Dare to Fail
What Would You Do if You Didn't Know it Couldn't Be Done?
One of my most treasured possessions is a ceramic jar labeled “mistakes” with the word “mistakes” written upside down.
Perhaps I should be embarrassed to admit this, but I feel that jar perfectly encapsulates my life. Never one to learn from the mistakes of others, I am somewhat prone to rushing head-first into life without bothering to question whether I will succeed or fail. Sometimes, the outcome is as hilarious as it is horrifying:
The time I skied off a mountain
The time I drove a lawnmower into a swimming pool
The time I walked nose-first into a stop sign
In my defense, most of those mistakes have more to do with my lack of coordination than my lack of intelligence. Although I have plenty of mistakes that fall into the latter category as well.
Despite my somewhat frequent errors, I consider myself blessed to have very few regrets in life. My mistakes, while unfortunate, are made with the best of intentions and often in search of joy. Sometimes my efforts meet with failure. Sometimes success. But always, I learn.
And that’s really the point of mistakes anyway, isn’t it? To learn. In fact, I’ve learned far more from my failures than I have from my successes (and I suspect many readers have as well). Sure failures are disappointing, frustrating, and in my case, frequently embarrassing. But they are also attempts at growth, at becoming the best version of ourselves. And I’m okay with that.
My Relationship with Failure
The first story I ever attempted to write was a complete disaster riddled with as many spelling errors as plot holes. My second story went absolutely nowhere. But my third story, my first real attempt at novel-writing where I sat down and did the hard work and put in the long hours, has proven much more successful. Sure I’m currently the only one who’s read it, but unlike my other drafts it doesn’t totally suck, so I consider that a win.
The fact that I’m writing at all originates in my failures. A failed marriage gave me the push I needed to start a new career in teaching, a profession that, despite what people say, I absolutely love. My failures at writing instruction pushed me to reevaluate the way I teach, leading to the publication of my first book, Artfulness: Formula-Free Creative Writing Explorations for Secondary ELA Classes. My failure to sell many copies of that book pushed me to join writing groups and attend conferences, which in turn led me to present at writing groups and conferences. In these communities, which I joined through a series of unfortunate accidents, I’ve thrived. I’ve found community where loneliness once resided. I’ve found confidence where insecurity once reigned. I’ve found courage where fear once lived. It was only by losing myself in a sea of mistakes that I was able to find myself.
"Everything you want is on the other side of fear." ~ Jack Canfield
Success Born of Failure
But here’s the thing. I don’t think my story is all that unique. I suspect that most of us, if we really trace back to the roots of our success, will find a failure that we overcame. Success is rarely born of success. It emerges from chaos and catastrophe, the very things that society tells us to avoid. But I’m not sure that’s always the best advice. I’m not suggesting you should aim for failure—I think an ounce of common sense here and there is a good thing. In fact, paying a little attention to the choices you’re making may be what keeps you from skiing off a mountain, driving into a swimming pool, or walking into a pole. But if fear is preventing you from living your best life, it may be time to reevaluate your relationship with comfort. Sometimes getting uncomfortable is the best thing that can happen to us.
As for me, I’m no longer going to think of failure as the end of a journey. Instead, I’m going to embrace it as one more path toward eventual success. I’m going to dare to fail. I hope, under the right circumstances, you do, too.
Creative Writing Prompt Ahead!
Writing Layover—(Un)Fortunate Failures
Writing Layovers are quick creative writing prompts that can be completed in under twenty minutes. Inspired by my own failures, this Writing Layover challenges you to brainstorm (or better yet, write!) an original narrative focused on failure because misery loves company and I’m tired of skiing off mountains all by my lonesome.
Slippery Slope
It’s the middle of winter and your character has just arrived at their dream vacation: an alpine ski resort. They’ve planned for everything. Snow pants? Check. Goggles? Check. Hand warmers? Check. They’re in great shape, right? But here’s the thing: they’ve never been skiing and their date just ditched them. Are you ready to mess up their trip? Here’s the prompt:
Your intrepid little newbie does not actually want to be there. This was their partner’s bucket list vacay—but their partner peeled off when they spotted someone cuter in the ticket queue. Now your character is all alone. Determined to make the best of a bad situation, they stay on the slopes, watching their former main squeeze shamelessly flirting with someone new. Will they turn things around and come out on top, or will they be snowed out of happiness?
Upgrade Your Ticket
If you enjoyed messing up your character’s life, the (Un)Fortunate Failures post, available for paid subscribers, offers five additional problematic prompts. Why stop at one challenge when you can have six?
Syndication Note
While I don’t generally post duplicate content to Substack, a version of this post first appeared in my LinkedIn Newsletter, which can be found here.