The opening credits roll over a montage of aerial shots of the ground as seen from an airplane in flight, as Sharon Jones & the Dap-Kings sing "This Land Is Your Land." The plane lands and we see a series of talking heads -- people who have just been fired. Their reactions run the gamut from incredulousness and sadness to anger, and are directed at Ryan Bingham (George Clooney), who is sitting calmly behind a desk. He works for CTC, Career Transition Counseling. In a voice-over, Ryan introduces himself: "I work for another company that lends me out to pussies like Steve's boss, who don't have the balls to sack their own employees." There's a quick montage of retaliatory actions a disgruntled fired employee might engage in (pouring bleach in the coffee, sniper shooting), and we see Ryan offer a pat, sincere consolation to Steve, a fired employee.
In a hotel room, experienced traveler Ryan expertly packs his suitcase. We see him drop off his rental car at an airport, bypassing the vacationers in the airport to check in at the frequent flyer desk, and powering through security with practiced moves as his voice-over lyrically describes the airport as his home. In first class, the stewardess asks him, "Cancer?" He looks at her quizzically. "Cancer?" He is confused, and she holds up a soft drink can, repeating, patiently: "Can, sir?" He shakes his head quickly and politely declines.
Next, Ryan gives a motivational speech, "Unpacking Your Backpack," where he admonishes a thin crowd in a nondescript hotel meeting room to consider how uncomplicated their lives would be if they didn't have responsibility for so many things: knick-knacks, photos, furniture, homes, and relationships. "Imagine waking up tomorrow with nothing. It's kinda exhilarating, isn't it?" The crowd is underwhelmed. Back at the airport, Ryan strides into a frequent flyer lounge flashing his membership card, where he is cheerfully greeted. He calls his office and talks to Kevin, an assistant, who tells him that he has been invited to appear at GoalQuest XX in Las Vegas as a motivational speaker. Ryan is excited; GoalQuest is a very high-profile conference. He is transferred to his boss, Craig Gregory (Jason Bateman), who asks him to come back to Omaha by the end of the week for big news. In a Dallas Hilton bar, Ryan trades frequent traveler observations with an attractive blonde businesswoman, Alex Goran (Vera Farmiga). They compare perks cards, and she's impressed by his American Airlines Concierge Key. ("Carbon fiber?" she inquires. "Graphite," he responds modestly.) She mentions that she flies about 60,000 miles a year, and Ryan politely says, "Not bad." She challenges him to disclose his mileage number. The challenge turns into verbal foreplay as she teases him on the size of his number. "Is it this big?" (Holds hands a few inches apart.) "this big?" (Holds hands further apart.) He mentions that he has a lifetime mileage goal in mind, but won't say what it is. Later, they swap stories about the most outré places they have had sex, and she declares that she has done it in an airline lavatory on a regional flight. They end up in bed together, and later compare calendars to see if they will be in the same town sometime soon. She decides to return to her room, and he agrees that that would be the "ladylike thing to do."
The next morning, he goes through what is obviously a routine: his workout in the hotel pool, a shoe shine, and the airport. While waiting for his plane, he receives a call from his sister Kara (Amy Morton), who is discussing the wedding of their sister Julie (Melanie Lynskey). Kara is sending him a cardboard cutout of Julie and her fiancé because Julie wants him to take a photo of the cutout in Las Vegas at the Luxor pyramid. He reluctantly agrees.
Omaha: Voice-over: "Last year I spent 322 days on the road, which meant I spent 43 miserable days at home." Ryan enters his small studio apartment, which has less personality than a hotel room: minimal utilitarian furniture, no decorations. His neighbor, a diffident young woman, brings over a package that she has signed for: the cutout that his sister wants him to photograph. He invites his neighbor over, and she awkwardly declines, telling him that she is now seeing someone. Ryan is unconcerned.
At a staff meeting, Craig is chortling that the economic downturn has created a wonderful opportunity for their firm, and introduces Natalie Keener (Anna Kendrick), a fresh young up-and-comer who has recently graduated at the top of her class at Cornell. Natalie introduces an on-line monitor that will be used to fire people from a remote location over the internet, eliminating the need for human resource specialists such as Ryan to travel. Ryan is appalled at the impersonality of the process -- and, we suspect, at the loss of his travel privileges. After the meeting, he goes to Craig's office to protest. Natalie joins them, and Ryan tells her that she knows nothing of the realities of firing a person. She brightly tells him that she majored in psychology, and Ryan challenges her to fire him. She takes on the challenge, and tries to fire him, failing miserably. Later, Craig accuses him of not being a team player and becoming a dinosaur. Craig tells Ryan that Natalie will be accompanying him on the road for the next few days to learn the ropes, much to Ryan's chagrin.
