18 Art Challenges to Up Your Skills and Engage Your Audience

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Art challenges are used in a variety of ways. The vast majority of them are designed to test and improve your skills.

These were primarily the ones I wanted to focus on but as I explored what is out there it made me realize that art challenges are useful for so much more than making you better at art.

Some are made to showcase your work and stimulate social engagement with whatever audience you currently have. Others are meant to help you network within the art community.

They can be useful for building up your portfolio and spreading awareness of your work.

Especially if you can get on one when while it is the current trend. In the meantime here is a collection of challenges you can give a go.

Paint With Coffee Challenge

For the Paint With Coffee Challenge, again, very aptly named.

I feel like to be even remotely good at this one you need some experience with watercolor paints.

On the flip side, perhaps if you don’t have experience with water paints doing this challenge will inspire you to try those next.

In the video above Jazza takes this challenge on. Jazza actually has a whole playlist of 268 videos where he is conducting different art challenges!

He is pretty much the master at this. The challenges he does though are a bit grander and most are for entertainment.

While I’m sure they indeed are challenging and have made him incredibly versatile as an artist, for regular folks like us let’s just stick with what is reachable.

That said, being the master of art challenges Jazza has created a great app that will help us with our next challenge.

Randomly Generated Drawing

This one is a fun one to do. By yourself or with friends!

It challenges you to figure out how to illustrate strange combinations of details and characteristics that make up a particular character. It doesn’t have to be just a character but that is the most common one you will find people doing.

There are a lot of videos on YouTube of people doing this too. Of course as I was researching art challenges one of my favorite YouTubers Ten Hundred released a new video covering just this thing.

In his video he uses a website for quick character generation found here. I actually recommend watching it not just to see how it’s done but it was pretty funny.

That said, that particular character generation is too much in my opinion. For the purpose of drawing it provides too many unnecessary details which look like they are more meant for role playing games.

It can be distracting from what the challenge is intended for.

I actually tried this with a friend last night using Jazza’s Arty Games app you can find in the app store of your smart phone.

In the app, you have the option of doing a variety of randomly generated challenges.

There is the color challenge, character challenge, environment challenge, incremental challenge, scribble challenge, copy challenge, design mix challenge, and custom generator challenge.

These are all different ways to challenge your art skills in a random and really fun way. There is a timer you can set anywhere from 1 minute to 60 minutes too!

I highly recommend trying it!

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The One Marker Challenge

The one marker challenge is an art challenge where you randomly choose one color from your set of markers to make a picture with.

This one is mostly meant for illustrators who have a collection of Copic markers on hand. It perhaps could be done digitally as well and maybe in some other mediums where you can potentially get multiple tones out of one color without needing to use any others.

The challenge in this is figuring out how to get different tones of color with just one marker. In the video above, the artist and YouTuber Hullo Alice really captures what I feel is the proper mindset to have for this challenge.

What is the most effective way to use this marker?

Hullo Alice

You should be asking yourself how you can get the most out of this one marker.

There are only so many different tones of color you can get with one marker.

How you approach it is entirely up to you as long as for your coloring you only use the one marker.

People seem to be on edge about what you can and can’t do in challenges and I think the most important thing is to recognize the function of the challenge.

For this challenge, some people start by sketching out their ideas, then drawing it with a pencil, then inking over it to get a more finalized illustration that is ready for color. Other’s I’ve seen use extra things like rubbing alcohol or water to help get different variations in their colors.

I think all of these approaches are totally fine to do.

The core question of this challenge is what is the most effective way to use this marker? If this were the only marker you had or the only marker you could afford, how can you get the most out of it?

The featured video by Hullo Alice is a really great example of to do this challenge right in order to push your coloring skills to the next level.

Hashtags: #onemarkerchallenge

100 Heads Challenge

The 100 heads challenge is an excellent challenge to help any artist out there that struggles with heads.

For the challenge, you are to draw 10 heads a day over the course of 10 days.

