Inside Hemingway’s Surprising Letter to Fitzgerald: A Stark Revelation About Battling Self-Doubt

Ever wonder if the masterminds behind history’s greatest art and literature ever felt like total failures? Spoiler alert: they did—big time. From the genius doodles of Leonardo Da Vinci to the tortured brushstrokes of Vincent van Gogh, even legends wrestled with an unshakable shadow of self-doubt. Enter F. Scott Fitzgerald, the iconic wordsmith who, in a moment of vulnerability, turned to his friend Ernest Hemingway for a brutally honest reality check after publishing Tender Is the Night. What followed was a raw, no-holds-barred letter that cut through ego and insecurities, reminding us all that even the greats struggle—and somehow manage to keep writing through the chaos. So, if you’ve ever stared at a blank page wondering if you’ve got what it takes, you might want to lean in and listen to what Hemingway had to say. LEARN MORE

It can be easy to forget that the creators of some of the world’s greatest works of art and literature were plagued by relentless self-doubt. Yet from Leonardo Da Vinci to Vincent van Gogh, some of the most legendary artists of all time have been crippled by a deep, near-inescapable feeling that they were failures. 

One member of this strange club is F. Scott Fitzgerald, now considered one of the giants of 20th-century literature. In 1934, just after publishing Tender Is the Night—his first book in nine years since The Great Gatsby—Fitzgerald reached out to his old friend Ernest Hemingway for feedback. 

It had been a difficult decade for Fitzgerald. His wife Zelda had been institutionalized in 1930, he was struggling financially, and his drinking had become excessive. Hemingway and Fitzgerald, meanwhile, shared a longtime friendship despite their differing beliefs and opposite personalities, and Hemingway responded to Fitzgerald’s inquiry with an uncompromisingly blunt missive. 

Hemingway’s Frank Advice to Fitzgerald

In his letter, Hemingway initially explains that he “liked” Tender Is the Night and also “didn’t”—a contradictory phrase that undoubtedly would have appealed to Fitzgerald’s intellectual sensibilities. (Fitzgerald, after all, once wrote that “the test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function” in his essay The Crack-Up, which detailed some of the insecurities Hemingway would go on to denounce). 

Hemingway then gets into the weeds of his message. In essence, he commands Fitzgerald to leave behind his self-absorbed obsession with what others think and to simply do what he is best at.

“For Christ sake write and don’t worry about what the boys will say nor whether it will be a masterpiece nor what,” Hemingway writes. “I write one page of masterpiece to ninety one pages of s**t. I try to put the s**t in the wastebasket.”

He goes on to advise Fitzgerald to use his personal pain as fuel for creativity, but to not become overly attached to his own self-pity. “Forget your personal tragedy,” he continues. “We are all bit**ed from the start and you especially have to hurt like hell before you can write seriously. But when you get the damned hurt use it—don’t cheat with it. Be as faithful to it as a scientist—but don’t think anything is of any importance because it happens to you or anyone belonging to you.”

In short, Hemingway seems to advise that the answer to creative self-doubt is to abandon the ego and return to the page and the craft, without being overly attached to where any of it will end up or how any of it will be perceived. 

“Scott, good writers always come back,” he continues. “Always. You are twice as good now as you were at the time you think you were so marvellous. You know I never thought so much of Gatsby at the time. You can write twice as well now as you ever could. All you need to do is write truly and not care about what the fate of it is. Go on and write.”

Abandoning excessive egoism is a core message of Buddhism and many other ancient faiths. It also may be an antidote for our modern era of endless self-optimization and branding. Clearly, it was a message that Hemingway thought his friend needed to hear in 1934, albeit wrapped up in a series of rather harsh and uncompromising machismo characteristic of the author.

Unfortunately, Tender Is the Night was the last novel Fitzgerald published during his lifetime. He died at just 44 in 1940 of a heart attack. Yet his work lives on, as does the evidence of his complicated relationship with another one of the 20th century’s great storytellers.

Hemingway and Fitzgerald’s Complex Friendship

Hemingway and Fitzgerald first met in a bar in Paris in April 1925, shortly after Fitzgerald published Gatsby. Hemingway was a journalist at the time and was still at the start of his literary career, and so admired Fitzgerald, who in turn apparently admired Hemingway’s hyper-masculine persona. They quickly formed a friendship based on their shared love of drinking—a lot of drinking—and writing.