Failure is Awesome
Artistic failure begets career failure begets artistic... and we keep going
Note: I gave this talk in June 2012, to a group of graduating writing students I had worked with for a year as a part of the Attic Institute’s Atheneum program. The illiterate child I mentioned has since learned to read and is about to start college.
The title of this essay comes from an offhand remark I made while speaking at a university in upstate New York. It was 2009, some months after my novel Captain Freedom came out, and I had been invited to speak and perform for a class because I knew one of the creative writing professors. When she introduced me, she explained how we met at a job some ten years earlier, a job I had taken while I was waiting to hear if I had been accepted to medical school.
“And you didn’t get into medical school, I take it,” she said.
“I didn’t,” I admitted to her and her students. “I became a writer instead. There’s a lesson here,” I said, totally thrilled to be paid to lecture to a group of college students even though I had up until that point obtained zero academic accomplishments, “ It’s okay to fail. Failure is awesome.”
The focus of this talk is not specifically about the emotional side of failure, or the failure of your ambitions, though I will visit both of those. Nor is it commercial failure, though that has its place and we cannot avoid it. Commercial success is at least one of the propellers of our work, especially you greedy, greedy poets. What interests me is artistic failure: what happens when the work fails you or you fail the work. I’d like to start by explaining how failure became awesome.
To begin, a quote from The Hitchhiker’s Guide to the Galaxy: “There is an art, it says, or rather, a knack to flying. The knack lies in learning how to throw yourself at the ground and miss.”
A few years after college I applied to some fifteen medical schools. I had spent the requisite hobo years living in California, working as a backpacking guide and a rock climbing instructor. Somehow I convinced myself that a four-year medical residency would be cake compared to living in Yosemite for a summer, or my 8000-mile motorcycle trip from New York to California. Plus I watched ER religiously.
After my intensive study as a vagabond I gained a permanent address and employment, then became an EMT, and worked at the Emergency Department at Oakland Children’s Hospital. At that time I took the required classes I’d blown off in college: a year each of chemistry, organic chemistry, physics, and a semester of biochemistry just for fun. Following this was a brutal six month review for the MCAT exam, then that year of applying, paying for tests and review classes and application fees. A year of waiting, a year of everything on hold, not wanting to unpack my bags and boxes because I had no idea where I’d end up living.
I didn’t get in anywhere. Not a single school invited me for an interview. After spending thousands of dollars and putting my life on hold there was no feedback, no suggestions about improvement, nothing more than form letters in too thin envelopes. The process felt like the close of a Kafka parable: howling at the closed doors of deaf institutions.
This failure was a heartache. Thinking back even thirteen years later I can feel that searing failure in the gut, the reminder of the humiliation that I faced when I’d have to tell everyone I knew that I wasn’t actually going to medical school. That I’d have to tell my mom, who’d been so proud. For many years after she kept a photo on the mantel of me wearing a stethoscope around my neck as I was going into my first hospital shift during EMT training. I’d never failed at anything so stupendously before in front of so many people.
At this point I’d thought that I could get whatever I wanted because I was smart. But being smart doesn’t get you everything. This is an astonishing fact. A similar lesson would be learned several months later in November 2000 by Al Gore.
After a while the disappointment subsided. It took a good six months, and by this point I was living right on the precipice of Y2K and the dot-com bubble burst in New York City: I saw Tom Stoppard debut a new play on Broadway and Max Roach play a free concert at Columbia. Not a bad place to nurse my heartache. If nothing else I learned the word “enantiomeric.”
In the long run this failure of ambition was good and necessary. If as writers we are tasked with plumbing the depths of human emotion and experience, then we should embrace any chance to fail, to feel some level of humiliation, if for no other reason than to become used to the grinding parade of rejections from literary magazines, agents and publishers.
