Freedom is like the morning; some sleep and wait for it to come, but others stay awake and walk all night to reach it. This chapter focuses on the many challenging roads that graduate students of color are likely to encounter when pursuing and maintaining an academic faculty position. Applying for academic positions can be a lengthy and scary task. For professionals looking for academic positions, location, salary, tenure track, and prestige may be important factors considered in the decision making process. The chapter helps to stimulate one's own critical thinking and decision making as they think about beginning a career in academia. It also provides a list of questions to help you reflect on academia as a possible career option. To pursue a career in academia and to find whether the professoriate is the right niche, it is helpful to consider some important questions before dedicating time, energy, and resources to the application process.