Fail Better: How to Succeed at Writing without Really Succeeding

To be a writer is to give up on any hope of attaining perfection.

And that’s actually a good thing.

As a matter of fact, perfection is the wrong goal in the first place. As psychologist Brad Johnson and sociologist David Smith note, “Perfectionism and the desire to excel are not different locations on the same continuum; they are entirely different constructs….In their quest to avoid mistakes, perfectionists stifle their creativity and avoid taking necessary risks.”

Instead of perfectionism, we’ve got to be open to failure. In her book Wild Mind, Natalie Goldberg wrote, “It was important to give myself permission to fail. It is the only way to write. We can’t live up to anyone’s high standards, including our own.” In fact, according to novelist Will Self, “To attempt to write seriously is always, I feel, to fail—the disjunction between my beautifully sonorous, accurate and painfully affecting mental content, and the leaden, halting sentences on the page always seems a dreadful falling short.” And then author Anne Enright: “I have no problem with failure—it is success that makes me sad. Failure is easy. I do it every day, I have been doing it for years. I have thrown out more sentences than I ever kept, I have dumped months of work, I have wasted whole years writing the wrong things for the wrong people. Even when I am pointed the right way and productive and finally published, I am not satisfied by the results. This is not an affectation, failure is what writers do. It is built in.”

But is this just more perfectionism? Do these authors actually have impossibly high standards that they could never possibly meet? No, and here’s why not: These authors live with imperfection. They don’t only dwell in it as they work; they put that “failed” work out there in the world, which is the kind of thing a perfectionist could never do. And these writers fail because they’re trying to make something real, something living and breathing. Nothing alive is perfect. (Consider this: our food and water pipe is immediately next to our _breathing_pipe!)

These authors fail because they would rather have something alive than perfect.

I’ve certainly never done anything perfectly. I’m proud of my work, but I’ve never written anything that came out exactly as I’d have hoped. The closest I came was a story I once wrote called “This Is This Story”—I wrote it in one clean go, and once it was out, I thought, “Yes—that’s basically what I was trying to say.” The only problem is that it was a boring story. It was a very boring story because it did what I wanted it to do, like a machine. I ultimately made sure “This Is This Story” did not end up in my collection The Guy We Didn’t Invite to the Orgy and other stories.

So there’s the paradox: the perfect is boring, what we already know is boring, and the only interesting thing is the living imperfection.

Again, this is a good thing. According to writer David Zahl: “The mistakes in a work of art are not flaws so much as footholds for identification and sympathy.”

And back to Will Self: “This is the paradox for me: in failure alone is there any possibility of success.”

For her part, Natalie Goldberg tries to reframe the concept: “Failure is a hard word for people to take. Use the word kindness then instead. Let yourself be kind. And this kindness comes from an understanding of what it is to be a human being. Have compassion for yourself when you write. There is no failure—just a big field to wander in.”

Well, then, what does wandering look like? According to Grace Paley, “The writer is not some kind of phony historian who runs around answering everyone’s questions with made-up characters tying up loose ends. She is nothing but a questioner.”

As for which questions, David Zahl offers a few: “Failure reframes the questions the artist asks themselves. Instead of what should I create or who should I be, you ask what am I creating? Who am I? If I can’t say what I should say effectively, what do I want to say? These, by the way, are the more difficult questions—and ones which never receive a complete answer. Which is why they’re also more fructifying.”

So, the second step (the first step was to abandon perfectionism) is to ask yourself: what do you care about? (Feel free to pause and do a twenty minute free-write on the question. This article will still be here when you’re done.)

The third step is to risk diving into the unknown. You’re not looking for something easy to solve. In fact, what you’re looking for might not be solvable at all. One of my all-time favorite quotes comes from painter Philip Pearlstein: “I don’t see why painting should get easier. Someone once said that, in a sense, an artist needs a problem he can’t solve. The lucky ones get into a problem that is unsolvable, so they keep going and there’s a growth, evolution.” Or here’s some additional excellent advice from Paley: “Write what you don’t know about what you know.”

(Here you could pause to make a list of all the things you don’t understand about the things you care about.)

Understand that this perspective isn’t cynicism; it’s hope. When you let go of perfectionism, you allow the possibility of something great happening. Or, in the words of Samuel Beckett, from his pretty baffling piece Worstward Ho: “Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

That’s our job: to fail better—more interestingly, more passionately, with more life, getting closer to what we really care about—than we used to fail. That kind of failure is infinitely better than perfection.