This chapter explores major issues encountered by many of the 1.5 million baccalaureate recipients each year (National Center for Educational Statistics 2006) who enter the workforce with inappropriate expectations, attitudes, job experiences, and levels of preparedness. Transition from college to a first full-time job is an exciting and much anticipated event, but it creates distress as well as eustress. Unlike the transition from high school to college, entry to the workplace represents a relatively clear demarcation from the past in one's identity, sense of responsibility, independence, intellectual activities, relationships, and life-style. Consequently, this transition is also a period of incredible uncertainties and insecurity. After introducing the topic with four contrasting approaches to reporting on transition stress, I summarize models of transition and psychosocial and cognitive development that serve as a framework for understanding organizational and related factors that contribute to stress. I conclude with recommendations for increasing workplace readiness.