Online writing challenges are everywhere these days, and freelance writers should enroll and submit their outstanding pieces to as many creative content competitions as they possibly can.

However, with all the hype, you will need to buckle up and realize you are about to walk on the shoulders of giants. When entering a competition, you’re no longer writing for your drawer, your writing will have expert eyes on it, and you should be ready to deal with feelings of failure and defeat.

I’m writings this piece because at some point I was tired of losing writing competitions. I’ve been there, seen that, and moved on. These words come straight from personal experience and fruitful brainstorming with other writers. Thus, I hope my findings may help you on your journey.

5 Reasons to Join a Writing Challenge

Hereunder, I’ve outlined in hindsight a series of arguments in favor of entering writing challenges.

Challenges help you get out of your comfort zone because there will be instructions and a topic to follow. You get to stretch those lazy writing muscles to meet the deadline as you go up against some of the best voices out there.
Prompts improve writing pace by promoting energy bursts. Your track record will improve in time, and you will notice you’ve bulked up your endurance as a writer.
Joining new challenges enhances your creativity as you get to listen to new voices from within yourself that otherwise would remain silent forever. For instance, if you are a long-form fiction writer, why don’t you join a poetry competition. Who knows, maybe you’ll finally connect with your inner Shakesperean surrogate.
You get to learn from others. Writing for challenges will develop connections and build a sense of community.
Last but not least, you can win thousands of dollars, and that’s something you don’t want to miss.

That last point on my list is the trigger for this piece. I’m by heart an introvert struggling against my true self towards unleashing my voice into the world. Hence, I’ve only recently challenged myself to take part in writing competitions.

I’ve joined thirty online challenges starting from November 2020, and I’ve never been close to winning. I also never made it to the runner-up position or third place in any competition.

At this point, the low self-esteem may start to kick in; hence I’ve recently been debating and brainstorming with some of my closest friends and fellow writers from Facebook groups the reasons why none of us has ever managed to win a writing challenge.

Why do I Fail at Writing Challenges?

First things first. There’s no failing or losing when you join a writing challenge. The ultimate takeaway comes from realizing how even if you don’t score that big chunk of gold on the other side of the rainbow. We are all collecting little white pebbles along the way that will help us further down the road to find our way and guide us across the writer’s labyrinth.

Does my writing suck?

At some point, all of us joining the conversation over on my Facebook group had that feeling.

Even you, dear reader, have already experienced that low self-esteem wave that engulfs you after spending long hours, days, or even weeks drafting a stellar piece to perfection. Only to watch with weary eyes your dreams crumble because your name isn’t among the winners.

Cleanse your mind from those thoughts, our stories are our children, and every child on earth is the most perfect, beautiful, little wonder to a parent. It would help if you always cherished your stories no matter what, instead of falling into depression because of them. Please remember how beauty is always in the eye of the beholder.

“One man’s toxic sludge is another man’s potpourri. “ — Grinch

Am I utterly unlucky?

Some look at challenges and swear that it’s all a matter of luck and that, ultimately, they are just the utterly unluckiest person on earth, and they will never make it because of bad karma or because the fault is in our stars.

There’s a certain degree of luck in any challenge; I’ll give you that. It helps when you get the right set of eyes looking at the competition. Maybe you’ll get lucky, and something in your piece resonates at that moment in time with that person in the jury.

However, luck doesn’t repeat itself. A bolt of lightning never strikes the same place twice. Thus, it’s not because of luck you aren’t winning any challenges.

“You know, Hobbes, some days even my lucky rocket ship underpants don’t help.”― Bill Watterson

How to Stay Motivated

Keep challenging yourself. The ultimate prize is not the leprechaun pot of gold at the end of the rainbow. You’ll come to realize there’s more value in those little white pebbles you find along the black tourmaline road.

When you listen to your muse and decide to follow the writer’s way, there’s no turning back. Take a deep breath, close your eyes, listen to your heart because, from then on, you will also be chasing rainbows on the back of unicorns for most of your life.

3 Key Takeaways

American poet Mary Oliver gave us instructions for living a fulfilling life.

Pay attention:
Listen to your inner voice and energize yourself. Look at your surroundings and breathe in all the wonders of the world.
Be astonished:
Let the wonder inspire you, and you are halfway there to greatness.
Tell about it:
Don’t let failure get to you. Please follow the white pebbles I’ve just laid out for you. Write your heart out and tell the world about it.

Follow-up

What's your take on writing challenges and prompts? I would love to learn from your experience too.

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How To Stay Motivated When You Lose A Creative Writing Challenge