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What Is the Worst Thing You've Ever Made?

Jen Doll speaks to a bunch of different creative types about what they've all learned from being bad at what they now do well.
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(Photo: triggerhappy09/Flickr)

(Photo: triggerhappy09/Flickr)

I, like many a writer, have an unpublished novel just sitting in a file on my computer. Its working title is With this Ring, and it’s about a con artist who steals cars via his car wash business/scheme. He’s conned by another con artist (the personal assistant of an aging starlet) into marriage; she takes off soon after, setting off a madcap cross-country journey and a bunch of crazy consequences. The plot of this book—there’s an Elvis impersonator involved—still makes me giggle in its utter wackiness, but I can admit that my 300-and-some pages had a few issues. For example, there’s a coke-addled lemon farmer who rides a giant tortoise as a major character. So, you know. It’s weird. While I got a few agents to look at it back in the '00s, no one bit, and I put it away, mostly forgot about it, and worked on other things, including my memoir, which did get published this May, Save the Date: The Occasional Mortifications of a Serial Wedding Guest.

"Ten years into my 'career' in 'show business' I've never had to do anything more degrading than trying to use a cake to shield my penis from the eyes of an audience that was waiting for a crowd to perform."

Only recently did I think back to that old novel that had never gone anywhere, and how a wedding—consider the title!—was a key part of it, too. Clearly I’d been thinking about this topic in different ways for years, fictional and factual, and even though I consider that first book a kind of creative “worst,” which is to say it never saw the light of publishing day, I also have a fondness for it. It taught me that I can commit to the labor of writing, page after page, sticking to it and doing it. It gave me a sense of how characters, no matter how kooky, might be developed, and it freed me to write creatively, maybe too creatively, in a way that I hadn’t done before. It’s not my best work, but as a worst, it’s a thing of great value.

All creative people wrestle with “worsts”—they’re part of the business. They bring shame, of course. It feels terrible to work on something for months, years, and never have it acknowledged, not to mention never have it make any money. (Our job as writers and creative folks is to sell things, after all). It feels similarly awful to make a decision you fear will change your career in a way you can’t recover from. But in whatever form a worst may take, almost always, it has a way of providing a lesson, and almost always those lessons lead us to something better. I talked to nine creative people about what they’ve learned by doing badly.

Porochista Khakpour, author of The Last Illusion, out now from Bloomsbury

I got a very hot, very big deal agent (I've had three; the second one retired which is why I'm on my third) as my first agent. He was everyone's top choice—a handsome, smart, stylish, edgy, dream New York agent. He loved the idea of my first novel but wanted edits. I said, sure, and there was a whole summer where I was supposed to be working on them.

Then one of my first personal essays came out and became unexpectedly very popular; I had cleverly mentioned I had a novel I was working on in my bio, and so an editor at a major publishing house wrote me dying to see it. So I wrote my agent. Well, I hear nothing. I tried to stall this editor but she seemed in a real rush to read my work. So I wrote my agent again. Still nothing. At some point, I sent my manuscript without him approving that move. Eventually he responded and I told him. He was upset. He told me it was far from ready. He was insulted.

And you know what? I didn't apologize; I didn't feel bad; I dumped him. And while it took me another half a year to find another agent (it actually didn't work out with that publishing house—oh well!), it was the best thing that could have happened. I was concerned at first that I'd walked out on this major blessing. Well, in years to come, several of the other authors he repped became friends of mine and they all had terrible experiences with him and eventually all left him. So fuck that guy.

Sometimes being hotheaded and doing it your own way and walking out on all the hot shit might be the right thing to do. Pretty sure a ton of my writer friends would have tried to stop me at that point. Oh, that's another thing: Don't ask for advice too much. Go with you, as gritty as that might be at times.

Lev Grossman, author of the upcoming The Magician’s Land, the conclusion to his Magician’s trilogy, out in August from Viking

My worst work: There's a hell of a lot to choose from. I wrote pretty constantly throughout my teens and twenties, lots and lots of short stories, dozens of them, and I hardly published any of it, because none of it was very good. The worst was probably when I was in my fake-Donald Barthelme period, when I wrote these stories that had no plots and were just these archly comic snippets that went nowhere. Yeah—nobody else liked them either.

I definitely learned an important lesson from that, which is that I'm not an avant-gardist. I thought being a sophisticated 21st-century writer was about breaking stories apart and looking at the shards. And maybe it is, but that's not me. I'm about building stories up. I like telling stories. But I couldn't admit that before I tried going down the other path.

Jami Attenberg, author of The Middlesteins, out in paperback from Grand Central

I've thrown away two novels I've written, one because it covered the exact same themes as the previous two novels I'd published, and one because it didn't feel like a step forward, it felt small and odd, almost like a sidestep. I am pretty sure they weren't the worst books ever written, and it is hard for me to say out loud that they were the worst books I've written, but they definitely were not my best. But in both cases they served a purpose and got me to the next place in my writing.

With the first book I threw away, after I finished it, I recognized I needed to start addressing different themes and perspectives in my writing. So then my next book was dramatically different, written from third person as opposed to first, and it was a family drama as opposed to a relationship drama.

