5 Art & Design Challenges to Get Creative This Fall

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Written by Kellie Pcolar,
• 9 min read
Art Challenge Content Ex

I believe the first Instagram “art challenge” I had ever really heard of was Inktober. I remember thinking how awesome of an idea it was: Providing artists a way to motivate and direct their content to ultimately grow, both personally and publically.

Instagram really changed the game for us artists.

Back when I first joined Instagram in 2013, the app was sort of a free-for-all. Nobody was really sure what content to post, and nobody was really thinking too hard about it. For the most part, it was a glorified public photo diary of your day-to-day experiences. It was common to see Angie posting herself playing guitar, Jake posting a pic of his dog in the bath, and Beth sharing the egregious length of the grocery store line. Very similar to the type of content you see now, but with one large difference: it was being posted without the knowledge that it was content.

In fact, I’m not even sure the word "content" existed back then in the way that it does now — as a commodity, as a career, as a highly desired good and service.

Sure, content marketing has been around since Jello started sharing dessert recipes in Ladies Home Journal in 1918, but the notion of “content” didn’t exist until 78 years later (and even then, it wasn’t “content” as we know it so colloquially in 2021).

Okay, how does this relate to art challenges? Because Content made it possible for artists to “make it”.

It was the first time we could take a step back, look around, and realize the only barriers were ourselves. Sure, there’s plenty of other people who make bank from sharing all kinds of Content: tutorials, music, crafting, gaming, talking, eating, petting, running, and gated Content (the holiest of Content), to name a few. So, one could say there is finally a field for artists to play in, but really it’s anyone’s game. Regardless, we (as a collective of folks throughout the history of time whose soul’s desire was creation) are being seen.

Because “making it” in 2021 revolves around your Content, let’s talk through one of the best strategies I’ve seen artists use to SLAY the Content game: Art Challenges.

Everyone’s heard of Inktober—the famously popular Instagram art challenge that artists from around the world look forward to as soon as spooky season hits. Created by Jay Parker in 2009 as a way to improve his skills with ink, it soon grew into one of the largest art challenges on the interweb (and produced a LOT of Content — 21.8M on Instagram alone, to this day). Inktober inspired many other artists to start their own challenges within their own communities, and soon enough, challenges became one of the most popular ways for artists to put themselves out there.


The formula for “making it” in the art world today is essentially releasing enough quality Content to gain enough of a following to successfully make a living out of creating.

Sure, you could argue that your art is not mere content but an external representation of your emotions that you hold to the highest pedestal of expression, but once you subject your art to the black hole that is social media, it becomes Content, whether you like it or not.

Art Challenge Content Ex Example of engagement from a #creativeglowchallenge submission.

Why Art Challenge Content is good Content (not just for your audience, but for your personal practice, too):

It allows you to practice your craft on a regular basis.

Even if you don’t believe in “Content” or side with Michael Rock on the idea — Art Challenges at the very least help you create a healthy and consistent practice, even if just for a sprint. When else do you feel so motivated to create regularly — and share the journey? An art challenge brings the combined pressures of time and community to light a fire under your pen, brush, hands or mouse.
It eliminates the noodling on “what” and allows you to focus on the “how”. (Get unstuck.)

To help yourself and your practice, you’ve got to create regularly. That’s the only way to improve. Regular wins, regular fails — the more public, the better. Creating consistently not only helps your art, but it helps fill the internet with content directly attached to you so that you have more discoverability and ultimately, more fans. If you want to reach your goals as a creator, you’ve got to create often. And nothing is worse than staring at a blank canvas, like Harry in the beginning of AHS Season 10 (for anyone else watching).

A creative challenge has rules — barriers, guidelines, structure, guardrails — it tells you the “what” so you don’t have to spend any time figuring it out.

All you have to do is decide “how” you’d like to interpret it. And that’s the fun part that usually happens naturally in the making process. Therefore, there is no getting “stuck” — the regulations that come with an art challenge along with the deadlines makes it difficult to waste any time thinking too much. That’s probably my favorite part about all of this: less thinking, more making.

You become a part of a larger creative community.

As I mentioned in my article on the Hue Year’s Resolution Art Challenge I hosted back in January, the community that surfaces during creative challenges absolutely rocks. Everyone supports each other in so many different ways, whether that’s sharing each other’s work, commenting with uplifting notes, DM’ing you through your stories or shouting you out as inspiration. This community is not only awesome to inspire and motivate you along your journey, but it can gain you some loyal followers! Most of the time, participants follow each other and engage with each other’s work, which is a big boost in engagement for your account. And in many challenges, if you’re lucky, the host will share some of their favorite entries, which boosts followers and engagement for that account.

You can create a larger project out of it if you have time to prepare.

Basically what I mean is—the challenge can be as big or as little as you make it. Make the challenge your own! Don’t love the pressure of a daily challenge? Create one prompt a week, or don’t pressure yourself to post to your feed—stories function just fine for sharing work you don’t feel is “feed-worthy” (although I have a whole other article I could write about that notion). But if you’re really into the idea of going all out, you could go above and beyond and not only participate in the daily challenges, but coordinate beforehand to set yourself up to have 1 cohesive larger project in the end! For example, in the Hue Year’s challenge, the prompt was to create something that featured 1 particular color each week. I took this as an opportunity to make a larger piece from this prompt, challenging myself to create a collection of zines around the topic of past relationships in my life.

5 Creative Challenges you should absolutely take part in this fall:

Mab’s Drawlloween (Starts Oct.1)

Mab's Drawloween Example Art

Mab Graves has been hosting her Drawlloween Club for 7 years now, and with over 400k followers, she’s got a hell of a community. And for good reason — she’s highly talented, down-to-earth, and a proud member of the #sickgirlsclub. She leaves the prompts pretty open, which leaves a lot of room for creativity.

Creative Glow Design Challenge (Ongoing)

Creative Glow Example Entries

More of a designer than an illustrator? No problem! Abi Design, Queen of Content, runs a highly successful design account and releases semi-regular design briefs focused on a single color palette in which you need to design a brand! (Even if you don’t feel like taking the challenge, definitely check out her page as an example of how to keep your audience highly engaged.)

Brief Club (Ongoing)

Brief Club Example Submissions

Another one for my fellow designers — Brief Club is a highly aesthetic, quickly-growing community of designers who respond to weekly branding briefs. The results are pretty impressive. If you need some inspiration for some new spec portfolio pieces (or just need to keep on your Content grind), this will most definitely spark your fire.

Absurdist Collage Challenge (Ongoing)

Collage Club Example Art

Can’t really draw, can’t really design? Literally cut & paste images together as a form of expression, meditation, or just plain content generation with this weekly collage challenge. As you’ll find out, submissions truly span the breadth of this medium and leave plenty of room for play.

Visual Mixtape (Starts Oct. 4)

Visual Mixtape Submission Examples

This one is for all types of makers — videographers, photographers, designers, illustrators, painters, animators, crafters, builders, coders, and assemblers. The concept is simple: Create a piece of Art or Content that is directly influenced by a piece of music. You might choose to spend this challenge creating a series of animations for various songs by a single artist, or crafting collages based off of your favorite Spotify playlist. It’s starting October 4th, so get ready!


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