Creative people are highly sensitive, if not insecure. 

Ernest Hemingway is a surprising example of a creative person whose sensitivity would often cross the threshold into insecurity, especially in his early years as an aspiring novelist. 

When most people think of Hemingway, they think of a Bunyan-esque character who, in addition to penning some of the great American novels, fought bulls, shot lions, punched-out professional boxers, stole urinals, drank the heaviest of drinkers under the table and survived everything from gunfire to plane crashes to anthrax. 

However, the fearless Hemingway showed his throat in a letter he wrote to the poet Ezra Pound back in 1924.

*Hemingway is typing now*

Throughout the letter you’re about to read, which appears in The Letters of Ernest Hemingway, I made several notes (squeezed between pairs of parentheses) where I felt his writing needed a bit of context. 

"Dear Ezra—

Here, at 900 meters above the Nivel del Mare on the Spanish side of the Pyrenees is a good place to observe the ruin of my finances and literary career. Shit. I appeared in the bull ring on 5 different mornings—was cogida (Spanish for “fucked”) 3 times—accomplished 4 veronicas (Spanish for “victory”) in good form and one natural with the muleta (the little red cape that matadors wear), the last morning, received contusions and abrasions in the pecho (Spanish for “chest”) and other places, was drunk twice, saw Bill (I believe he is referring to Bill Bird here, an American journalist who ran a small press in Paris) drunk twice… We haven't enough pesetas (the basic currency in Spain) now to pay our hotel bill and don't know how we'll get away from here.

… Having been bitched financially and in a literary way by my friends I take great and unintellectual pleasure in the immediate triumphs of the bull ring with their reward in ovations, alcoholism, being pointed out on the street, general respect and the other things Literary Guys have to wait until they are 89 years old to get. The Plaza is the only remaining place where valor and art can combine for success. In all other arts the more meazly and shitty the guy, I.E. Joyce, the greater the success in his art…

Then when a guy has a few decent human instincts like yourself what do they do to him? I wish to hell I was 16 and had art and valor… I am going to have to quit writing because we haven't any money. The Transatlantic killed my chances of having a book published this fall and by next Spring some son of a bitch will have copied everything I've written and they will simply call me another of his imitators. Now we haven't got any money anymore I am going to have to quit writing and I never will have a book published. I feel cheerful as hell. These god damn bastards.

See you about the 27th of the month.

Love to Dorothy—

Hem."

In Hemingway’s letter to Ezra, we have to squint to recognize the confident (if not arrogant) novelist who would later write The Sun Also Rises, A Farewell To Arms and For Whom The Bell Tolls. Instead, we see an insecure twenty-something down on his luck, who seems more interested in dramatizing his failures as a writer to the point of fiction rather than writing anything that remotely resembles fiction. 

But, as we’ll soon discover, Hemingway was far from alone in his insecurity. 

The more creative the person, the more insecure. 

Countless creatives have voiced feelings of insecurity. 

The actress Kate Winslet once admitted that some mornings before going off to shoot scenes for a film, she thinks she’s a fat, ugly fraud that is sure to get fired (this is coming from a once-in-a-generation talent who has won Emmys, Grammys and Academy awards). 

Then, of course, there’s Tennessee Williams, a novelist who oozed confidence from every pour in his body but once admitted, “I don’t believe anyone ever suspects how completely unsure I am of my work and myself and what tortures of self-doubting the doubt of others has given me.”

Brain scientists will tell you that Winslet, Williams and Hemingway’s deep-seated insecurities make sense on a scientific level. 

Apparently, feelings of insecurity light up neurons in our brains associated with creativity. I’m not a neuroscientist so I’m not going any further down that particular rabbit hole but it’s clear that there is some correlation between insecurity and creativity. 

It becomes a question of the chicken or the egg. 

Are all insecure people creative? Or, are all creative people insecure? 

I’d guess the latter. 

While Shel Silverstein was working at Playboy drawing cartoons, he needed constant reassurance from Hugh Hefner. Despite his work regularly appearing in a magazine receiving international attention, Shel was deeply insecure. 

In her biography on Shel Silverstein, Lisa Rogak writes, "After Shel delivered a new batch of cartoons for Hef to review, he couldn’t work up the courage to ask Hef if he had seen the cartoons yet, and since Hef was so preoccupied with the magazine, he didn’t bring up the cartoons either. A curious passive standoff occurred, at least in Shel’s mind.”

Apparently, Shel would get so intensely insecure and paranoid because of Hefner’s silence surrounding his work, that he was ready to give up his career as a cartoonist altogether. 

Eventually, when Shel finally did see Hefner, he would have a meltdown. Hefner would look at him with utter confusion, explaining to Shel that he hadn’t yet had the chance to look over his latest batch of cartoons. Shel would then settle down and get back to drawing more cartoons. 

How can creative people feel more secure in themselves and their work? 

Truth be told, I think there will forever be a part of all creatives that doubt themselves and their work. 

Neil Gaiman tells an incredible story of a time he was at a dinner party of sorts and found himself in conversation with an older gentleman who expressed to the writer he didn’t belong there; that he felt like an imposter. 

After conversing with him for a bit, Gaiman realized the man suffering from imposter syndrome was none other than Neil Armstrong. Reflecting on the experience, Gaiman wrote, "And I felt a bit better. Because if Neil Armstrong felt like an imposter, maybe everyone did. Maybe there weren’t any grown-ups, only people who had worked hard and also got lucky and were slightly out of their depth, all of us doing the best job we could, which is all we can really hope for.”

I’m personally of the opinion that all creative people are a little bit insecure because they are constantly exposing themselves to great creative work. 

I’m not alone in this sentiment. 

Ira Glass, the mastermind behind some of the most popular podcasts of all time This American Life, Serial and S-Town, once shared an incredibly inspiring perspective on creativity…

“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know it's normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take a while. You’ve just gotta fight your way through.”

This “gap” that Glass is describing is the reason for a creative person’s insecurity. When a writer writes after having read Hemingway, he is going to feel insecure. When an actor acts after having watched Winslet, she is going to feel insecure. But, the only way to become a great creative person is to read Hemingway and watch Winslet so you can recognize great work when you see it; when you create it. 

A creative person’s insecurity is simply an indicator of great taste; and great taste is breeding ground for tremendous creative potential.

Godspeed,