With the second book I discarded, I ended up trying different things in terms of structure and action, which I might have been hesitant to try in the space of a different book. In the novel that followed, I ended up using the techniques I practiced. I realize now I needed to try them out first in the book I discarded for them to work the way they did in the second book.

Rembert Browne, writer for Grantland

My clearest and most obvious "worst" pops into my head multiple times a week, typically whenever I think about a student-loan repayment, which is often. I went to graduate school, failed a class, and then self-sabotaged the rest, followed by dropping out. And it was the best thing that's every happened to me, professionally.

Within months of being at Columbia for an Urban Planning master's, I could tell it might have been a mistake. I was fine and could've probably figured out a way to graduate, but I wasn't flourishing like my classmates. And, more importantly (to me), I wasn't happy. And then, toward the end of my first of two years, I failed economics. Which meant I had to re-take economics the following year, with all the first-year students.

As a guy with a ton of intellectual pride, the idea of being Billy Madison was not appealing. So I kind of stopped going to that class. And then some of my other classes. And when I went, I worked on my blog, something I started as a response to being so unhappy in graduate school. I needed an outlet, writing had always been my outlet, and who knows—maybe it could also be my out.

During that third of four semesters, my grades were tanking near that luxurious "Academic Probation" level, but I had gotten a few pieces up at this new website, Grantland. By October, class was just a place with fast Wi-Fi to make Internet about sports and pop culture, and by November I was home for Thanksgiving, telling my mom I was dropping out of graduate school to go write about music and stuff for a website that was five months old.

And none of this would have happened had I even approached being a good student. There's a lesson in there, somewhere.

Jennifer Sky, former model and actress, writer, and models’ rights activist

As child, growing up in the swamps of Florida, I was fascinated by the images I saw in fashion magazines. The girls in those pictures seemed to live perfect, glamorous lives. To a dyslexic, outcast girl like me, nothing could have seemed further from my small-town existence. I wanted to escape into the fairytale lands magazines created. At age 14, I won a modeling contest with Seventeen, and my mom and I were flown out to Los Angeles for my first photo shoot. While the hive-like atmosphere of the shoot was exciting, it was also terrifying. Right away I was asked to change in front of a room full of adults without any thought for my age or gender.

But the biggest shock I found was how hard we all had to work to get one usable photo. Modeling is a job, and a very athletic job at that. Imagine this: running up a sand dune, in stilettos, wearing a fur coat, in the middle of the Mojave Desert on a 100-degree day, and shooting that “story” upwards of 10,000 times in order to get one image. Now think about how many selfies you need to take just to get that perfectly puckered profile photo. It’s hard work to make a good photo. As a 14-year-old in the early '90s, this was a huge surprise to me. My expectations when I started my career were the same as all day-dreamy teens: fame, fortune, jet setting, dripping in diamonds.

The truth I found is that, yes, fashion is an extraordinary world and being a fashion model is a wonderful opportunity— by the age of 17, I’d traveled to Japan, Italy, France, and Mexico, and lived in both Miami and New York—but I was also neglected, desperately lonely, overworked, and abused.

The models we notice and hear of the most often are the famous ones. The top one percent of any business are the success stories. Some supermodels have made millions, but they are an elite few. It is the models in your Sunday flyers and those that work in small markets across the globe, places like Jakarta, Seoul, Bangkok, Seattle; these are the middle-class models who keep the industry fed. They are most often underage and from underprivileged backgrounds, having dropped out of high school to chase the fashion seasons as they roll out across the world. They live on food allowances, in overpriced, agency-managed apartments, which they are then indentured into paying off. They can fall off the face of the map with no one noticing. They can simply never come home.

It was this world I found myself in when I was offered an $8,000 contract to work for two months in Japan. I was 15. The human trafficking elements of fashion were all around me; party promoters and shady modeling agencies making their living off of young girls, both on and off the set. Models are routinely set to clubs and on dates with wealthy businessmen and agencies profit. This happened to me in almost every market I visited. Everyone was a vampire.

My experiences in fashion changed the course of my life. Twenty years later, while I am still dealing with the psychological fallout, I am doing what I can to change the way fashion treats its young workers. This past fall, New York State passed the Child Model Law, granting protections for minors working as models in the fashion industry. Protections such as school-night curfews and on-set hour limits, chaperones, tutors, and mandatory financial trusts are now law. I can’t say that knowing what I know today I would do it all over again, but I am happy to know that I can help to protect others from suffering similar conditions.

Philipp Meyer, author of The Son, out in paperback from Ecco

My worst work was my first unpublished novel. It was very long, but also managed to be very bad. Basically 600 pages of incoherent nonsense. A very typical first novel written by a new novelist infatuated with the sound of his own voice. Kind of like a child learning to talk. Hey look at these fucking awesome sounds I'm making, you fuckers!

Though it's likely that particular novel is in a tie for bad-ness with all the short stories I was writing at that time. We're talking years zero to five of me considering myself a writer. Years six to 10 were an improvement. My second unpublished novel was only mediocre, though realistically probably good enough to be published, but thankfully I had no connections, so instead of being published it was turned down by like 100 different agents.

