How I've Earned Over $4,000 from Vocal Challenges

by Kathryn Milewski 2 years ago in tips and guides / Challenges · updated about a year ago
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Tips and tricks I've learned from a year of making income through Vocal Challenges.

After my internship ended early from the coronavirus pandemic and freelance film industry jobs were left in shambles, I found myself with an overabundance of time and a lack of money. Fortunately, I remembered a little website called Vocal where I won a writing Challenge the year before.

It was a Game of Thrones-themed contest called "Eight Years Later." The prompt was to write about how the show changed your life for the better. I wrote a memoir comparing my life to Arya Stark's, and my story unexpectedly placed first. I received a $500 cash prize, which I used wisely this past summer.

When I logged back on to Vocal almost a year later, I discovered weekly Challenges had been added for creators. I cracked my knuckles, drank gallons of coffee, and got to work writing stories that would hopefully gain recognition from the judges. It took me nearly three months until one of my stories, an entry for the "Quarantine Playlist" Challenge, placed first.

But why stop there? I kept competing in Challenges until I placed in another one. And another one. And another one. This year alone, I've placed in five Vocal Challenges, and my total winnings since my very first contest win last year currently amount to over $4,000.

I've learned a few key lessons when it comes to gaining the attention of Challenge judges. Here are six tried-and-true tips I've used to exchange my stories for cash prizes.

Enter As Many Challenges As You Can

The fun thing about Vocal Challenges is that no matter how much you think you understand them, they are unpredictable. There have been a few times where I was sure a competitor's story would take home a 1st, 2nd, or 3rd place spot, only for three totally different stories to win. You never know what particularly moves the judges, or what makes them laugh or cry -- so don’t underestimate your work!

It's in your interest to enter as many Challenges as you can to increase your chances of placing in one. You'll learn so much from the experience and might even make some money from reads or tips.

One thing that's helped me get my work in more Challenges is subscribing to Vocal+. Doing so gives you access to special weekly Challenges. These are particularly beneficial because of their short duration. Because they only last for seven days and are only open to Vocal+ members, there's usually less competition. Definitely consider subscribing to Vocal+ if you want to take winning Vocal Challenges more seriously!

Think Outside The Box

The hardest part of competing in a Vocal Challenge, and the part of the process which should take up most of your time, is the brainstorming. You’re looking for an idea that isn’t just good, but unique.

My rule of thumb is that the second idea is often more profitable than the first. I say this because by the time it takes you to write, design, and publish a piece, chances are your idea will already be taken. A judging criteria for Vocal Challenges is originality, so half the battle is creating something no one else has thought of.

At first, I was discouraged to enter June's "Pets Welcome" Challenge because I did not own any pets at the time. However, I noticed most entries were about creators' cats and dogs. There were not many stories about animals besides those two creatures.

My family and I had taken a liking to a groundhog living in our backyard, who we named Ciabatta. I wrote a story about my experiences with her, and how she had given birth to baby groundhogs in our backyard. I was even able to connect my not-so-close contact with her to social distancing from the pandemic.

When I published my story and entered it into the "Pets Welcome" Challenge, it became an unexpected hit. It was a staff pick, placed first in the Challenge, and is still one of my most-read Vocal articles.

So while other people are creating stories about cats and dogs, write about groundhogs! In other words, travel off the beaten path with your Challenge entries. Doing so may increase your chances of winning, and ultimately provide more opportunity to make money - both off of views and tips. Also, make sure to read some of the other Challenge entries before submitting yours. That way, you can see if your idea is taken or not. Plus, doing so helps your fellow competitors secure reads!

Make It Personal

What would you rather read: a short article with a simple answer to the Challenge prompt, or a longer piece that answers the question, but also tells a story about how the creator overcame adversity? If you're like me, you would rather read the latter story. And so would the judges.

If you have the option to tell a personal story for a Vocal Challenge, always go for it. When I say "story," I mean something with a clear beginning, middle, and end. The higher the stakes in the story, the better. Even if it's something really emotional or embarrassing, your personal story is probably worth telling. The more vulnerable, the more compelling it is to an audience.

For September's "OG Celebrity Crush" Challenge, creators were prompted to write about their first celebrity crush: how they discovered them, what they're up to today, if the crush still stands, and of course, to include a picture with the entry. I had two options to write about:

1. Orlando Bloom

I knew my first OG crush was Orlando Bloom as Will Turner from Pirates of the Caribbean, but I didn't have a good story to go along with my answer. I first saw Pirates of the Caribbean in my aunt's car while on a road trip. I thought Will Turner was cute. Roll credits.