You want to draw them from every angle you can think of. Push your abilities to their limits and do your best to stretch beyond them.

You want to try to draw portraits of people of all ages and races. Try to practice your composition and anatomy of the head. Do a few skulls if you need to for extra anatomy study.

The original creator, Ahmed Aldoori, started the challenge in January of 2019 and it is still a popular challenge today!

Which makes sense as it’s not too steep of a challenge and something that if completed is sure to improve your skills.

We could potentially extend this approach to other parts of the body as well. Doing ten of anything every day for ten days in a row like that is bound to help level up your skill on whatever it is you decide to put that kind of focus on.

Hashtags: #100headschallenge, #100headchallenge, #100headsin10days

The Art Style Bend Challenge

This challenge is meant to not only take you out of your normal style or elements but also get engagement from your audience.

You actually need some sort of following or audience on some platform to do this challenge. Whether that is on Instagram, TikTok, YouTube, or Twitter the idea is to go to your audience and ask them what is unique about your style or what should be swapped in it.

Whatever they respond with you take and instead of doing that thing you normally do you either bend it into something different, replace it with some other detail, or take it out entirely.

This helps get your audience to engage with you and pushes you out of your comfort zone forcing you to explore something you might not otherwise.

Alternate Hand Challenge

This challenge is more for fun and entertainment than skill or engagement.

It is commonly referred to as the left-handed challenge. Since not everyone is right-handed I decided to rename it the alternate hand challenge.

This is when you draw a picture with your dominant hand first and then try to draw it with your non dominant hand to see how well you can do.

This obviously will result in something hilariously awful and at the very least make you feel pretty good about your current skill level with your dominant hand!

In fact, if you ever feel like your art sucks just try this challenge!

The Art Blob Challenge

This is a pretty fun one to do. I’m not entirely sure what skills it exercises other than perhaps your drawing and visualization skills.

The idea is to put blobs of paint or color down on your surface in random shapes and sizes. The ones that I have seen done either use watercolor or do it digitally.

I did mine digitally.

Once you have your blobs of color laid out you then come back and draw into them what you see. It’s essentially a format of random prompting but instead of being computer-generated, it is prompting your subconscious mind to spit something out.

When I did mine I thought it had to all be faces and you had to use only the blob itself but after checking out how a lot of other people are doing it you can do whatever comes to mind really.

Many people will add additional things to the blob depending on what they see it as.

30 Day Original Character Challenge

The 30 day original character challenge is where you take one of your original characters and draw them in a series of different situations for 30 days in a row.

There are a ton of different 30 day prompts floating around out there. All you have to do is search original character challenges to find a whole bunch of them.

They include things like drawing your original character in an awkward situation, partying hard, or even stepping on a lego.

The purpose of the challenge is to have you push your style and character to places you may not have taken it without the challenge. Venturing into foreign territory is what a lot of challenges are about.

It forces you to encounter new problems you may not have encountered on your own.

365 Day Art Challenge

This one is clearly designed to help you develop a daily art habit.

This probably goes without saying but you’re supposed to produce one complete drawing, painting, or work of art every day for a full year.

Of course, there are people who do 100 days, 50 days, and 30 days too. It’s entirely up to you how long you want to go for but I would recommend choosing a number you know you can complete.

It is important to finish the challenge once you start it otherwise you won’t get as much out of it. One of the main points of doing challenges like these is to help forge the habit of making art into your everyday routine.

It is always fun to watch someone taking one of these challenges. I’m sure we all know how tough it can be to formulate a new habit so I can’t help but cheer anyone on who takes this challenge.

Making a painting every day for the whole year would definitely be hard for me to do. Maybe I’ll give this one a go next year.

The Inktober Challenge

Inktober is probably one of the most well-known art challenges out there. Heck, I can remember encountering people doing it well before I got into art.

Originally created in 2009 by an artist named Jake Parker this challenge has grown into a yearly worldwide challenge in the art community.

The challenge occurs every October and every year there is a new list of prompts. The graphic above is this years prompts coming up for the challenge next month.

