The theme of life's meaning transitions from questioning its purpose, "what it was all about," to understanding how to live within it, "how to live in it." This change happens because the main characters are unable to rise above their mediocrity. They must dismiss the idea of living a heroic life as beyond their reach. "Nobody ever lives their life all the way up except bullfighters." Cohn replies, "I am not interested in bullfighters. That’s an abnormal life." Cohn envisions life romantically—pursuing literary success and thrilling adventures with a beautiful, titled mistress. However, the group scorns Cohn's ideals, and Brett eventually concludes that he is "not one of us." The true essence of life lies in the ability to manage one's finances wisely. This may take different forms, but only Jake, the Count, and to some extent Bill Gorton, succeed in doing so. Brett, and especially Mike Campbell (who remains an "undischarged bankrupt"), will never find happiness, even if they become wealthy, as they lack the skill to use money wisely.

Bill appreciates both exchange and practicality. When he first appears in the narrative, he wishes to buy Jake a stuffed dog, saying, "Simple exchange of values. You give them money. They give you a stuffed dog." Bill believes in using money to create memorable experiences and to reflect one's social standing. His motto is "Never be daunted." Opportunities for enjoyment, such as visiting a pub or purchasing a bottle, should be fully embraced.

Conversely, Jake is developing a more complex outlook, carefully tracking his spending to distract himself from his main issue of impotence. He states, "I paid my way into things that I liked, so that I had a good time. Either you paid by learning about them or by experience, or by taking chances, or by money. Enjoying living was learning to get your money’s worth and knowing when you had it. You could get your money’s worth. The world was a good place to buy in." He acknowledges that his perspective might change in five years. Essentially, "the lost generation" can find joy through sensible spending (even if they aren't rich) until normalcy returns and the war is behind them. A possible future philosophy is hinted at when Jake reads Turgeniev and feels he will remember the content as if it were his own experience. Turgeniev writes truthfully about life in a way Hemingway agrees with. "That was another good thing you paid for and then had." Here, the payment is the effort of reading literature, which can aid in recovering from the war.