Why do we say "Nothing ventured, nothing gained"?

Meaning:

You have to be willing to take risks to get anywhere.

Background:

The first known reference to this saying is in "The Reeve's Tale" (c.1476), one of the stories in Geoffrey Chaucer's The Canterbury Tales.

The Canterbury Tales is written in Middle English in a combination of verse and prose. The stories are told by a diverse group of men and women who are on a pilgrimage to Canterbury. Each night, a different member of the party tells a story in the hope of winning the prize of a meal at the inn when they return from their journey. We will never know which is the winning tale as Chaucer did not complete the collection. Apparently he had intended that each member of thirty pilgrims would tell four stories, two on the way to Canterbury and two on the way back, for a total of 120 but he ran out of steam and only wrote twenty-four stories, including "The Reeve's Tale."

At the time Chaucer penned his stories, a reeve was, in essence, an estate manager--the person appointed to manage the manor and its lands and to oversee its peasants. Oswald, the reeve of Chaucer's imagination, manages a large estate which makes considerable profits for both its master and for Oswald. Before becoming a reeve, Oswald had been a carpenter--a trade mocked in the previous night's story told by the Miller. So, Oswald responds with a story that mocks the Miller's profession, about two young men who set out to trick a miller. The story is bawdy and out of kilter with modern sensibilities so we will not repeat it here but it can be read in full in modern English translation at https://chaucer.fas.harvard.edu/pages/reeves-prologue-and-tale.

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