Walter Mitty is a negative assets manager at Life magazine who daydreams of adventures and has a crush on a coworker named Cheryl.
Mitty works with photojournalist Sean O’Connell, whose images are highly regarded.
O’Connell has sent Mitty his latest negatives and a wallet as a gift in appreciation of Mitty’s work. O’Connell believes negative #25 captures the “quintessence of life” and that it should be used for the cover of the magazine’s final print issue as it converts to online status.
The negative is missing, however, and Walter is forced to stall for time with corporate transition manager Ted Hendricks, who is handling the downsizing.
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While viewing the other negatives outside Life‘s offices, Cheryl approaches Mitty and suggests that he think of the negatives as clues to Sean’s location. They look at three of them, including one of a person’s thumb with a unique ring on it, and another of a curved piece of wood. A third picture of a boat leads Mitty to determine that O’Connell is in Greenland. Mitty promptly flies there to find him.
A bartender in Nuuk explains that O’Connell left on a ship. To find him, Mitty would need to go on the postal helicopter, and the pilot is drunk.
Mitty recognizes the pilot’s thumb with the unique ring and realizes he is on the right track. He at first declines to fly with the intoxicated pilot, but imagines Cheryl singing “Space Oddity”, gains a new confidence and boards the helicopter.
Nearing the ship, Mitty learns the helicopter cannot land upon it. Misunderstanding the pilot, instead of jumping into a dinghy boat nearing to catch him, Mitty aims for the main vessel and misses and falls in the ocean. He splashes down into ice-cold, shark-infested waters, losing a box of ship-to-shore radio components before being brought aboard.