At home, Ryan packs for another road trip -- his shelves are as sparse as his apartment, utilitarian, containing nothing that is not traveling business attire. He is chagrined when he realizes that he has to carry the cut-out, which does not quite fit into his luggage. At the airport, he checks in with his usual efficiency, and then sighs when he sees Natalie arriving with a large, impractical suitcase. He forces her to buy a suitcase that will fit in the overhead compartment, telling her that he flies over 370 days a year, and that not checking luggage saves him the equivalent of a week a year. He ruthlessly pares her packing, tossing things he deems unnecessary into the trash. In the security line, he gives her the benefit of his traveling experience: Never get behind families or old people and try to find an Asian, because Asians travel light, wear slip-on shoes, and therefore move through security faster. Natalie: "That's racist!" Ryan: "I stereotype -- it's faster."
St. Louis: Alex calls Ryan as Ryan and Natalie are heading for the car rental. She's in Atlanta, and they try to match up overlapping time somewhere. They agree to meet at SDF (Louisville). Ryan and Natalie enter another office and begin their job of firing people. Natalie is instructed to stay quiet and simply hand them their benefits package, but she can't resist piping up with an inanity when a man called Bob (J.K. Simmons) asks what his family is supposed to do when he is on unemployment. Ryan, who has taken the time to read Bob's resume, rescues the interview by helping him realize that this is an opportunity for him to follow his dream of being a chef. Bob leaves, resigned but less angry.
Ryan bypasses a long line of people to check in at the Hilton Honors desk. An irate customer protests that Ryan just waltzed to the front of the line, but a smiling desk clerk tells her, "We reserve priority assistance for our Hilton Honors members!" Ryan helpfully hands the customer a brochure, and, still irate, she snatches it from him. At dinner with Natalie, Ryan orders several dinners to use up his $40 per diem. Natalie is surprised, and he tells her that he tries not to spend a nickel that doesn't go towards his frequent flyer miles. She asks why, and he tells her that he is aiming for ten million miles. She scoffs at what she deems to be a meaningless hobby, but he points out that that he would be only the seventh person to attain that level, and goes on to describe the award: lifetime executive status, meeting the chief pilot, Maynard Finch, and getting his name painted on the side of a plane. Natalie is unimpressed, and declares that if she had those miles, she'd show up at the airport, pick a place, and go.
That evening, in bed, Ryan looks at his sister's wedding invitation. He receives text messages from Alex that quickly become sexually suggestive. He responds, smiles, and turns out the light.
The next morning, Natalie helps Ryan by taking a photo of the cutout in front of the St. Louis airport. She doesn't understand the significance of the airport, and Ryan explains "the Wright Brothers flew here!" and goes on to ask Natalie if she never wondered why Charles Lindbergh's plane was called Spirit of St. Louis. Dismissively, she tells him no, she never wondered.
Wichita: Another office. Another firing, but the employee is angry. Afterwards, Ryan tells Natalie that sometimes, they just need to vent. Natalie is taken aback, but wants to try firing the next person, who at first appears to take the news calmly, but then announces in the same calm fashion that "There's this beautiful bridge by my house. I'm going to go jump off it." Natalie is distraught, and races from the building. Ryan reassures her that people say all sorts of things while they are being fired, and never mean them.
Kansas City: They enter an office that has been decimated -- only a few employees remain, and the receptionist is resigned when she sees them. In the hotel, Ryan overhears Natalie talking to her boyfriend as she declares, "I don't even think of him that way -- he's OLD." Ryan is taken aback. Alex joins him, and they enter a hotel room.
Des Moines: Another office, another firing. Natalie is starting to feel the emotional strain.
