions of post-PhD horizons, the challenges of student lives, and the complexities of being both a professional and a novice at the same time. As graduate students, we navigate these issues using the tools at our disposal (both traditional and modern), all-the-while wondering if we are doing any of it the “right” way. Enlisting the attractive metaphorical spaces of sailing and the crew of a tall ship, this paper explores the academic seas as a trainee on the SS Academe.