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I recently began reading Hemingway’s memoir, A Moveable Feast. In it, Hemingway and his contemporary Americans are described as a ‘lost generation’:

It was when we had come back from Canada and were living in the rue Notre-Dame-des-Chanps and Miss Stein and I were still good friends that Miss Stein made the remark about the lost generation. She had some ignition trouble with the old Model T Ford she then drove and the young man who worked in the garage and had served in the war had not been adept, or perhaps had not been serieux and had been corrected severely by the patron of the garage after Miss Stein’s protest. The patron had said to him, ‘You are all a generation perdue.’

’That’s what you are. That’s what you all are,’ Miss Stein said, ‘All of you young people who served in the war. You are all a lost generation.’

’Really?’ I said.

’You are,’ she insisted. ‘You have no respect for anything. You drink yourself to death ...’

’Was the young mechanic drunk?’ I asked.

’Of course not.’

’Have you ever seen me drunk?’

’No. But your friends are drunk.’

’I’ve been drunk,’ I said, ‘but I don’t come here drunk.’

’Of course not. I didn’t say that.’

’The boys patron was probably drunk at eleven o’clock in the morning,’ I said. ‘That’s why he makes such lovely phrases.’

’Don’t argue with me, Hemingway,’ Miss Stein said. ‘It does you no good at all. You’re all a lost generation, exactly as the garage-keeper said.’

What does this mean? How does one lose oneself, or even a whole generation? What is it that they have lost? And where did they lose it? In other words, what did Gertrude Stein mean by saying this and what did Hemingway mean by including this exchange and what does it mean in the later context of American history? More broadly, are there any other references to this in Hemingway’s work?

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I was surprised to learn that the Lost Generation is a literary term that refers to a number of writers from the post war era, including Hemingway, F Scott Fitzgerald and Sinclair Lewis. It doesn’t really answer my question in the depth that I would like but it does say that Hemingway used the term in the epigraph to his novel, The Sun Also Rises.

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This referred to a lack of purpose and drive which was a consequence of having witnessed pointless death on such a huge scale.

In the aftermath of the war there arose a group of young persons known as the "Lost Generation." The term was coined from something Gertrude Stein witnessed the owner of a garage saying to his young employee, which Hemingway later used as an epigraph to his novel The Sun Also Rises (1926): "You are all a lost generation." This accusation referred to the lack of purpose or drive resulting from the horrific disillusionment felt by those who grew up and lived through the war, and were then in their twenties and thirties. Having seen pointless death on such a huge scale, many lost faith in traditional values like courage, patriotism, and masculinity. Some in turn became aimless, reckless, and focused on material wealth, unable to believe in abstract ideals.
- Lost Generation - Writers Inspire

As the OP mentions in the question this term also exists in literature and refers to some writers and poets and authors who lived during this era.

In literature, the "Lost Generation" refers to a group of writers and poets who were men and women of this period. All were American, but several members emigrated to Europe. The most famous members were Gertrude Stein, Ernest Hemingway, F. Scott Fitzgerald, and T. S. Eliot.
- Lost Generation - Writers Inspire

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The idea of the “lost generation” is best seen in Hemingway’s The Sun Also Rises in which theme of emptiness looms large. The title itself, succinctly captures the idea in the Bible and in light of the biblical context, it is clearly pregnant with meaning. Here is the passage:

The words of the Preacher, the son of David, king in Jerusalem.

“Vanity of vanities,” says the Preacher; “Vanity of vanities, all is vanity.” What profit has a man from all his labor In which he toils under the sun? One generation passes away, and another generation comes; But the earth abides forever. The sun also rises, and the sun goes down, And hastens to the place where it arose. The wind goes toward the south, And turns around to the north; The wind whirls about continually, And comes again on its circuit. All the rivers run into the sea, Yet the sea is not full; To the place from which the rivers come, There they return again. All things are full of labor; Man cannot express it. The eye is not satisfied with seeing, Nor the ear filled with hearing. That which has been is what will be, That which is done is what will be done, And there is nothing new under the sun. Is there anything of which it may be said, “See, this is new”? It has already been in ancient times before us. There is no remembrance of former things, Nor will there be any remembrance of things that are to come By those who will come after. (Ecclesiastes 1:1-11, KJV)

The Hebrew word for “vanity” is הֶבֶל (hebel) meaning “vapor” or “breath” and is similar to the Hebrew habel meaning “emptiness” and can also denote a gentle breeze. All these definitions carry connotations of temporary, transient, or transitory—in keeping with the theme in TSAR; and the reoccurring motif of movement. The conversations tend to be quite trivial and often about what the group should do next, or where the group should go next—they are always on the move—that is, transient. These characters are living an empty, meaningless existence. The idea of loss of religion is also a theme. This passage speaks to that notion as well. “Life without God is in fact meaningless”—seems to be the central message of this passage. Even the sun itself is moving and transient as it “hastens” to “where it arose.” The sun שֶׁמֶשׁ (shemesh) denotes brightness, warmth, and life, but even it acts out the transient nature of life as it lives and dies every day. This passage also denotes the idea of the “lost generation.” The Hebrew דּוֹר (dowr) denotes “generation”; all; or many who “pass away” הָלַךְ (halak). It is interesting to note that הָלַךְ (halak) in Hebrew means “to go, walk, come, depart, proceed, move, go away; to die, live, manner of life.” The constant coming and going of the main characters in TSAR is clearly symbolic of spiritual death—“the lost generation.”

Sources:

Davidson, Benjamin. The Analytical Hebrew and Chaldee Lexicon. Hendrickson Publishers, 1981.

The Holy Bible (King James Version). Thomas Nelson Publishers, 1972

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Hemingway's generation was what William Strauss and Neil Howe called a "reactive" generation in their book Generations: A History of America's Future, 1584-2069. This is one of four generational "types" that rotate in an (almost) fixed sequence. (The most modern "reactive" generation is Generation X.)

The "reactive" generations follow "Idealist" generations who start intellectual awakenings and "consciousness revolutions" (the Great Awakeners, the Baby Boomers, the "Transcendenals of Lincoln and Hawthorne, and in the case of Hemingway, what S&H call the Missionary Generation (and what I call the "Rendezvous With Destiny Generation.") Such generations have a self-appointed mission: "No taxation without representation, or "make the world safe for democracy."

The young people of "reactive" generations are "tasked" with making these ideals come true (and paying the price, of say, Wilson's 14 Points.) As Gertrude Stein, (a "Missionary" woman) said, ‘All of you young people who served in the war. You are all a lost generation.’ They appear to have "no purpose and drive" (of their own), because they are busy serving the purposes and drives of other (older) generations.

And "you have no respect for anything means "You have no respect for us (Idealists)." There is an old saying that "A master is never a hero to his valet." Hemingway, Fitzgerald, and Lewis were all members of a common generation, born in the 1880s and 1890s.

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