The Art of Cringe: How Regret Drives Us

A long while ago, I made a YouTube video. It follows a college student attending a baking school, bombarded by dinosaurs—oh, and a romance. I spent weeks of my life learning how to edit (poorly) in Adobe Premiere, I bought a used Blue Yeti microphone, and I got to work. My leg shook while my apartment Wi-Fi struggled to upload the disaster, and when it finished, I shared it with everyone I knew.

I got twelve views and one like. "My debut has become one of the most embarrassing things I've shared," I thought.

There was a period where I posted nothing online, fearing those twelve viewers, but that was short-lived. I'd moved on before I realized, letting the cringe fade into the back of my mind. The memory resurfaces in moments like this—moments where I'm proud. My short film was stupid and awkward and I showed it to one too many crushes, but alas. I learned, and I moved on.

I'm not sure what enabled this, but I've identified what helped me the most: I had other horrendous, vile, stupid videos to release. After that second one, I ran out of ideas. Had I pinned my entire success—my career—on one video, I never would've released it. My college bakers would sit in an over-edited, scrapped, and re-created (twice) project file, remaining there for years until I'd decide one of two things: this is my big hit; or, this is garbage.

Once again the video would get, oh, sixteen views? I'd cringe myself into my grave. I would've preferred to throw away my dreams to live in delusion, thinking, "This is the best creation in the world, but I can't share my masterpiece because no one would appreciate it..."

If you've created or pursued something, you understand. Think about a crush. The one you could've talked to. You were ready—had the night been perfect; otherwise, you'd be like my YouTube video. Weeks of crushing, a few supportive friends, and a cringe moment haunting you eternally.

There is no point in risking your heart, but what if you had? Now you get to live with your indifference, a failure to haunt you to your grave.

But that’s just it—indifference is its own form of failure. The real challenge is learning to lean into the embarrassment. It's an art, making mistakes. Living with them, yet persevering through the fear and regret they bring. This is the art of cringe.

Let's review your broken heart. Say you got the courage to ask that special someone out, but your breath smelled like moldy cheese and you didn't know until fifteen minutes too late. Now they're gone and the love of your life is gone forever, but you'll never forget to brush your teeth.

You find another special someone and this one accepts your date! You brush your teeth and race to the diner—only two minutes late, not bad—and things go well! Later you see a text: I'm sorry, but I don't think this will work. I have no clue if I'm interested in marrying you or if we'd be good with kids because we just met and I'm just after a good time.

Ouch. So you came on too strong. You were also after a good time. Next time, you'll focus on that. Now, how to flirt...

Okay, date number three wasn't after a good time—and their breath was vile. You meet a fourth and a fifth. By the sixth, you know what you're after, and who you'd like to be for this person. And the sixth? They stay.

Dating isn't something we afford to give up, so we learn the art of cringe through it. For some of us, we're compelled by an art form that forces us through this disastrous process. Some of us never make it out. Failed businesses, scratched novels, or smudged paintings. We'll see an acceptable failure, something minuscule to others. In reality, nothing is perfect. We idolize perfection, yet nothing has been created perfectly. Not once. Think you have an example? Ask the creator, and they'll list the flaws.

You'll be stuck forever if you don't accept your mistakes. You have to move on. The cringe means you're learning. You've found the flaw and you can see it, too. Isn't that the best part? You've learned what you did wrong, and you'll do better the next time. Find that wall and get climbing. You may fall, but you'll grow stronger with each attempt.

In some ways, I found my wall, the biggest hurdle to overcome to reach the starting line. Not the finish line, no. I've sat on a drafted novel for years of my life, carving and biting away until I could tolerate the plot. Even so, I avoid that hurdle. Why? I've spent years of my life there, labeling that novel a part of my identity as a writer. I'm trapped now. I get rejected or reach that twelve views mark, I'll have nowhere to fall but face-first into a pile of mud. Had I let myself fail years ago, I believe I'd have moved on with a better writing process with a second novel already written.

Alas, the art of cringe has eluded me here. Too much pride, too much hope. I don't think I'd feel that way if I'd let myself fail more often earlier on. Maybe that's why I write here: a fresh slate for me to fail peacefully.

Writing Exercise

Write from the perspective of someone who failed. Give them some breathing room after the event. It was a year ago, maybe a month ago, and now they're trying it again. This could be anything: a kid learning to ride a bike, a painter rejected by their local café, a faulted driver overcoming a car accident... Better yet, make the story about you. Write about one of your aspirations, after failing it once already.

We understand failure and its value. It's time to focus on the hidden drive that it brings.

Share your cringe moments with the crow. Trust me, it feels good to get it off your chest.