Being Comfortable With Failure Makes You A Better Writer

Photo by sydney Rae on Unsplash

In a recent appearance on Marc Maron’s “WTF” podcast, Howie Mandel stated that a big part of his success in show business has to do with “being comfortable with discomfort.” It’s so obvious, sure, but that verbalization of a simple truth really struck a chord with me.

In fact, I’ll take Mandel’s statement a step further (well, maybe it’s just a slight repositioning, but hey, I want to feel like I’m contributing too) and put this out there:

You need to be comfortable with failure if you want to become a better writer. It’s not a matter of if you’ll deal with falling short, it’s a matter of when.

Even though I’m lucky enough to make my living as a scribe, I still deal with failure every single day. Whether it’s a big corporate project or a personal blog post I write for my own amusement (or catharsis), I’m usually in a state of discomfort.

It’s literally my default position.

Despite that, I wouldn’t have it any other way, as far as my process goes. At the end of the day, failure doesn’t slow me down or diminish my writing ability; instead, all it’s done is made me stronger.

Failure is (Unavoidably) Part of the Process

Let’s not kid ourselves: Failing repeatedly isn’t easy.

It’s tough. Tough to accept. Tough to grapple with even when you know it’s true. Maybe toughest of all is knowing that the next failure is coming around the next corner, probably sooner than you think.

At least that’s the way I used to look at it.

Now, having been around the block a few more times creatively, I know that there’s no avoiding those failures. That said, I don’t attach negative connotations of them anymore. Instead, I look at temporary setbacks (and trust me, they never last forever) as a helping hand, like someone stopping to give you directions by the side of the road.

Let’s use the example of having your writing submission rejected. It doesn’t matter what it is or even how good you are at the time of submission — people will say no to you. The vast majority of the time, there’s no malicious intent behind or anything. It’s just a no.

I remember submitting a writing packet to NBC Late Night Writer’s Workshop when I was in the middle of my university undergrad. It was the first of many I sent out to specific shows, other writers and producers in that line of work, and even to agents in both New York and Hollywood.

For the purposes of this article, I went back into an old hard drive and found those old submission packets. I’ve decided to share my first-ever submission packet with everyone reading this.

Not as a point of pride. More because it made my skin crawl.

It’s not good. Not even close. Part of me is embarrassed for the production assistant or intern who had to waste 30 seconds or more of their life reading it.

The important takeaway here is this: Not only did I continue writing comedy-based material after that, but I eventually got paid as a joke writer several years afterward.

Sure, there were plenty more rejections in between. The Beaverton, back when it was just Canada’s version of The Onion and not yet a TV show, told me no three separate times. I did stand-up in front of crowds of 10–12 people who didn’t laugh at a single thing I wrote. Grappling with that necessary failure was incredibly difficult.

Then, after continuing to put in the time and effort, I sold jokes to a few comedians. One particular assignment that comes to mind was a long bit about a female performer getting a wax job. I have no life experience in this area, but my words still ended up as part of a set that, as I stood in the back of the room watching, made a packed room laugh again and again.

That moment made it all worth it. It also put everything into perspective for me. Had I quit before reaching that point, had I given in to the negativity that surrounds failure in most people’s minds, I never would’ve worked those writing muscles hard enough to come up with material that made the cut.

Let that be a lesson to anyone out there who’s sick of being told no: Never, ever stop putting in the work.

History Says Patience is Key to Better Writing

Long-term success as a writer — one that’s built on perseverance and tenacity — is typically hard to come by because, in short, it takes time.

You can’t rush through building that repository of life experience. You can’t skip those steps that involve you grappling with failure, writing hundreds of thousands of words over the course of that process.

In other words, there’s no substitute for putting in the work.

The internet is full of examples of writers that took a long and winding road to get to the point where the masses not only read their work but revered their talent as well.

Stephen King’s “Carrie” was his fourth novel but the first one that ever got picked up and distributed by a publisher. In his brilliant book about the craft, “On Writing,” he revealed that “Carrie” began life as a short story for a magazine. It was his wife who fished the first three pages out of the trash and encouraged him to keep going.

He did. The rest is history.

J.K. Rowling, now one of the best-known and wealthiest writers in the world, considered herself a failure two years before completing the first Harry Potter manuscript. Divorced, on welfare, without prospects, she famously cobbled together bits and parts of the work that made her famous on scraps of paper and coffeehouse napkins.

It paid off.

James Patterson, the first author to sell 1 million eBooks, initially had his first novel rejected by 31 publishers. He’s gone on to write 147 (!) novels since 1976, 114 of which have been New York Times bestsellers.

If that’s not putting in the work.

These are just a few of the most famous examples. Whether it’s writing or another creative field, you’ll find one commonality: Overnight successes are always years, even decades, in the making.

You’re Doing Great — Trust Me

Let me end this blog post with another well-known phrase that has only become truer as I’ve gotten older and written more and more each day:

What doesn’t kill you makes you stronger.

Yes, you’ll struggle. Yes, there will be days where, whether it’s a corporate writing job or the next great (and I mean that sincerely) novel or screenplay you’re working on, that nothing feels like it’s coming together.

I see hate as a strong word that shouldn’t be overused, but I’ll use it anyways. There will be days that you’ll hate most of (if not all of) what you write.

Those days should never stop you though. If anything, those instances of struggle should motivate you to drive over those speed bumps and get to where you need to go. It won’t kill you and will only make you stronger.

Knowing that makes you comfortable with failure. That comfort with the ultimate form of human discomfort, at least psychologically and emotionally, will make you a better writer — one day, even a great writer.

You just have to trust the process. You’re doing great. You will get there. You’ve just got to put in the work. It’s really that easy (but also not easy at all — and I wouldn’t have it any other way).

Digital content specialist with a slight obsession with film.

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