What I Learned from 165 Creative Failures
After a year of creative moonshots and missteps, I discovered everything people don’t tell you about the other “F” word.
In 2017, I set myself up for failure 165 times.
I know this because I kept a detailed “Failure Thread” in Gmail with my friend Alex Jeffries, who also masochistically enjoys documenting creative moonshots and project attempts. Every time either of us applies to a job or pitches an article or submits to a film festival, we add the event to the failure thread as a bullet point. There is no romance or detail or emotion attached to these prospective failures — this is a serious catalogue of every possible effort.
I should note that these are professional failures. They don’t encompass culinary failures (that would be an infinite scroll) or relationship failures (parties skipped, texts missed, emails dropped) or fitness failures (signing up for two marathons and getting injured before both).
No, the failures that I care about documenting are the ideas I dream up, fantasize about, and then try to put into action. They are stories pitched to editors, artist residencies applied for in Minnesota, poems submitted to literary journals. There was that Snapchat short film called Move Over, Mulder, the podcast script I submitted to Austin Film Festival, my application for the theater critic job at The New York Times for which I wrote a play for my cover letter (which was later staged as an actual play called Excuse Me, Mr. Brantley?). There are cold emails to literary agents, copywriter-gig cover letters, and that one online songwriting class I signed up for but never started. They are efforts lusted after, attempted, and abandoned — sometimes all within the same day.
Of course, not every creative kernel turned out to be a failure. Some turned into success. But it’s always easier to remember the ones that got away. Most of the failures stung for a few minutes. A handful bummed me out for days. And a rare one or two are still making me lick my wounds. Failure arrows dig deep.
But you know what?
I’m glad.
I’m glad because I learned more last year than in my last 10 years of writing combined. I learned what it means to want something again — to perfect an application down to every comma, and still not get in. I learned that not getting what you really want is much more powerful than actually getting what you never really wanted at all.
Annoying people like to repeat the Silicon Valley adage to “fail faster, fail better.” (I am one of those annoying people.) No one tells you when you do fail at a creative project it makes you feel unqualified and unworthy. No one tells you that you’ll think about jumping onto a new career track or start sniffing around opportunities you intuitively know are wrong for you, but they’re there — they’re easier — so why not give them a shot? No one tells you that when you fail, you will say to yourself, “Why do I even bother?”
And yet, with a little distance, there are lessons to learn. Surveying the year’s failures can be unpleasant yet invigorating, like taking a shot of apple cider vinegar.
Here are the lessons that slapped me and shook me up last year and are helping me armor up for the next one. Join me on a failure odyssey.
Feeling Like a Genius vs. Feeling Like Garbage
Before attempting something new, I usually vacillate between extreme narcissism and extreme self-loathing. I suspect other creative folks do, too. As helpful as it would be to have an emotional equilibrium, I think this psychotic pendulum is helpful. Yes, I see myself as an award-winning creative genius. And yes, I also see myself as the worst writer in the world who should never type another word. Somehow, it works. You have to maintain self-checks and balances on delusion just as much as you need grandiose goals. When you click “submit” on an application for something you really want, you have to believe that you deserve it. That’s the narcissism. But the anxious run-up and denouement when you don’t get it? Hello, self-loathing!
You Need to Keep Moving
There’s a reason Dwayne “The Rock” Johnson always talks about the wolf scratching at his door. Forget the 96 million Instagram followers, the blockbusters, the fact that he’ll probably be president one day: He knows that a hungry wolf — his competition — can come and bite his head off at any moment. That’s why he’s in the gym at 4:30 a.m., and why he pushes gratitude like it’s a drug. And that’s why you have to have your own wolf. The failure thread was part of mine — always present, always giving chase.
Get Yourself Some Failure-Friendly Friends
When my own projects and daily grind would get a little stagnant, usually the thread would resurface, and Alex would document some new future failure, giving me the essential nudge to do something. To move. To break the stasis. There was zero sense of competition between us — what’s the point of competing with others when you are your most effective and best worst enemy? Usually, seeing his attempts was a boost of motivation, a reminder: Oh, I should find something to fail at today, too. So I would. Because that’s another thing I learned. You can always find a new failure. Always.
