The story follows Ryan Bingham, a seasoned traveler who spends most of his time flying around the country to deliver termination notices on behalf of corporations. Ryan enjoys his solitary lifestyle and finds comfort in his frequent flyer status and the perks that come with it.
Ryan’s life becomes more complicated when his company hires Natalie Keener, a young and ambitious employee who proposes a cost-cutting measure: conducting termination meetings via video conferencing to eliminate the need for travel. Initially resistant to the idea, Ryan is forced to take Natalie on the road with him to show her the ropes.
As they travel together, Ryan and Natalie develop a rapport, and Ryan begins to question his own priorities and values. He also forms a connection with Alex Goran, a fellow traveler he meets on the road. Despite his initial reluctance to pursue a romantic relationship, Ryan finds himself drawn to Alex and begins to open up to her about his fears and insecurities.
Meanwhile, Ryan’s sister’s wedding approaches, and he reluctantly agrees to attend, despite his aversion to commitment and emotional attachment. At the wedding, Ryan realizes the emptiness of his transient lifestyle and begins to reevaluate his priorities.
In a climactic scene, Ryan confronts his boss about the direction of the company and his own future within it. He also makes a bold decision regarding his relationship with Alex, ultimately choosing to pursue a deeper connection with her rather than continuing to prioritize his career and solitude.
The film ends with Ryan embracing the uncertainty of his future and taking steps to embrace the meaningful connections in his life, rather than running from them. He also comes to terms with the inevitability of change and the need to adapt and evolve in order to find true fulfillment and happiness.