The Naked Truth About New Challenges, or, That Time I Made a Dumb Bet

Many years ago, I made what would politely be labeled an ill-advised bet. I was at a college party—one of the few I’d ever attended—and I seem to have forgotten two important points: 1. Beer Pong success requires talent and/or practice, and 2. My luck is abysmal. I always lose a bet. Always.

The payout, if I won, was a pittance. If I lost… sorry, when I lost, I was to strip naked, wait as party goers (25 people or so) were called to attention, and then jog three laps around the room. I was a stupid, stupid man.

My opponent dropped their first three balls into the cups, and I was immediately grateful for the penalty of beer that came with each one. At least some part of me would be numb to the cold air and cat calls. Still, with each PLUNK! I regretted the life decisions that led to that point. All of my most unflattering parts were about to go on full display. The hairy places! Potential butt-pimples! My incredible lack of musculature…

And yet the feeling wasn’t new. Because believe it or not, writing feels a lot like that. Well, not writing per se. Writing is taking a shower alone behind a locked door. Submitting that story, however, is dropping your pants in public and acknowledging that yes, this will be remembered. 

When it comes to writing, size matters. Publishing a blog, for instance, often feels like putting a few prominent blemishes on display. Short stories are more akin to the aforementioned naked jaunt of shame. And a novel? Well now it’s your soul that’s been revealed. You are as exposed as you can be—more naked than naked, let’s say. Simply writing a first draft feels like confirmation of your inadequacies. I can’t begin to imagine how it will feel when it comes time to submit!

This is why I’ve begun to challenge myself in new ways. No, I haven’t become a nudist—I’ve been entering short story contests. Big ones. These average roughly 1,700 entrants from around the world. Each contest is made up of multiple rounds and a 48-hour time limit. The prompt, a nasty requirement that is randomly generated and yet seemingly designed to deflate all hope of success, is provided only when the clock starts ticking.

These aren’t quite like my ill-fated beer pong bet. The payoff is better: money, publishing, a notch on your writer’s belt. Losing simply means your entry fee becomes someone’s paycheck. Either way, you still feel naked. Like a plucked chicken. On a stage. With a ruler in your hand. You wonder if you can measure up.

And yet, this is a fantastic learning experience. I care not about taking the prize. I do it to push myself, to learn, and to adapt to the feel of open air on my nethers. After all, if my dreams are to become reality, I will spend the rest of my life showing off my junk to strangers, and—wait—

You do understand that this is an allegory, right? I don’t go showing my… you knows… to just anyone. I’m a reasonable, law-abiding, non-exhibitionist minded person of character, and… Oh, you DO know this is a metaphor?

Okay then. I just didn’t want you going around assuming that I… well… let’s  just get to wrapping this up, shall we?

I lost the bet. I don’t remember the specifics—whether I made a good showing or I missed every shot. What I do remember, what I cannot forget, is the moment that I dropped my drawers. All eyes, even if controlled by only temporary curiosity, studied the lay of my land. Oh my god, he went through with it? I was on full display—unflattering bits and all.

Rather than jog, I strutted around the table like a peacock displaying his feathers. I smiled for pictures. I dispensed high-fives. I was the emperor in new clothes, embarrassed, but wiser. Well, a little wiser, anyway. And those flaws I was so worried about? Eh, who cares? We all have flaws. I just happened to be parading mine—boldly.

And as brave as a writer.

Now, I’d like to hit you with a parting thought, a question to help clear your mind of the horrific images I’ve painted onto the walls of your brain, it is this: Are you naked right now? Perhaps you should be.

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