Miami: Ryan is giving another motivational talk, which he continues with the same allusion to getting rid of human connections, because relationships are the heaviest components of their lives. He declares, "The slower we move, the faster we die . . . we're sharks, we have to keep moving." Returning to the hotel, Natalie challenges Ryan about never getting married. He declares he is never getting married, and invites her to try to sell him on the idea of marriage. He's not buying. As they continue the discussion in the hotel lobby, Ryan wraps up the argument by declaring "make no mistake, we all die alone." Natalie suddenly dissolves in great sobbing tears and announces that her boyfriend, Bryan, has left her. As she falls sobbing into Ryan's arms, he sees Alex descending the stairs. Ryan introduces Alex to Natalie, and over drinks, Alex commiserates with Natalie: "He broke up with you by text? What a prick!" Ryan slyly agrees: "Almost as bad as being fired by internet." Natalie glares at him. Natalie goes on to tell them that she moved to Omaha to follow Bryan, giving up a good job offer in San Francisco, and goes on to lament that no matter how much success she might have professionally, it won't matter unless she finds the right guy. She has a mental schedule of deadlines that she had hoped to accomplish, and earnestly declares that she could have made her relationship with Bryan work because he met most of her requirements. Alex and Ryan smile and tell her that deadlines pretty much go out the window after a certain age. Alex goes on to explain that at 34, her expectations for a man have radically changed and describes the kind of man she'd like. Ryan listens with interest. Natalie observes that "that's depressing. We should just date women." Alex says, matter-of-factly, "Tried that. We're no picnic ourselves," to Ryan's surprise. Natalie says that she doesn't want to settle, and Alex tells her that she's young, so settling seems like failure. Natalie declares, earnestly, that is IS failure, by definition.
As they return to their rooms, Natalie asks what the plans for the evening are. Alex and Ryan are taken aback and had obviously not expected to include her in their plans. Ryan announces that they are going to hit the party for the tech conference that is being held in the hotel. Natalie says that she didn't know they were registered, and Alex and Ryan hem and haw until Natalie realizes that they are planning to crash the party, at which point she enthusiastically declares, "I'm in!" They casually walk up to the registration desk, grab some unclaimed badges, and enter the party. Natalie has inadvertently picked up a name tag for Jennifer Chu, but Ryan assures her that no one will notice. Natalie quickly downs a few drinks and begins to mingle, meeting a man called Dave. (This is a reference to Natalie's list of preferences in a boyfriend -- one of the odder items was "a one-syllable name like Matt or ... Dave.") Ryan and Alex dance. The MC comes on stage to sing and gets the crowd amped up. Later, Ryan offers Alex his hotel room key, "the key to my place," and Alex takes it, commenting lightly that she didn't realize they were at that point in their relationship. On an evening boat ride with other members of the conference, Natalie sings karaoke and Ryan and Alex sit at the back of the boat talking. Alex tells Ryan that she never has a chance to act this way at home, and asks him about his motivational philosophy: "Is the bag empty because you hate people or you hate the baggage that they come with?" He comments that recently, he's been thinking about emptying the backpack, and what he'd put back in it. He smiles, they kiss and at that moment, the boat loses power. A speedboat rescues them and ferries them to shore, where they have to splash through the surf to the beach. Laughing and drenched, the crowd scurries into the hotel. The next morning, Ryan wakes to see Alex finishing getting dressed -- she has stayed the night. She says that if she catches a standby, she can make a meeting in Cincinnati. Ryan looks momentarily disappointed, and she chides him playfully, "Oh, I made you feel cheap!" They laugh, and as she leaves, Ryan tells her, "Hey -- I really like you."
At breakfast at a poolside table, Natalie tries to apologize for what she might have said or done the night before, and Ryan tells her that it was good to see her cut loose. He then asks her if she woke him up or slipped out (referring to the man she picked up at the party). Natalie admits that she just slipped out, and Ryan observes, "the protocol's always tricky."
As they are taking another picture of the cutout against the Miami skyline, Natalie asks Ryan questions about Alex, finally asking, "so, what kind of relationship do you have?" He tells her that it's casual, and Natalie asks if there's a future. Ryan tells that he hadn't thought about it, but Natalie becomes annoyed. Ryan tries to explain: "You know that moment when you look into someone's eyes and you can feel them staring into your soul and the whole world goes quiet just for a second?" Natalie nods, "Yes!" Ryan declares, "Yeah, well, I don't." Angrily, Natalie throws down the cutout on the dock and declares that he's an asshole, Alex might be a chance at a real relationship, and then goes on to tell him that his philosophy is bullshit, he has a "cocoon of self-banishment" and that he has set up a way of life that makes it impossible for him to have any kind of human connection. She storms off, and the cutout blows into the water. Ryan tries to reach it, but falls into the water, too. Back in his room, he carefully blow dries the picture, but safely tucked in the suitcase on the way to Detroit, it is a bit worse for wear.
Detroit: Ryan warns Natalie that Detroit is a rough town and that the employees are touchy and will be difficult. When they enter the office, Ryan is surprised to see a computer monitor sitting on the table. Craig greets them from the screen -- he has arranged for a trial run of the internet-based firing procedure. They will be at a desk in the next room, but will only talk to the employees via screen. Natalie takes the first employee. At first, he is belligerent -- they can hear him bellowing in the next room through the thin walls -- but he later starts to sob disconsolately. Natalie is distressed, but hides it behind some stock encouraging phrases. She sends the employee away, and takes a deep breath. Craig has been monitoring the exchange, and is thoughtful. Ryan tells her, unconvincingly, that she did good as she looks forlornly at the list of employees -- this was the first of over fifty employees that will be released.
