Ryan Bingham (George Clooney) makes his living traveling to workplaces around the United States and conducting layoffs for bosses too cowardly to do it themselves. Ryan also delivers motivational speeches, using the analogy "What's In Your Backpack?" to extol the virtues of a life free of relationships with people and things. Ryan relishes the comfort of anonymity during his perpetual travels. His personal goal for his life is to achieve ten million frequent flyer miles with American Airlines. While traveling, he meets another frequent flyer named Alex (Vera Farmiga) and they begin a casual relationship. Ryan is called back to his company's offices in Omaha, Nebraska, where he finds out that an ambitious, freshly-graduated, young coworker, Natalie Keener (Anna Kendrick), is promoting a plan to cut costs by having employees stay grounded and conduct layoffs over the internet. Ryan argues that Natalie knows nothing about the process of firing people, and his boss (Jason Bateman) assigns him to take Natalie with him on his upcoming travels to show her what it's like. As they travel together and become better acquainted, Natalie questions Ryan's philosophy, but Ryan is happy to remain in his niche and continue avoiding serious relationships. While traveling, Natalie's boyfriend dumps her by text message, leaving her shattered. When Natalie talks to Ryan about his refusal to consider a commitment to Alex in spite of their obvious compatibility as a couple, she becomes infuriated; she apologizes later, but soon afterwards they are both called back to Omaha to begin using Natalie's remote-layoff program instead of firing people face-to-face.
Instead of returning to Omaha, Ryan invites Alex to accompany him to his sister's wedding. His sister's fiancé grows cold feet, and Ryan is requested to use his motivational skills to persuade him to go through with the wedding. Although this runs counter to all of Ryan's personal ideals, he successfully argues that the important moments in life are seldom alone and the wedding proceeds as planned.
Back in Omaha, Ryan is less than thrilled to learn more about the online firing program and its systematic precision. He goes to deliver his "What's In Your Backpack?" speech at a prestigious convention in Las Vegas, but is unable to continue and walks out shortly after taking the stage. He hurriedly flies to Alex's home in Chicago. When she opens the door, it's apparent that she's a married woman with young children; stunned, Ryan leaves without saying a word. She later tells him on the phone that her family is her real life and he is simply an escape. On the flight home, the crew announces that Ryan has just crossed his ten million miles mark and the airline's chief pilot (Sam Elliott) comes out of the cockpit to meet Ryan.
Back in his office, Ryan calls the airline to transfer half a million miles each to his sister and brother-in-law so that they'll be able to fly around the world, but this generous action is temporarily delayed by his boss, who comes in and tells Ryan that one of the employees he and Natalie fired has killed herself. Natalie has already quit in shock after hearing the news and the company has put the remote-layoff program on indefinite hold. Ryan writes a glowing letter of recommendation for Natalie that helps her get a new and much more prestigious job in San Francisco. Impressed by her qualifications, the interviewer ask her why she didn't apply to his firm right after college instead of accepting a shady job firing people from Omaha. She finally confesses: it was for her desire to be closer to a boyfriend. The film concludes with Ryan giving a speech via voice over to a backdrop of clouds.
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