Ryan Bingham works for a company that specializes in corporate downsizing, traveling across the United States to fire employees for companies unwilling to do it themselves. He revels in his detached lifestyle and aims to achieve a milestone of ten million frequent flyer miles. On the road, Ryan meets and develops a casual relationship with fellow frequent traveler Alex, forming a bond over their mutual love of travel and non-commitment. As he is summoned back to his company's headquarters in Omaha, he learns that Natalie Keener, a young and ambitious new hire, has developed a method to conduct firings via video conferencing, potentially grounding Ryan's cherished lifestyle.

Ryan is tasked with taking Natalie on the road to show her the intricacies of their job, providing her with real-world experience before the new system is fully implemented. Throughout their travels, Ryan begins to question his isolated way of life and develops an unexpected connection with both Natalie and Alex. His interactions with these women challenge his long-held beliefs about relationships, work, and personal fulfillment. Through their journey, Ryan confronts the complexities of human connection and reevaluates what truly brings him happiness and purpose.