In the parking lot, Natalie leans against the car as Ryan talks to Craig, trying to convince him that they are still needed on the road. After the conversation, he resignedly tells Natalie that Craig has called them off the road: "We're going home." At the airport, Ryan stares out the large plate glass window, gazing at an airplane that has a large white area on the side, just waiting for a name to be painted on it. He looks at his sister's wedding invitation, and realizes that the date is this weekend and he has never returned the RSVP card. As they walk through the airport, Natalie tries to apologize for what she said about Alex, and Ryan ungraciously accepts her apology. Suddenly, he turns and tells Natalie that he will meet her in Omaha, but he's got to catch another flight.
Las Vegas: Ryan meets Alex and gets the requested photo of the cutout in front of the Luxor pyramid. Ryan invites Alex to his sister's wedding in Wisconsin. Surprised, Alex demurs, but finally agrees, and they fly into Milwaukee.
Northern Wisconsin: At the Chalet, a pseudo-Tyrolean motel, Ryan and Alex wait in the check-in line. Seeing a clerk behind the desk, Ryan asks her if she is free, but she condescendingly tells him, "This line is only for members of our Matterhorn program!" As he enters his room with Alex, his sister Kara comes out of her room, and he introduces Alex to Kara. Kara is surprised: "Ryan has told me . . . nothing about you." She tells him that she is staying at the hotel because she and her husband are having a trial separation, and reminds him of the rehearsal dinner that evening. At dinner, Julie is pleased to see Ryan and meet Alex. She proudly shows off a small, diamond chip ring that her fiancé Jim designed, and introduces Jim (Danny McBride), who is friendly in an awkward sort of way. Ryan offers her the photos that he has taken, and she asks him to pin them to a map that contains dozens and dozens of photos. Ryan has a hard time fitting his in. They explain that all of Jim's money is tied up in a real estate investment and made a honeymoon unfeasible financially, so the photos would be the next best thing.
After the dinner, Ryan offers to walk Julie down the aisle the next day since their dad isn't around, but embarrassed, she gently refuses, telling him that Jim's uncle will be escorting her. Ryan is somewhat hurt, but puts a good face on it and tells her that he just wanted to make sure she was covered. Julie is distressed that she might have hurt his feelings but when he asks when he should be at the church, she tells him, "Well, guests are supposed to be there at 5:00 so, 5:00 would be good," again relegating him to the status of a mere guest.
The next day, Alex and Ryan break into the local school so that Ryan can show her around. He points out his state basketball championship photo in the trophy case. Alex is surprised, and they end up kissing on the make-out stairs behind the gym. They sit down to watch a practice, but his cell phone rings: It's Kara, who tells him that hes needed at the church.
Alex drops him off at the church and returns to the hotel to grab his suit. Julie is distraught because Jim has gotten cold feet. Kara wants him to talk to Jim, but Ryan points out that he might not be the best one, because his job is to tell people how to avoid commitment. "What kind of fucked up message is that?" exclaims Kara. "It could have helped you," he retorts, referring to her separation, but reluctantly agrees to talk to Jim. He finds him in a Sunday school classroom reading The Velveteen Rabbit. Jim tells him that he began to think about what his life was going to be like: house, children, jobs, losing his hair, and then dying, and wonders what the point is. Ryan observes that a good marriage is something that people aspire to, but Jim points out that Ryan was never married, and that he seems happier than anyone else he knows. Ryan agrees that there's no point to it all, but points out that the most important moments of his life had other people involved, and observes that life is better with company, with a co-pilot. Jim accepts this, and then asks "What's it like out there?" Ryan admits that Julie is upset. Jim comes out and apologizes to Julie, asking her "Will you be my co-pilot?" Julie tearfully agrees, and the wedding proceeds. Alex and Ryan hold hands during the vows, and dance intimately at the reception.
At the airport, Alex asks when she will see Ryan again and Ryan tells her that she's going to have to come visit him, since he's been essentially grounded. She moves to her gate and tells him to "call me when you get lonely." As she walks away, he calls out, "I'm lonely." She laughs, and keeps walking. In Omaha, back at his apartment, he puts his things away, and looks around, dissatisfied. He opens the refrigerator to reveal an impressive collection of airline miniature booze bottles in the refrigerator door.
