Ryan Bingham (Clooney) is a man who 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. For example, he criticizes those individuals who constantly try to carry a lot of photos from the past. He says that those attachments drag you and you cannot move forward with them. 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 (a feat managed only six times previously, according to Bingham, that will result in his receiving a card granting him lifetime Executive Platinum status with the airline and his name being imprinted on the side of an aircraft). 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 from Cornell named 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. During their travels, Natalie finds the layoffs to be an eye opening experience, albeit a negative one, as it's devastating for those being fired.
While on the road, Natalie's boyfriend dumps her by text message, leaving her shattered. Ryan and Alex take her with them to crash a tech-conference party at their hotel in Miami, which has her finally cut loose. When Natalie talks to Ryan the next day 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 in northern Wisconsin, and she accepts. He introduces her to his older sister Kara (Amy Morton) and his younger sister Julie (Melanie Lynskey), who explains that she and her fiancé Jim (Danny McBride) didn't have the money for a honeymoon; instead, they asked friends across the nation to take cardboard cutouts of the couple to different places and take pictures of them with touristy backgrounds, so "at least we have the photos." At the family meeting, Ryan is politely criticized by Kara for having been too distant with them. He awkwardly tries to resume his "man in the family" role by asking Julie about who will escort her down the aisle, but the sisters answer that they have already solved that by relying on Jim's uncle. Before the wedding, Ryan shows Alex his old high school. Their date is cut short when Kara calls with urgent news; Jim has cold feet, and Bingham must 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; Jim apologizes to Julie and the wedding proceeds as planned. Ryan and Alex enjoy attending the wedding together, but afterward Ryan finds that he is once again alone as Alex departs back to resume her own life.
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, and the two have a conversation. The captain notices that Ryan is so young to have traveled that impressive amount of miles, and then asks him where is he from. Ryan ponders the question for a moment and then answers: "I'm from here", meaning that indeed he has spent his entire adult life en route with no place to call home.
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 and the company has put the remote-layoff program on indefinite hold. Now Ryan is back onto the road.
Ryan writes a glowing letter of recommendation for Natalie that helps her get a new job in San Francisco. The interviewer asks her why such an obviously brilliant professional as she had previously passed up a number of more prestigious jobs at top firms to do some shady job in Nebraska. She finally acknowledges that she had done that career move just in order to be closer to a boyfriend.
The film concludes with Ryan giving this speech via voice over to a backdrop of clouds. "Tonight most people will be welcomed home by jumping dogs and squealing kids. Their spouses will ask about their day. Tonight they'll sleep. The stars will wheel forth from their daytime hiding places, and one of those lights, slightly brighter than the rest, will be my wingtip passing over."
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