Career readiness programming is designed to help young people gain awareness of self, knowledge of the requirements for work, and the skills to reason for oneself to make career choices for their future. Although efforts to help people identify with careers have been traced back to the fifteenth century, the responsibilities for career guidance and career readiness for adolescents are an ongoing debate between educators and policymakers. The assumptions about career readiness are that the responsibility lies in the hands of secondary education institutions and that young people are appropriately guided, making them career ready. However, factors such as accountability, curriculum constraints, and the skills gap contribute to young people’s ongoing challenges in bridging school to work, leaving them vulnerable and unemployed. In this inquiry, the research investigated assumptions, biases, expectations, and multiple perspectives within the community of expatriate students impacted by the quality of or lack of career education in secondary schools in the United Arab Emirates. A literature review approach in the form of an interpretive paradigm, the investigation focused on the connections between career guidance and career readiness for secondary students. The findings contributed to the limited research on the topic of career readiness for secondary students.