I have a feeling those things saved me, artistically. I figured out how to be an artist in private. During Years 10 to 15, which was the time my work began to see the light of day (a few short stories, followed by my third novel, American Rust, a.k.a. my first published novel), I had actually become an artist. I'd crossed the border from apprentice to practitioner. And of course, I kept getting better. Those first published stories were good, I still stand by them, and one is still anthologized a bit, but when I wrote them I only knew how to work in one voice and tell one type of story. Which was an enormous improvement from not understanding how to work in any voices and not knowing the difference between what I wanted to be true about my work and what actually was true. American Rust, my first published novel, was actually my first mature work. I'll stand by it 'til I die. Though of course I wouldn't write it again, not in that exact same way.

Making mistakes is not necessary to the creative process. It is the creative process. This cannot be overstated. American Rust was 375 published pages, but I know I wrote over 3,000 pages for that book; I rewrote certain sections a hundred times. The Son (second published novel) was about 600 published pages; I actually stopped keeping track of all the pages I wrote, because by then I was at peace with the idea that all those mistakes and dead ends are crucial to finding the final work, but I'd guess I wrote, hmmm, I dunno, at least 6,000 pages? At least?

It's basically normal for you to think that because you are smart and literate and are good at writing essays for English classes, you are a small step away from making art—I certainly thought this. And, probably, this delusion is crucial. You have to grossly overestimate your abilities at first, or you will never, ever keep going. You only improve by doing it. It is identical to a sport in that regard. You cannot think or study or mentate your way into becoming a good artist anymore than you can think your way into becoming a good athlete. It is all, all, all practice.

The difference between a smart, literate 25-year-old who has never written a novel and the version of that person who can write a successful novel, who can actually make art, is almost exactly the same as the difference between a kid playing little league and that same kid getting signed by the Yankees. Making art has no relevance to anything else you do in life and it can't be studied, it has to be learned, on the job training, like anything else in life, by doing and failing and doing and failing, again and again. But a few hundred million repetitions later, boom, you're an artist....

Deborah Harkness, author of The Book of Life, the conclusion to the All Souls trilogy, out in July from Viking

I imagine that every author has a packet of cringe-inducing literary efforts from their childhood. I'm no exception. Mine include a terrible 4th-grade attempt to emulate Louis May Alcott's works. I mashed together Little Women, Eight Cousins, and A Rose in Bloom and ended up constructing a family with eight sisters all of whom were named after flowers. I was apparently so exhausted after deciding on which sister would be named Daisy and which Pansy that I didn't get much further!

Daniel Fishel, illustrator

When you move on from your high school art program to an art school you learn very quickly that you are no longer the cream of the crop of your domain. Other people are way better than you, and you are no longer the art star that shines the brightest. You spend the next couple of years smoothing out your craft so that by the time you graduate art school, you'll be able to start working right away. Or at least that's the hope.

For myself, it seemed like a career in illustration was possible right away. I had gotten recognized into three of the four biggest competitions in illustration: The Society of Illustrators, American Illustration, and 3x3 magazine. I’d even gotten an acceptance letter to study at the School of Visual Arts, which meant I was moving to New York City. So I printed up a hundred postcards in May 2009 and mailed them to all of my dream art directors. I was proud of the cards I printed and patiently awaited for my full cover illustration or even a series of spot illustrations. A month or two went by and I heard nothing. In July 2009 I made a new postcard and mailed it out. No replies. I moved to New York City in August and mailed out another set of postcards in September 2009, and still, nothing. As I was writing and stamping another postcard in November, I got an email from my first editorial client. It took six months to get that first email.

The big lesson that took me almost five years to learn is that nothing is immediate in the creative field. I didn't really start living off of my work 100 percent until two years after my first postcard. You work hard, you improve, you do a good job, and more people will hire you for the kind of work that you'd like to do. It just takes time to get there.

Josh Gondelman, comedian, writer, and Web producer for Last Week TonightWith John Oliver

I'd been doing comedy just over a year when I agreed to perform in the Naked Comedy Show in Cambridge, Massachusetts. The show was exactly what it sounds like. Comedy. Performed. While naked. I thought taking the gig would help me overcome any lingering anxieties I had about speaking in front of people. My set went about as well as it could have, given my high levels of inexperience and frontal nudity. After I performed, the host asked me to help the following comedian (a naked female clown) set up several props around the stage.

"Sure," I said. "Just let me grab my shorts."

"I'd rather you didn't," the host replied.

So at 20 years old, I crouched naked on the stage of a black box theater, setting up a cake, a place setting, and an easel for a clown.

"How did my life come to this?" I thought. "I was supposed to write novels."

I did feel more comfortable onstage when fully clothed after that night, but really, what I gained was perspective. Ten years into my "career" in "show business" I've never had to do anything more degrading than trying to use a cake to shield my penis from the eyes of an audience that was waiting for a crowd to perform.

And for that I'm grateful every day.