This article examines career transition challenges through the lens of Danish philosopher Søren Kierkegaard's concepts of being "lost in the finite" (trapped by familiar roles and external expectations) versus "lost in the infinite" (overwhelmed by too many possibilities). The piece describes how people often define themselves by their resumes and past experiences, creating self-limiting career paths, while simultaneously experiencing anxiety when contemplating change due to the "dizziness of freedom" that comes with multiple options. Drawing on psychologist Rollo May's work, the article suggests that anxiety can serve as a catalyst for personal growth and creative innovation when properly harnessed. The piece identifies problems with traditional career advice sources like social media and Google searches, which provide fragmented and biased information, and frames career decision-making as requiring collective intelligence and multidimensional understanding of experiences from diverse individuals who have navigated similar transitions.