5 Lessons from The Great Gatsby School of Writing

The cover of the first edition of The Great Ga...
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If you should ever fall out of love with writing, read a little F. Scott Fitzgerald. That will surely rekindle the flames.

I’ve been reading The Great Gatsby in preparation for this week’s film premiere. There’s nothing like re-reading a book you loved in high school or college — a decade or two of real-world experience adds a whole new dimension to these stories.

But one thing that hasn’t changed for me is Fitzgerald’s heartbreakingly beautiful prose. My stepfather once said that Hemingway was great, but Fitzgerald could write circles around him. Truth.

He makes me want to be a better writer. More precise, more elegant, more poetic. And while it may be a stretch to apply lessons from Fitzgerald to business writing, there is at least some inspiration to be drawn from his soaring style. If not in an everyday email or memo, perhaps in a special speech.

Here are a few of the many passages I highlighted in my iBook, and what we can learn from them.

Power Verbs

In Fitzgerald’s world, trains plunge, stars stir, houses crouch and light volleys and hums:

  • The exhilarating ripple of her voice was a wild tonic in the rain.
  • [T]he electric trains, men-carrying, were plunging home through the rain from New York.
  • A universe of ineffable gaudiness spun itself out in his brain while the clock ticked on the washstand and the moon soaked with wet light his tangled clothes upon the floor.
  • It was dark here in front; only the bright door sent ten square feet of light volleying out into the soft black morning.
  • The quiet lights in the houses were humming out into the darkness and there was a stir and bustle among the stars.
  • [A] hundred houses, at once conventional and grotesque, crouching under a sullen, overhanging sky and lustreless moon.

No, you don’t want to choose words that call too much attention to themselves and distract from the point you’re trying to make, but it’s worth putting your imagination to work to explore choices beyond the ordinary.

Impossible Precision

Oh, to be able to capture a thought so precisely and elegantly!

  • He hadn’t once ceased looking at Daisy, and I think he revalued everything in his house according to the measure of response it drew from her well-loved eyes.
  • There must have been moments even that afternoon when Daily tumbled short of his dreams —¬†not through her own fault, but because of the colossal vitality of his illusion. It had gone beyond her, beyond everything.
  • He stretched out his hand desperately as if to snatch only a wisp of air, to save a fragment of the spot that she had made lovely for him. But it was all going by too fast now for his blurred eyes and he knew that he had lost that best part of it, the freshest and the best, forever.

The tip here, I’m afraid, is “be a genius.”

Metaphor & Analogy

I have a well-documented issue coming up with decent analogies. Fitzgerald takes figurative leaps with the language that dazzle.

  • Out of the corner of his eye Gatsby saw that the blocks of the sidewalks really formed a ladder and mounted to a secret place above the trees — he could climb to it, if he climbed alone, and once there he could suck on the pap of life, gulp down the incomparable milk of wonder.
  • [M]y underwear kept climbing like a damp snake around my legs and intermittent beads of sweat raced cool across my back.
  • From the ballroom beneath, muffled and suffocating chords were drifting up on hot waves of air.
  • I was thirty. Before me stretched the portentous, menacing road of a new decade.

Never underestimate the power of a good analogy.


Fitzgerald’s words move. With the help of alliteration and finely tuned rhythm, they leap and tumble, propelling you forward through the story.

  • So we drove on toward death through the cooling twilight.
  • All night the saxophones wailed the hopeless comment of the Beale Street Blues while a hundred pairs of golden and silver slippers shuffled the shining dust.
  • So when the blue smoke of brittle leaves was in the air and the wind blew the wet laundry stiff on the line I decided to come back home.
  • In his blue gardens men and girls came and went like moths among the whisperings and the champagne and the stars.

The dramatic pause is an important way to land a point, but speeding things along can also be effective in creating momentum and excitement.

Ending With a Bang

By the time we’re done writing, we’re often too wiped out to come up with a decent conclusion. But other than the introduction, it’s probably the most important part of a presentation or any written work.

So I’ll leave this one to the master: the closing words¬†to Gatsby (spoiler alert!) stand among the finest in modern literature:

So we beat on, boats against the current, borne back ceaselessly into the past.


3 thoughts on “5 Lessons from The Great Gatsby School of Writing

  1. “Be a genius”, indeed. In my case, “Words spin through his mind like a twister exploding across the open plains leaving a trail of thoughts chaotically strewn the page.”
    Thanks for sharing these simple yet grand ideas!

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