Brad Sloan leads a seemingly fulfilling life as the head of his own non-profit organization, spending quality time with his caring wife, Melanie, and their son, Troy. However, beneath the surface, he grapples with feelings of inadequacy as he compares himself to his more successful friends: Craig Fisher, who works in the White House and is the author of a best-selling book; Jason Hatfield, who has achieved great success in hedge funds; Billy Wearslter, a retiree enjoying the sun in Maui after selling his company; and Nick Pascale, a Hollywood director.
As Brad prepares for a trip to Boston with Troy to explore colleges, his son reveals his ambition to attend Harvard, sparking in Brad a desire to reclaim his own lost aspirations. However, their plans hit a snag when they arrive a day late for their admissions appointment. Although Brad initially tries to advocate for them to meet the admissions committee, it's ultimately Troy who helps him back down. In another moment of reluctance, Brad reaches out to Craig for assistance, further highlighting his feelings of inadequacy. He discovers troubling news about Nick's life—he married his boyfriend without inviting Brad, reinforcing Brad's insecurities about his own perceived failures.
Throughout their trip, Brad reflects on his dwindling intimacy with Melanie, pondering if her contentment has inadvertently stifled his drive. During a conversation with Troy, he admits to feeling sidelined in life, prompting his son to notice his distress. A conversation with Craig ultimately leads to a meeting for Troy with a renowned Harvard music professor, only further complicating Brad's feelings of envy.
In a twist, they meet Ananya, a talented musician and friend of Troy, along with her acquaintance, Maya. Brad finds Ananya’s enthusiasm refreshing and reminiscent of his own youth, but is confronted by her candid critique of Craig's arrogance, deepening his contemplations about success and failure. After sharing a meal, Brad spends an evening with Ananya, revealing his regrets about choosing a non-profit career over financial prosperity. Despite her admiration fading, Ananya’s insightful perspective reminds him of the privileges he enjoys compared to others.
Troy has a pivotal moment when he meets his music idol, yet their perspective clash leads to a heated disagreement between father and son. The situation becomes serious when Jason calls with distressing news regarding his daughter’s health, leaving Brad shaken and preoccupied. Ultimately, as they visit Tufts, old memories resurface with the unfortunate news of the passing of one of Brad's professors, blending nostalgia with sorrow.
As the story unfolds, a dinner meeting with Craig opens Brad's eyes to the struggles hidden beneath his friends' successful façades—Jason’s legal troubles, Billy’s addiction, and Craig's untoward comments regarding Nick. When their conversation turns sour, Brad leaves, seeking solace with Troy at an orchestral performance featuring Ananya and Maya. The music stirs deep emotions within him, allowing him to reconnect with his passions.
Later that night, during a candid exchange, Troy reassures Brad of his worth, explaining that people's perceptions are often self-centered. Troy emphasizes that his dad's opinion matters most to him, which fills Brad with a sense of comfort. In a moment of introspection, Brad envisions his future and concludes the film with the hopeful mantra, > "We're still alive. I am still alive," as he relaxes into sleep, his imagination wandering to visions of Troy busking on the streets.