2. Jared Gilman

Instead, I did something a bit risky and wrote a memoir about my time working with Jared Gilman: the star of Wes Anderson's Moonrise Kingdom. While his character from the movie, Sam Shakusky, was not my first on-screen crush, I did greatly admire the character when I was in middle school. And yeah...I was a little starstruck when I met Jared in person.

After publishing it, my Challenge entry took the first place spot in the Challenge! (Yes, sometimes your cringiest memories really are worth sharing).

People are afraid to submit personal stories because they fear their experiences are too specific or inconsequential for others to enjoy. But if there's anything I've learned from studying memoirs in college, it's that the personal is the universal. Your unique experiences matter!

Follow The Prompt

While it's important to think outside the box and make your Challenge entries personal, always remember to follow the writing prompt Vocal provides. I've made the mistake of spending weeks on a Challenge entry, only to learn after submitting it I took too many creative liberties and made something outside of what the judges were looking for.

Because I don't want you wasting time making the same mistake, I urge you to carefully read the summaries the Vocal team leaves on each of their Challenge pages. Do it before brainstorming, then do it again once you've finished your story to make sure you got everything you needed.

In the Challenge summary, the Vocal team will usually leave questions they expect to be answered in your story. Answering them correctly, clearly and thoroughly is your key to winning. Think of writing a Challenge article like writing an essay for school: the better you answer the questions, the better your grade will be.

Additionally, don't forget to include pictures, videos, or links/other media if the prompt asks you to! Unfortunately, I've seen so many Challenge entries where the story was superb, but the entry didn't win because the creator forgot to include the required media. Winning a Vocal Challenge requires a balance of being creative while also staying within the guidelines!

Use of Rich Media

Segueing into media - using a variety of pictures, videos, and links can help your Challenge entry stand out amongst others. While Challenge judges don't judge a story by its cover photo, presentation does matter.

If you're talking about someone in your story, include a picture of them if possible! If you mention a company or your favorite influencer, embed a link to their Instagram page! Audiences are drawn to work that is eye-catching and interactive. The goal is to make your entry look like a magazine article rather than a black-and-white page from a novel.

If you need help finding good pictures to fill up blank space, try using the Unsplash feature.

You can search for high-quality pictures that will surely make your article pop. Plus, you don't have to worry about copyright!

Also, don't forget to take advantage of headers, bullet points, and block quotes. Anything you can do to make your Challenge entry look more professional is worth the time and effort.

Promote Your Work On Social Media

After you've published your Challenge entry, don't forget to share it on social media so your friends, family and community can enjoy it! If a tie occurs when the judges are grading Challenge entries, they will take reads and likes into account when determining a winner. Therefore, it is important to promote your work as much as you can, just in case your entry happens to be in a tie.

A good platform to use in particular is Instagram. Vocal’s Instagram account shares Challenge winners on their daily stories. If you happen to win a Challenge and have an Instagram account the Vocal team knows of, they will tag you when they post the results!

Facebook and Reddit are also good platforms to share your stories. This is because Facebook has groups and Reddit has communities that cater to specific interests. For example, say you write a Challenge article about a new beauty product you love. If you share your story with a beauty-related Facebook group or Reddit community, the higher the likelihood strangers will read your story and drop it a like.

You don't have to share your stories on social media in order to win a Vocal Challenge, but it always helps. After all, we write on Vocal so our work can be seen by an audience. If your entry doesn't place in the Challenge, promoting it on social can help you secure money from reads, and maybe even a few tips!

And speaking of tips...that's all the tips I have for you today, dear readers. If you would like to learn more about doing well in Vocal Challenges, I have an extended article with more advice you can check out here:

Also, the Vocal team has a resource article that explains the judging criteria for each new Challenge posted on the website. Make sure to check it out if you would like a better understanding of what the Challenge judges are looking for.

Hope these tips and tricks help you in your next Vocal Challenge endeavor. Wishing you the best of luck, and happy writing! :)

For a complete list of resources for Vocal creators, visit our Resources page here.

tips and guidesChallenges

About the author

Kathryn Milewski

Insta: @katyisaladybug

Also a blogger at

Playlists, memoirs, and other wacky pieces.

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Comments (5)

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  • Rose Rossenbach2 months ago

    Thank you so much, this was very helpful! Reassuring what I thought I needed to too! Just entered in my 1st challenge and submitted in 2 stories, we shall see how I do!

  • EJ Baumgardner2 months ago

    Wonderfully insightful and everything I hoped to find within. Superbly written.

  • Linda Rivenbark2 months ago

    This article is just what I needed to read. Thank you for all the tips.

  • Luisa Gillies2 months ago

    Very helpful, thank you!

  • Nitia Johnson3 months ago

    This was very insightful. Thank you.

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