Brad Sloan, a middle-aged man, grapples with feelings of inadequacy as he navigates his midlife crisis. He appears to have a comfortable life with a stable job and a loving family, yet he can't help but compare himself to his more successful college friends. As he prepares to take his teenage son, Troy, on a tour of potential colleges, Brad is haunted by thoughts of missed opportunities and the accomplishments of his peers. These comparisons lead him to a downward spiral of envy and self-doubt, deeply affecting his sense of worth and happiness.

During the trip, Brad's reflections on his life choices intensify, causing tension between him and Troy. He begins to realize how his preoccupation with status has clouded his judgment and understanding of what truly matters. Throughout this journey, both literal and metaphorical, Brad seeks to reconcile his feelings of discontent with the reality of his life. The various encounters and experiences during the college tours force Brad to confront his insecurities and ultimately find a path toward self-acceptance.