The Pit of Discomfiture

Or, where creatives fall into despair


The last time I fell into the Pit was a week ago.

It happened because I got Internet-lost, which is to say I was following links across the web indiscriminately when I stumbled across an old haunt and inspiration like an aurora borealis struck me: I used to draw! And I wasn’t half bad! So why don’t I make like Monet, bust out the trusty ol’ Wacom, and whip up a nice little piece of art? With a few loose strokes, I could paint a sunset masterpiece, some golden fields, a capybara or two

This is how it starts. Your eye sees something that moves you, so your hand yearns to create: a photograph you cannot put into words, a passage of pure poetry, a finely-tuned composition, an insouciantly tucked shirt, a stroke or two of wisdom, a speech that ricochets in your ribcage long after your eardrums have stopped vibrating.

See, the world holds things of such beauty that once you are made aware of them, you think—foolishly, perhaps—that maybe it is your calling to create such things as well. You think—stupidly, of course—that because you picked up the pen or the instrument or the handbook and because you are bathed in the light of inspiration, the place you want to get to will be easy. You can see the destination clearly, after all, and it does not seem so far away.

A few steps in, you realize how wrong you are. The road beneath you crumbles, and suddenly you fall into the Pit of Discomfiture.


dis·com·fi·ture [dis-kuhm-fi-cher] noun
1. disconcertion; confusion; embarrassment.
2. frustration of hopes or plans.

The Pit of Discomfiture is a place with which I am well acquainted, having spent a good number of years here on the way to every conceivable destination, all the while pretending I were someplace more pleasant, like on a sandy beach or up along a mountain ridge, anywhere other than this dank, dark pit of self-loathing.

I was in the Pit weeks after designer became a part of my professional title and, having little clue what that meant, I embarked on an hours-long argument with a fellow designer about the merits of Windows versus MacOS.

(I was arguing on the side of Windows.)

I was in the Pit all those times I sat down to design, and I could grasp the shape of what I wanted in my head—I’d recognize it in an instant if it were in front of me—and yet my hands were clumsy, the thing on the screen was a mockery, a poor imitation of what could be so so so much better. If I only knew how.

I was in the Pit when I sat down for my first portfolio review and upon being presented screen upon screen of other people’s designs, realized that I had trouble distinguishing good work from great work because my taste wasn’t well-developed enough (but of course, how could I admit that and ask for help? A designer’s entire job is to have good taste).

I was in the Pit when I first sat down with the intention to blog, and every first sentence felt bland or bloated or simply false, and organizing my thoughts in a coherent manner felt like sorting through a dumpster full of tangled Christmas lights.

These things I can admit freely now, as enough time and hard-won boss battles have passed. It’s easy to be honest when you’re talking about yourself as a character from a previous era.

But don’t misunderstand.

When you are currently stuck in the Pit, it sucks. And it is extraordinarily difficult to admit, even to yourself. You either delude yourself into thinking nothing is wrong with you (it’s the environment conspiring against you—the shitty weather, your boss, that meeting, the whole stinkin’ culture of this place), or everything is wrong with you (the way you look and talk and think and act—the very atoms that make up your being, in fact—all of it is wrong.)

The Pit is a personal obstacle, but many aspects of it are universal. The walls are grey. The air is uncertain. You can barely see your hands in front of your face, and you will not know where you are going.

Also: everything you do or make will be shitty, and you will hate pretty much all of it.


There are—and have only ever been—two ways out of the Pit.

The first is to forego the whole adventure and take the elevator back to the start. Yes, it’s as easy as it sounds. A single command, and you’ll be sitting on a cushion of clouds, zipping your way out of the darkness and into the open blue sky. Why deal with all the frustration of traveling? Aurorae borealis are stupid, anyway.

The second way out of the Pit is to wander through the dankness, tripping and stumbling in the dark until your feet strike something solid—a step, a slight elevation to push off of until you are just a few inches higher than you were. And then you do it again—trip and stumble and wander until you find the next step. And the next. And the next.

There is a path, harrowing and barely visible, but it is there. Leading from the Pit up to that place you saw from a distance when your heart was swollen full of inspiration.

This path is hard. The darkness does not clear for miles. Your ego will take a bruising on those jagged walls. You may get lost for weeks or months or even years. And everything you produce while on this path will be garbage. You may even be gripped by the ugly vice of jealousy when you see others bound past you on some alternate road high above, one that seems well-lit and smooth and lined with daffodils.

But at the end, know that there is nothing like it. To have gone through the Pit, to have climbed it rock by painstaking rock and emerged capable of creating the kind of work that pleases you, the kind that filled you with inspiration in the first place—nobody ever regrets the journey.

It just doesn’t come easy. For anyone I’ve ever known.


Naturally, we celebrate the photo-perfect finish. And why not? Nothing beats the view from the top, with the aurora borealis in dazzling effect. We like achievement. We like to hear about how winners win.

The stories from the Pit tend to be under-rug swept.

You might recommend or share or an article I’ve written, but you probably don’t know about the four unpublished novels sitting on my hard drive, two of them truly terrible, written over the course of 4 years.

You might hear me speak as an “expert” on some subject matter, but you probably don’t know all the ways I’ve cut my teeth on the different flavors of wrong—trusting intuition too much, or reading too many fortunes out of cold facts and data dashboards, or misreading my gut, or doubting I had one in the first place.

For every Pit I’ve climbed out of, there are just as many I’ve failed to surmount.

This is, I think, also true for anyone I’ve ever known.


Do you want to know what happened with the sunset I wanted to paint?

I laid down a few strokes and put together a color palette. I started sketching. Purples were laid down first, then oranges, then yellows.

The drawing looked awful, but I pressed on. Greens and blues to blend the sky. Mustard to outline the shape of the fields.

It did not take shape the way I imagined it. The landscape looked like scribbles, not stalks. The purple I had meant to suggest distant mountains looked like ink blots.

Half an hour later, things were no better. I could no longer see the end, how this mess could transform into something I was even remotely satisfied with. The process wasn’t fun or liberating. I grew more and more frustrated with myself.

I couldn’t bear it in the Pit of Discomfiture. So I took the elevator back and gave up.


In all of your journeys, I hope the roads are smooth and lined with daffodils and the destination is always clear in front of you.

But if you do happen to find yourself in the Pit of Discomfiture, know that you aren’t alone. Carry on. Just keep going.

At the end of it, I hope that the aurora borealis is as lovely as you imagined, and that the things you make when you get there will become the northern lights of somebody else’s dreams.

Photo by Studiolit