At first when people asked if I would reapply to medical school I said no, it’s too expensive, or no, I’m not ready. Kind of like dating right after a breakup. As time went on I realized the gift I had. At least eight years free! I was out on the streets, released on my own recognizance. Instead of spending those eight years memorizing formulas and cutting open dead people and not sleeping, I would focus on writing.
Eight years later my agent called to tell me that she had sold my book and failure became awesome.
But it was not my first book. Captain Freedom came to be because I was writing the wrong novel. Writing the wrong novel, and learning to survive the experience, is what I mean when I’d like to talk about artistic failure.
The process of becoming a physician is linear: science classes, MCAT, medical school, residency, then medical practice. Why would writing be any different? Short story, novel, agent, book deal.
Fueled by the massive success of my one published short story, which financially netted me all of four contributer copies, I set out to write a novel. Since first novels were always steeped in autobiography, I started writing what would end up being a 400-page manuscript about revolutionary lesbians fighting in Nicaragua in the 1970s.
Write what you know.
I wrote and revised and edited and started over and played with the structure and workshopped. I put my very soul and most of my free time into this book. I submitted it to one literary agent, who rejected it, so I rewrote it some more. I wrote this novel to death.
The novel and I failed one another for a few very good reasons. It was an ambitious project. I didn’t know how to forge an emotional connection to these characters, and I exhausted myself trying to understand them.
My heart was so set on making certain that I treated these ladies with respect, that I wouldn’t fall into typical traps of a man writing about women, that their characters became a little too simple, two-dimensional, anodyne. I wrote generically, fooling myself into thinking that it was because I wrote about a human experience that transcended gender, but in reality I was afraid of committing the sin of not knowing what it’s like to have boobs.
Two years into the project I took a break. It was summer of 2004, and a brand new public radio show called Live Wire Radio asked me to contribute a piece, so I wrote a short story about a superhero who was forced to retire. Like me, he knew about career failure, and was haunted by his past because he didn’t know his father. The character was arrogant and funny and much more like a struggling celebrity than the superheroes I’d read when I was a kid.
In short, I fell in love with this character, and kept writing, even after the initial Live Wire story was done. By the time I performed the six-page excerpt of Captain Freedom at the live show, I had an additional fifty pages, and without meaning to it was quickly becoming my next novel.
You have to ask yourself about your artistic failure: maybe this poem or story or essay or book is not the one true thing. It is not the best poem or story or essay or book that it could be. With short stories and essays and poems the task is slightly easier, if only because of the length. If a short story or essay fails you for whatever reason you can always write another one.
Just because you’ve committed yourself to writing a novel or memoir, doesn’t mean you’ll get it right the first time. The band Pink Floyd released seven albums before they understood their talent enough to create Dark Side of the Moon. Seven albums, including one double album, comprising of a ton of mediocrity. Whether you’re writing short stories or memoir or releasing double albums you have to write a lot of them to do it well.
You have to fail.
At the end of the Atheneum most of you will have complete books. Not complete as in ready for publication, necessarily, but complete as there is a beginning, an ending, and a whole bunch of line breaks in between. And you should be proud, because in writing a book you have accomplished something grand, a feat that nobody can take away from you. Cross that one off your to-do list.
Before you move forward with cycles of revision and editing, it’s important, especially for these newborn books, to ask yourself: do I want to be the author of this one book or the author of books?
When I started as a writer I was very sure that I wanted to be the author of books in general, but as is so often the case I was lying to myself. All my hopes and dreams were tied to getting that one book right.
What I learned from the failure of that first novel was that I didn’t want to be the author of just one book. I wanted to write books, and writing books meant trying, sometimes succeeding, sometimes failing. There a possibly apocryphal story about how many dozens of novels Danielle Steele wrote before publishing her first. When I tortured myself through my first book I thought that this one book had to be The Book, because otherwise, what good was it? I didn’t want to be like Danielle Steele. Who wants to be a beloved, successful author of many books who sells millions of copies?
As soon as I got past the myth of the One Book, when I embraced that failure, I was free to write something that better served my voice and talents.
