When in doubt, read this.

I am not in a good place. And I am no writer.

In Conclave, Ralph Fiennes plays a British cardinal by the name of Thomas Lawrence. After the sudden passing of the pope, Cardinal Lawrence is tasked with overseeing the election of his successor.

It’s one of the oldest, most sacred elections in the world. Over one hundred cardinals gather in the Sistine Chapel and swear an oath of secrecy. They are cut off from all outside communication. No phones. No media. No newspapers.

The cardinals have assembled to discern God's will.

On the first day of the election, Cardinal Lawrence decides to go off script and speak from the heart. You don’t have to be religious to see the beauty in his monologue…

“There is one sin which I have come to fear above all others: Certainty. Certainty is the great enemy of unity. Certainty is the deadly enemy of tolerance. Even Christ was not certain at the end. ‘My God, my God, why hast Thou forsaken me?’ he cried out in his agony at the ninth hour on the cross. Our faith is a living thing precisely because it walks hand-in-hand with doubt. If there was only certainty and no doubt, there would be no mystery—and therefore no need for faith. Let us pray that God will grant us a Pope who doubts.”

Five hundred years before Cardinal Lawrence stood beneath the Sistine Chapel and preached about the dangers of certainty, a young Michelangelo was painting that very ceiling—and doubting himself every step of the way.

For nearly four years, Michelangelo labored on scaffolding, his head thrown back and his arm pointed skyward as if gazing at God. In 1509, exhausted and miserable, he wrote an anguished poem encapsulating the experience…

“I am not in a good place. And I am no painter.”

Upon completion of the Sistine Chapel, Michelangelo wrote to his father…

“I have finished the chapel I have been painting: the Pope is very well satisfied. Other things have not turned out for me as I’d hoped. For this I blame the times, which are very unfavorable to our art.”

Reading that excerpt now, it’s almost comical.

Michelangelo was 33 years old when he made the first brushstroke on the Sistine Chapel. He was 37 years old when he made his last. He had just completed one of the greatest artistic achievements in human history. But, he was consumed with everything he hadn’t achieved.

Doubt is everywhere. No matter the artist. No matter the medium.

Ernest Hemingway, early on in his career, wrote in a letter to the poet Ezra Pound…

“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.”

Shel Silverstein nearly quit every time he submitted a cartoon to Playboy.

In A Boy Named Shel, 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.”

Shel would get so insecure and paranoid by Hefner’s silence surrounding his work, 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 reassure Shel that he hadn’t yet seen his latest batch of cartoons.

Shel would then settle down and get back to drawing more cartoons.

And then, of course, we must consider the surprising run-in Neil Gaiman had with an individual who shared his first name.

Gaiman once attended a gathering of extraordinarily accomplished people.

While there, he struck up a conversation with an elderly gentleman. He confessed to Gaiman that he felt like an impostor. He looked around the room—at all the brilliant people—and he wondered what on earth he was doing there.

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, of course, have very little in common with Armstrong, Silverstein and Michelangelo. Admittedly, it feels a bit ridiculous to even mention my name in the same breath as theirs. However, like the creatives who came before me, I do doubt myself every day.

Each time I sit down to write a poem, a song, an ad or an essay like the one you’re reading now, the doubt creeps in…

“Stop playing pretend. You’re washed-up; a has-been. Look at you, you delusional fuck. You’re not a poet. One Minute, Please? was a flop. After Her was a flop. Guillotine was a flop. How much money did you pour into publishing those books? Ten thousand dollars? Twenty thousand dollars? Let’s not get started on the albums. You’ve got a voice that sounds like a rusty saw tearing through bone. What’d you get this month? 80 listeners? 90 listeners? 100 listeners? Oh, but there is always advertising, right? You’re an adman. Shut the hell up. You try to turn every ad into a piece of art. But, you’re a failing artist. So, what does that make your advertising? You are nothing more than a mediocre creative whore.”

I thought the doubt would ease the older I got, but it has only gotten worse.

I tend to combat this self-doubt by doing a great deal of self-mythologizing. I tell myself silly little lies. If I say aloud how great I am, perhaps one day I will believe it. I’m still waiting patiently for that day.

In my twenties, I believed doubt was something I needed to overcome. That if I worked hard enough, wrote enough, achieved enough and beat my chest enough, I would eventually reach a paradise where I would no longer question myself.

But, I’m slowly realizing that I might have it all backwards.

Perhaps the problem isn’t that I doubt myself. Perhaps the problem is that I’ve spent so much of my life believing I shouldn’t.

In the Sundarbans of India, there are tigers in the forest.

This is a lethal problem for the fishermen and honey collectors who make their living among the mangroves.

Tigers are ambush predators. They prefer to attack from behind. And so, years ago, the villagers developed a peculiar—if not mildly eerie—form of protection. They began wearing masks on the backs of their heads.

Their thinking was simple, but brilliant. If the tigers believed someone was looking directly at them, perhaps they would think twice before attacking. The masks didn’t make the tigers disappear. Nor did they make the forest any less dangerous. But, the masks allowed the villagers to keep working in the presence of something that could very likely kill them.

I’ve always found this to be a gorgeous metaphor for self-doubt. I no longer try to convince myself the tigers aren’t there. Instead, I acknowledge their presence.

I say, “I see you.”

Then I enter the forest.

Godspeed, my friend.

P.S. If you’d like to read the sister piece to this essay, you can do so here.

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