Plot

Ryan's job is to travel around the country firing off people. When his boss hires Natalie, who proposes firing people via video conference, he tries to convince her that her method is a mistake.

Ryan Bingham is a corporate downsizing expert whose cherished life on the road is threatened just as he is on the cusp of reaching ten million frequent flyer miles, and just after he's met the frequent-traveller woman of his dreams.

Ryan Bingham flies around the country firing people. He's good at his job and is constantly in the air flying from one city to another. He's also an accumulator of frequent flyer miles and has a goal: he wants to get to ten million miles. His routine is interrupted by the arrival of Natalie Keener, who thinks the travel is unnecessary and the firings can be done through videoconferencing. Ryan's boss loves the idea, but wants Ryan to take Natalie on the road with him to show her how he does it. It proves to be a life lesson for Natalie after one of her counseling sessions goes wrong. Ryan also learns that some of the choices he's made have not always been the correct one.—garykmcd

Ryan Bingham's job is to fire people from theirs. The anguish, hostility, and despair of his "clients" has left him falsely compassionate, living out of a suitcase, and loving every second of it. When his boss hires arrogant young Natalie, she develops a method of video conferencing that will allow termination without ever leaving the office, essentially threatening the existence Ryan so cherishes. Determined to show the naive girl the error of her logic, Ryan takes her on one of his cross country firing expeditions, but as she starts to realize the disheartening realities of her profession, he begins to see the downfalls to his way of life.—The Massie Twins

Ryan Bingham works for Omaha-based Career Transition Counseling, whose contracts are in corporate downsizing. In other words, they fire people. Ryan is flying around the U.S. over three hundred twenty days of the year, which he feels is the best part of his job. He does whatever he can to rack up frequent flyer miles, the goal not to use them, but just to accumulate them to a specific number he has in his mind. A secondary job he has is to give motivational speeches on relieving one's life of excess physical and emotional baggage. He truly does believe what he espouses as he lives out of his carry-on suitcase (his apartment in Omaha is really in name only), he is not close to his siblings (although he does do a favor for his sister while on his travels), nor does he have or want a significant person in his life. Ryan's life may change when the company hires Natalie Keener, a young overachieving woman who recommends that the company change the nature of the work by conducting the "firings" via remote computer access. Ryan believes that Natalie does not fully understand the nature of the business, and as such, their boss, Craig Gregory, suggests that she accompany Ryan on a business trip. Ryan is also trying to protect his way of life, which now includes meeting up with a woman named Alex Goran whenever their flight schedules mesh. Like Ryan, Alex, who he met in an airport hotel bar, is constantly travelling for work, and is as equally turned on the by the concepts of "elite status" or "preferred member" as Ryan is.—Huggo

Ryan Bingham (George Clooney) works for the Career Transitions Corporation (CTC). He makes his living traveling to workplaces around the United States and informing workers of their dismissals in place of their employers, who fear doing it themselves. Ryan also delivers motivational speeches, using the metaphor "What's In Your Backpack?" to extol the virtues of a life free of burdens like relationships with people as well as things, arguing that the best way to live is to travel light, with little to hold you down.

Ryan relishes his perpetual travels. His personal ambition is to earn ten million frequent flyer miles with American Airlines. While traveling, he meets another frequent flyer, Alex (Vera Farmiga). They begin a casual relationship, meeting whenever they can arrange to cross paths. Ryan is unexpectedly called back to CTC's offices in Omaha, Nebraska. An ambitious, freshly graduated new hire, Natalie Keener (Anna Kendrick), is promoting a plan to cut costs by conducting layoffs via videoconferencing. Ryan argues that Natalie knows nothing about the actual process, live or not, as she has never fired anyone and does not know how to handle upset people. He plays the role of a fired employee to show her inexperience. His boss (Jason Bateman) assigns him to take Natalie with him on his next round of terminations, much to his annoyance. Throughout the rounds, Natalie is visibly disturbed by firing people face to face.

As they travel together and become better acquainted, Natalie questions Ryan's philosophy, but he is satisfied with his lifestyle. During the trip, Natalie is shattered when her boyfriend unceremoniously dumps her by text message. Ryan and Alex try to comfort her. Natalie later lectures Ryan about his refusal to consider a commitment to Alex in spite of their obvious compatibility, and becomes infuriated; she apologizes later, but soon afterwards they are ordered back to Omaha to begin implementing Natalie's program. There are problems during a test run; one laid-off man breaks down in tears before the camera, and she is unable to comfort him.

Instead of returning immediately to Omaha, Ryan convinces Alex to accompany him to his younger sister Julie's (Melanie Lynskey) wedding near Milwaukee, Wisconsin. Julie had him (and others) take photos of a cutout picture of her and future husband Jim (Danny McBride) in various places because they cannot afford a honeymoon trip. When Jim gets cold feet, Ryan's older sister talks Ryan into using his motivational skills to persuade Jim to go through with it. Although this runs counter to Ryan's personal philosophy of non-commitment, he persuades Jim that "everyone needs a co-pilot" and the important moments in life are rarely Unshared. The wedding takes place without any further problems.

Ryan begins having second thoughts about his own life. As he starts to deliver his "What's In Your Backpack?" speech at a convention in Las Vegas, he realizes he no longer believes it and walks off the stage. On an impulse, he flies to Alex's home in Chicago, Illinois. When she opens the door, he is stunned to discover she is a married woman with children; 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. When she asks him what he wants out of their relationship, he is unable to answer.

On his flight home, the crew announces that Ryan has just crossed the ten-million-mile mark. The airline's chief pilot (Sam Elliott) comes out of the cockpit to meet Ryan. He notes that Ryan is the youngest person to reach the milestone; Ryan, who had been preparing for that moment for a long time, shows little emotion.

Back in his office, Ryan calls the airline to transfer five hundred thousand miles each to the newlyweds, enough for them to fly around the world for their honeymoon. His boss then tells Ryan that a woman he and Natalie fired has jumped off a bridge, just as she warned them she would, and that when Natalie found out, she quit via text message. Ryan claims to have no memory of the employee making this threat. The company puts the remote-layoff program on hold because of government concerns, and Ryan is once again "back on the road".

Natalie applies for a job in San Francisco, California. The interviewer is puzzled as to why she chose to work for CTC, given her sterling qualifications; she tells him she followed a boy. Based on a glowing recommendation from Ryan, he hires her. The film concludes with Ryan standing in front of a vast destination board, looking up, and letting go of his luggage. Though he never was in the firing seat and never listened to the advice he frequently dispensed, his release of his luggage echoes a sentiment expressed by Natalie earlier.