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  1. Consider Fitzgerald’s fate: He sells more books in a month today than he did in his entire life. His first novel was a smash hit yet he died a drunk failure. On his birthday, let’s understand the psychology of the tortured but transformative author who wrote THE GREAT GATSBY👇

  2. Fitzgerald also wrote The Curious Case of Benjamin Button. Button ages backward; Gatsby can’t let go of his past. Both literary experiments with time. The Great Gatsby ends with: “We beat on, boats against the current, borne back ceaselessly into the past.” But what’s in the past?

  3. In a 1936 essay HANDLE WITH CARE, Fitzgerald wrote: “My own happiness in the past often approached such an ecstasy that I could not share it even with the person dearest to me but had to walk it away in quiet streets.” The past offered happiness; the present, only disillusionment.

  4. In a 1938 letter to his daughter Frances, Fitzgerald wrote: “My generation of radicals and breakers-down never found anything to take the place of the old virtues of work and courage and the old graces of courtesy and politeness.” This tragic conservatism haunts Fitzgerald’s work.

  5. In This Side Of Paradise, his first novel, Fitzgerald wrote that to grow up in modernity is to “find all Gods dead, all wars fought, all faiths in man shaken.” All that’s left to do, Fitzgerald says, is to “follow love and pride.” Are they good guides worth following to the hilt?

  6. Fitzgerald wrote about his despair in a remarkably candid ESQUIRE essay THE CRACK-UP: “I saw that for a long time I had not liked people and things, but only followed the rickety old pretense of liking.” He slept on his “heart side” to slip into nightmares sooner.

  7. Fitzgerald became depressed when he realized he’d spent his whole life pretending. Edmund Wilson was his “intellectual conscience.” Another man dictated his “sense of the good life.” A third man shaped his “relations with other people.” Fitzgerald lived on borrowed answers…

  8. Despite being a formidable man of letters, Fitzgerald hadn’t reflected too deeply on life: “I had done very little thinking, save within the problems of my craft.” He saw within, found nothing: “There was not an "I" anymore - not a basis on which I could organize my self-respect.”

  9. When one blindly apes others, an emptiness grows where our soul could’ve lived: “It was strange to have no self—to be like a little boy left along in a big house, who knew that now he could do anything he wanted to do, but found that there was nothing that he wanted to do.”

  10. Fitzgerald felt that to even be nice was to “draw things” from a “conjurer's hat” that had been empty for a long time. Politeness was just a “sleight of hand.” He felt a “vast irresponsibility” for all obligations. Even for his own talent he became a “mediocre caretaker.”

  11. Fitzgerald was too agreeable, and to recover, he had to go dark. As this happened, he felt a “heady villainous” sensation. He stopped being "kind, just, or generous" as a matter of fact. He went home and threw away all the letters “that wanted something for nothing.”

  12. Another activity that helped Fitzgerald recover his mental balance: making “hundreds of lists.” The lists he made: “football players and cities, and popular tunes and pitchers, and happy times, and lists of women I'd liked, and of the times I had let myself be snubbed.”

  13. Why was making lists therapeutic for Fitzgerald? Because lists represent hierarchy, order our concerns, and infuse coherence in an otherwise messy psyche. A list is a mental building, each item on it a brick - a clarifying arrangement of priorities. When in doubt, make lists.

  14. Fitzgerald wasn’t content with either his books or his life. Yet his “convictions” are worth thinking about: passionate belief in order, a disregard of motives or consequences in favor or guesswork and prophecy, a feeling that craft and industry would have a place in any world

  15. What should a writer aim for? Scott Fitzgerald's answer is unimprovable: "An author ought to write for the youth of his own generation, the critics of the next, and the schoolmasters of ever afterward.”

Thank you for reading!

Fitzgerald wrote achingly beautiful prose on love, gave wise advice to his daughter in letters, and has great writing tips for us all. I collect 10 insights from Fitzgerald here.

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What video is a better use of time than the book it’s based on?

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“Education is simply the soul of a society as it passes from one generation to another” – G.K. Chesterton Here we discuss The Great Books and other art forms, share best practices for pursuing a Classical Education and help others to understand the immense value of a traditional Liberal Arts education. Education should be about so much more than just making money, it should also teach people how to live well and to love that which is most beautiful. Our sub exists to promote these ideas.
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