In this slyly clever comedy, a struggling entrepreneur named Dave launches a peculiar startup called "Hindsight Services," offering clients the ability to purchase detailed, post-event analysis of their past mistakes. As played by Jason Sudeikis, Dave is a fast-talking optimist who believes he has found the perfect solution for everyone from jilted lovers to failed investors, all desperate to understand where things went wrong. His small but dedicated team, including a skeptical data analyst portrayed by Rashida Jones and a tech wizard played by John Malkovich, must navigate a growing roster of eccentric clients whose requests range from the heartbreakingly mundane to the absurdly catastrophic. The central conflict arises when Dave must decide whether his service truly helps people move forward or simply traps them in an endless loop of regret. Bursting with sharp dialogue and witty observations about modern self-help culture, the film balances its laugh-out-loud moments with a surprisingly warm meditation on acceptance and the value of looking ahead rather than back.