Tracking Your Failures Also Means Tracking Your Successes
What doesn’t get monitored doesn’t get done. This is one of those productivity tenets that’s actually true. When I first started freelance writing five years ago, I would wing pitches off into the Internet ether, glad and grateful when I got a response. But then I learned that tracking your efforts provides a backlog of your ambition and a way to measure up against yourself. Why was I pitching consistently in spring of 2016? How did I juggle directing a play, editing for a website, and writing freelance pieces last winter? I have no idea! But the reminder of these exhaustive efforts — ones that worked and others that didn’t — makes me think, If I did it once, why can’t I do it again?
Trying More Actually Gets You More
Sometimes friends will say to me, “Wow, you do a lot of stuff!” which is maybe a compliment or maybe a sign that my brain is splintered into too many pieces or maybe both. But I always want to explain what they see is perhaps 5% of my actual attempts. Sure, I launched a daily newsletter and went to the Bahamas to write about Suze Orman’s blissful life in retirement, but I was also ignored or ghosted by dozens of editors, rejected for loads of prestigious fellowships and workshops, and wrote a handful of New Yorker Shouts & Murmurs columns on spec, which were all kindly denied. (If anyone wants to read “To Discover Everything You’ve Ever Wanted in Life, Please Click Link in Bio” or “Now Accepting Applications for Adulting School,” let me know!) Little failures hurt a lot less when you’ve got eggs in a bunch of baskets.
Planning’s Not for Losers
Although last year didn’t go exactly as I planned (or, it’s safe to say, as anyone planned), there’s a lesson in that: I didn’t plan enough. Rather than pick a few tentpole goals and attack them with precision, I sprinted to short-term deadlines and hoped for miracles. This is better than doing nothing and hoping for everything; I understand that. But last-minute surges are a far less tactical, and far less effective, strategy than careful plotting. Now I know.
Quit What Isn’t Working
Fail me once, shame on you. Fail me twice, shame on me. Fail me three times, just take away my computer because clearly I’m hopeless and have learned nothing. That’s what I figured out after writing my first feature film about a self-help guru who returns home after her empire collapses. I was so pleased that I wrote 99 pages of something that I kept submitting it for feedback from fellowships or festivals. But I never actually incorporated any of the useful advice I received; instead, I was hunting and gathering and waiting for someone to tell me it was perfect, knowing full well it wasn’t. I would have been better served by either improving the script, or putting it away and returning to it later. My advice: Abort all your half-pregnant executions. They’re taking up valuable time and energy.
Stop Waiting for Permission
Quite a few of my failures are carbon copies — applying to competitions or festivals, then waiting months to hear back about results. Feedback is valuable, and necessary, to improve your craft. But that’s also a convenient cover-up for the real reason I love submissions. Submitting gives you the illusion of progress while you wait for permission. What I really wanted was someone else’s stamp of approval — a shiny gold star telling me I was Good Enough. But you know what happens when you wait around for someone to tell you you’re good enough? Nothing. Literally nothing. You waste months waiting. Not working. Waiting. And that is dead time you will never get back.
Collaborations Can Fail, Too
The other big lesson from last year was about collaboration — namely, my realization that I craved the specific lightning bolt of artistic betterment that happens when a group of excited professionals get together in a room to create a play (or magazine or website or new app, anything that takes more than one brain). Ideas morph, creativity mounts, and as a group, you create something from nothing. But the occasions I thought would grant me that free-flowing collaboration ended with me stuck in a one-sided creative silo, shouting, “Don’t you wanna work together? Please! Can anyone hear me?!” If you wait for someone to hear you, you’ll grow bitter with their silence.
Every Failure Is a Brick
I took an online playwriting class last year. I failed at that. I got bogged down and didn’t complete my assignments. But what I did finish gave me the shell of a story to submit to a play development series. That was another failure: I was a finalist but didn’t make the cut. But that got me to finish the first draft of a full-length play, which I now have sitting on my desktop and will work on next. What I’m trying to say is every micro failure is a brick. You may be standing too close to see what you’re building, but as long as you keep laying bricks, you will build something.
So that’s what I learned last year about failure, and what I hope to remember throughout much of next year. Don’t give up control, don’t ask for permission, don’t sit on your ideas, and maybe don’t worry so much. Above all, just do. Happy 2018. Failure awaits.
Magenta is a publication of Huge.