The idea is to make the drawing in ink and post it on social media with the hashtag inktober and the respective year of the challenge. So this year it will be #Inktober2020.

It is perfectly fine to do a pencil under drawing and then ink over that too. Whatever it is you prefer to do.

Pretty much any 30 day art challenge has the intent of formulating a daily art habit.

While I personally don’t think you should do less than 30 days the creator of this challenge says if you want to do every other day or even once a week that is fine too. As long as you are consistent with it.

If you don’t do it in consistent intervals throughout the month then you essentially aren’t meeting the challenge.

The Art VS Artist Challenge

This is a challenge that originated sometime in 2016 and is still going strong today.

It is where you, as the artist, create a collage of 9 images. You put a selfie of yourself in the center and then pictures of your work around you.

This challenge isn’t so much about the creation of the collage or even the artwork as it is about self-presentation and audience engagement.

Many times as artists we focus too heavily on only posting the most carefully choreographed pictures of our works. We forget that it helps to show ourselves from time to time.

It’s hard for an audience to develop a personal connection with the artist if they don’t even know what you look like. That personal connection should be a key part of any good artist’s marketing strategy.

At least that is what some of the best in the business say. Sergio Gomez was discussing this in a recent Next Level Podcast. It was in podcast 246 “Marketing in the Now with Marine Costello”.

She says that if you show your face in a picture it will get twice the amount of engagement. So by participating in this challenge you can give your audience a little piece of you and hopefully make more of a personal connection with them.

Draw This Again Challenge

The draw this again challenge is a really cool challenge where artists attempt to make the same piece of artwork again over time to see how they have improved.

What you do is take an old piece of artwork and try to make it again. Something from a previous year in your art journey.

Only now you can apply the past years worth of development, practice, and insights into it. It’s a way of seeing how far you have come in the past year or years you have been doing art.

To me that is the best part about this challenge. It can be hard to see your own progress when you are submerged in your own work day in and day out.

It helps to take a step back and do something you have done before to see how your motor skills and visual library have improved over time.

Perhaps you will be surprised at the huge difference in results.

The Art Styles Challenge

This challenge, like a few others on this list, comes in quite a few variations.

The staple rules to the challenge are to take one of your original characters and then try to create that character in the styles of well-known animations.

I’ve seen posts that do a range of anywhere from 5 different types of styles all the way up to 25 or more.

It looks the most recently trending way to do it is to show two rows of characters in different styles. In the top row on the left is the original character and the rest of the characters are in the design style of things like Disney.

There are a lot of common ones people try doing. Here is a quick list I have collected to give you some ideas of styles to make your character in.

  • Attack on Titan
  • Gravity Falls
  • Adventure Time
  • Sailor Moon
  • Power Puff Girls
  • Tim Burton
  • Steven Universe
  • Futurama
  • Studio Ghibli
  • Attack on Titan
  • Goof Troop
  • Scott Pilgrim VS the World
  • Pokemon Dragon Ball Z
  • Gravity Falls
  • Adventure Time
  • Sailor Moon
  • Power Puff Girls
  • Tim Burton
  • Steven Universe
  • Futurama
  • Studio Ghibli
  • King of the Hill
  • One Punch Man
  • Rick and Morty
  • Fairly Odd Parents
  • Gorillaz

You don’t have to restrict yourself to just these either. If there is some favorite animation or art style out there you really want to try now is your chance!

Break out of that art shell!

Face Your Art Challenge

The face your art challenge is commonly mixed up with the Art VS Artist challenge. It looks similar but is a totally different challenge.

It’s similar in that it is another grid of 9 pictures. This time ALL of them should be of your artwork.

More specifically, they should be the cropped images of the faces in your artwork.

It is difficult to pinpoint what this challenge is truly about. I would say it looks like 90 percent of the people participating in it are just putting together a collage of faces.

After reaching out to a few people on Instagram to see what it was they got from the challenge it does seem some people actually will notice aspects about the faces they make that need to be corrected.