The process has repeated itself. I have written three novels since Captain Freedom. The first was a comedy about poets, which I’ve been told by publishers is very good but they could not sell a story in which the “The Lovesong of J. Alfred Prufrock” was a pivotal character. Again, I was devastated. You’d think by 2010 I had learned something. It wasn’t that the book had been rejected as unmarketable that was the problem. I wore that as a badge: I’d tried something different.
What bothered me about the poets novel is I felt like I never really got it right. Something was always off, the writing was a struggle and it took me a while to figure it out, but what I learned was this:
The voice was off. I never felt comfortable with it. It was like dancing with a partner where you both assume that you’re the lead: imagine two straight men swing dancing. It’s not a productive fight, and it’s ugly. I’ve tried.
The second thing I learned about the poets book was I didn’t define the book’s comic vocabulary, which I’ve since understood is crucial. But I already knew from my early failures that this book wasn’t the last. So I’ve kept going.
The best thing you can do, coming from an artistic failure is to question the work. Let’s be clear: sometimes no amount of editing can fix it. Once you’ve gotten to that point, that you understand that your failure goes beyond something called “giving up,” you should do a post mortem. Ask the work questions.
From my failures I’ve learned how to avoid traps of plot and point of view. To combine or kill off characters who overpopulate and clog the landscape. I’ve become an avid recycler: past character, plots, settings, rants, monologues and punch lines all have a place. Once they’ve been written they belong out there in the world and they’ll figure out a way to be useful, if only as a bit character or the glimpse of a face in a passing bus. The editing and revision experience has also become easier, occasionally something I enjoy.
You can and should do the same with your successes: I don’t think about Captain Freedom much since the original story is 8 years old, and it’s been consigned to the ninety-nine cent table at Amazon, but every once in a while I think that it could have been more. It could have been bolder, the humor and conceit stretched further. It could have had a plot.
There is nothing wrong with being the author of just one book, rather than many. Perhaps you only have that one story to tell, and now, congratulations, you’ve finished it, never to look back, and you’ve been freed from the shackles of “The Writer.”
But maybe that isn’t it. Perhaps you’ve only failed at that one story. Forget it. Put it in the drawer and write something else.
Some of our perceived failures come from this title. Writer. If I am a writer I should be able to write anything because I am a writer. Have fun roller skateboarding on that Mobius strip.
You were a writer before this program and you will continue to be one after. The certificate you receive doesn’t change that either way. Don’t get so wedded to that one title. Yes, you’re a writer or an author or poet or scrivener or sufferer of graphomania. Wrapping yourself in the cloak of Author has its uses. It isn’t always a black spot. Sometimes it even feels good to be introduced at a party as a writer. Sometimes. You never know how that mantle will change. I’m a humorist or author or novelist, occasionally successful, occasionally dreadful, but I’m also an editor, a teacher, a storyteller and performer.
You are also many other things: friend, lover, parent, child, sibling, reader, harpist or however else you fill your days. I like to spread my failure around: my failures as a writer don’t hold a candle to my failures as a father. My kids don’t think of me as a writer: one of them is a total illiterate. He’s four. Maybe it’s worth writing outside that suffocating label. Spend a day writing as if you were a dancer.
Michael Chabon once said that all his novels were about his failures to make them the books that existed in his head. I think I get what he means. What’s in my head is lit up with emotion and memory and that initiating impulse, the deep why this became a story. A delicious premise, an elevator speech or pitch, three sentences that betray the hard work of the other five thousand sentences. All of this throttles around the neural highway with all five senses offering hints and texture: what comes out can only be ever be words, disappointing words.
I encourage you to fail. Go big. As Samuel Becket wrote in his novella Worstword Ho: Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.
Fail spectacularly. Try something ambitious. Write something you know that you can’t, then try to figure out what went wrong.
That’s what I’ll be doing tonight, in the late hours after we’re all finished, wondering how I failed you, and whatever I might learn from it later.