At the office the next morning, Natalie proudly shows him around the call center that is being beta tested, and comments that the workers are called "termination engineers. I wanted to call them Terminators, but was that bumped by Legal." "I can't imagine why," Ryan responds drily. Ryan sits at a desk and distastefully tries on a headset. He checks the internet for the schedule for GoalQuest XX, and sees when he is scheduled to speak.
Las Vegas: Ryan prepares for his speech, and as he is introduced to a crowd of several hundred, he takes the podium with his backpack. He begins the spiel that we have heard before but then stops and gazes out over the audience. He looks down at the podium, shakes his head ruefully, excuses himself, and walks out, to the consternation of the event organizers. He dashes through the airport and catches a flight to Chicago, where he arrives in the evening.
Chicago: In a hurry, Ryan steps out of his routine and drives away without giving the car clerk his rewards card. He pulls up in front of Alex's townhouse and rings the doorbell. Alex comes to the door. She is shocked as he says, smiling, "So, I was in the neighborhood . . ." Suddenly, he hears children arguing and we see them running in the hall behind Alex. Ryan begins to back away, and with a stricken look on Alex's face, we hear a male voice ask, "Who's at the door, honey?" She closes the door gently as she responds, "Just someone asking directions."
At the hotel, Ryan sits on a bed in a darkened room with a drink, staring out into the evening. On the train to the airport the next morning, he receives a call from Alex, who demands, "What were you thinking, showing up at my door like that?" He protests that he didn't know she was married, and she declares that he could have seriously messed up her "real life," and that she thought he understood. He said that he thought he was part of her real life, and asks her to help him understand. She tells him that he is an escape, an escape from their normal lives, a "parenthesis." "A parenthesis?" he repeats, dully. Alex is unapologetic. "Well, what did you want? If you want to see me again, give me a call." He hangs up on her gently.
In the air: Returning to Omaha, Ryan is gazing out the window when the flight attendant comes on the intercom to excitedly announce that they are flying over Dubuque, which means that a startled Ryan has hit the 10 million miles mark. Champagne is brought for all the first class passengers, and Chief Pilot Maynard Finch (Sam Elliott) greets Ryan. He sits in the seat next to Ryan and congratulates him, telling him that he's the youngest yet to get to 10 million. He pulls out the special silver card, engraved Ryan Bingham, #7, and presents it to Ryan, telling him that they really appreciate Ryan's loyalty. Ryan is speechless, and tells the Captain that he forgot what he always wanted to say at that moment. The Captain asks him where he's from, and Ryan, looking down, says softly, "I'm from here."
Omaha: In his office, Ryan looks at his card, and, making a decision, dials the number on the card. He is greeted with a cheery "Good morning, Mr. Bingham!" Surprised, he asks how they knew it was him, and is told that it's his dedicated line. He begins to make arrangements to transfer miles to Julie and Jim for an around-the-world trip, which costs half-a-million miles each.
Craig comes into his office and asks him if he remembers a Karen Barnes whom Natalie fired. Ryan says that they have fired dozens of people, and he doesn't remember. Craig tells him that Karen jumped off a bridge and killed herself, and he needs to know if she gave any indication of her intentions, which could get them into trouble legally. Ryan says he doesn't remember anything, and asks if Natalie is all right. Craig tells him that Natalie quit by sending him a text message. "Fucking nice, right? Nobody has any manners anymore," he grouses, and goes on to tell Ryan that he is returning the workforce to the field.
San Francisco: Natalie is interviewing for the job she was offered when she first graduated from Cornell. The interviewer asks her why she went to Omaha, and she reluctantly admits that "I followed a boy." After a few searching questions, the interviewer shows Natalie a letter of recommendation that he has received from Ryan. The letter is glowing, and the interviewer offers her the job.
A montage of interview clips follows. Employees whom we have seen being fired throughout the movie are in some sort of interview/counseling session. Each in their own way, they explain that while losing their job was difficult, it was made easier by the support of their friends and families.
Ryan enters an airport, suitcase in tow, and comes to stand in front of a large Departures and Arrivals board, gazing at the flight details. He releases the suitcase and stands in front of the board with no baggage. We hear Ryan's voice-over: "Tonight, most people will be welcomed home by jumping dogs and squealing kids. Their spouses will ask about their day, and tonight they'll sleep. The stars will wheel forth from their daytime hiding places and one of those lights, slightly brighter than rest, will be my wingtip passing over." The credits roll over a view of early evening blue clouds as seen below from an airplane, with a faint sunset in the far distance.