That seems to be rare though. It appears most people use it solely for the exposure.

Hashtags: #faceyourart, #faceyourartchallenge, #faceyourart2020

Character Design Challenge

The Character Design Challenge is held every month by CharacterDesignReferences.com.

While I have yet to figure out who is running the show they have a Facebook group you can join here to participate in on this month’s challenge.

A new challenge is released on the 7th of every month. There are different rules and guidelines to follow as well as professional artists as judges.

Beyond that, this particular challenge even has a series of prizes you can potentially win if you become one of their Patreon subscribers.

To check out the current challenge they have going on right now go to this page on their site here. They have a live timer counting down the time left until submissions end.

There will also be a list of all the details of the current challenge running.

Toon Me Art Challenge

The toon me art challenge was really popular when I first joined Instagram back in February of this year. I think it was around that time it started to die down in popularity.

It’s basically when you take a selfie and you turn half of it into a cartoon style drawing as you can see from my terrible attempt at it here.

If you search for the hashtags toonme or toonmechallenge on Instagram you will find many examples of how it is done better than this. That’s the point of these challenges though right?

To take us out of what we would normally choose to do and outside of our comfort zone.

Drawings Based off Usernames

This one is a fun one to try and it is a great way to engage with your audience and add a bit more of a personal touch to your interactions.

I just hit 200 followers this morning and in the spirit of writing this page decided I was going to give this challenge a try.

I posted a video here of me asking anyone who saw it to challenge me to draw their screen name. I’m honestly glad I only got a few responses as this is definitely pushing me beyond my comfort zone.

Drawing characters is something I have spent very little time doing. Now is the time to fix that though!

Basically though that is what you do. Tell whatever audience you might have about the challenge and ask them to comment that they want you to try theirs and then proceed to try it for those who responded.

Monstergirl Maker Challenge

This one I found on TikTok. Originally issued by the user Lis-ard, it took off and there are over 5 thousand videos of people showing off their attempt at this challenge.

This is one of the cooler things about challenges in video format. Especially when on something like TikTok that allows you to use someone else’s audio.

People end up grabbing the original audio of the person issuing the challenge and running with it.

Anyways, this challenge is about drawing a monster girl.

First, you make your monster girl’s skin color your favorite color. Then, you make her eyes the color of your birthstone.

After that, her hair should be the color of your shirt. If you wear glasses then add a third eye or a second set of eyes.

Next, add your favorite animal’s body part. So if your favorite animal is a dog maybe a snout or floppy ears.

After that add whatever else you want and then show it off with the hashtag monstergirl. You should probably do it in a video on TikTok or IG Reels since it was originally a video challenge.

Drawing Phobias Challenge


DRAWING people’s fears! Nyctophobia-darkness-I’m not taking more requests #art #artchallenge #viral

♬ original sound – r

This is another TikTok challenge and I was particularly impressed by this one.

I’m not normally a fan of creepy horror stuff but I guess it’s a combination of factors I find intriguing about this one.

First in the challenge is to find a clinical term for a particular type of fear or phobia. Like Achluophobia, the fear of darkness.

Once you have your term you then make a simple picture illustrating it. One of the ones I saw doing the fear of darkness showed a very simple light switched flipped off. I decided to go find it and embed it as the feature for this section.

Part of the trend is to set it to the original sound weouthomie found in the TikTok library.

Then, as you can see in the video, you do a transition where you drop the camera in all the way to the surface of the art and then pull out on the next clip showing the piece of artwork.

The next picture should be a far more well done drawing of something creepy illustrating the monsters crawling out of the darkness.

So it goes from simple and calm to complex and creepy. I recommend checking some videos of this one out. Better yet give it a try yourself!

Marc Spagnuolo

Hey there! Thanks for reading my article! I'm Marc the creator of this website. I'm a growing artist and web creator seeking to share what I'm learning in the hopes that it helps someone out there like you. I hope you found this information useful. If you're interested in learning more about me and my story click on my name or on my picture!

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