The best Art Challenges to push your illustrations further!

There was a debate on my Facebook feed not too long ago where a fine artist expressed some disdain for gimmicky challenges and the seemingly endless list of pun-intended named months of the year dedicated to some sort of bandwagon art challenge.
It does seem as though there isn’t a single time of the year not labelled and themed, but before we think too much about whether this is an expression of attempts to gain capital by the creators or a show of herd-mentality, I think it’s better to focus on the question more relevant to artists navigating their development.


Are Art challenges worth your time?


As with everything, of course, it depends on where you are in your development and what it is you hope to gain. If you desperately need pieces for your animation portfolio, then perhaps spending 31 days on inktober isn’t for you. But there are times when certain challenges can be very helpful indeed!


1. You need to practise one particular discipline, and the challenge lends itself towards that.

2. You’re lacking direction and are deep in an art-slump! If you’re low on ideas and don’t trust yourself to come up with something good to draw, there is nothing wrong with borrowing some direction.

3. You want to give your social media a boost by posting consistently and getting your followers invested in a project.

4. You’re never drawing the same subject matter or style and your portfolio could really use a demonstration of cohesively themed work.

5. You want to challenge yourself! Finishing an art challenge is difficult, and if you make it, you have every reason to be proud of yourself. Now you know you can consistently work towards a goal and finish a thing! And in the end, finishing things is the most important! No need to express it any more eloquently than that.

Here’s just a small list of the best art challenges I have come across.


1. Inktober


Inktober is only the most famous art challenge EVER! Created by Jake Parker, comic, animation and children’s book illustrator in 2009, this challenge has you creating one ink drawing a day for every day of October. That makes 31 drawings in which to improve your inking. Each year, there is an official prompt list you can follow, or you can do your own thing.


There are a number of variations people have added over the years, like witchtober or faux-inktober. Really the goal is to create something new every single day, and post it to social media to hold yourself accountable via your friends and followers.
If you haven’t worked in Inks before, this is a great chance to practise your line work and hatching.
I’ve participated in Inktober 2019 and finally managed to complete the whole month! It was indeed challenging and I got a lot out of it. You can read about my experience here!


2. Character Design Challenge


The CDC is a group on facebook that posts a new character design theme every month and lets you post your design to their group. You can win features and cool art books, and gain plenty of feedback from the large and active community surrounding the challenge. The team also posts their favourites to their instagram account, so it’s a great way to challenge yourself to create one awesome design each month, get feedback for it, and gain some exposure.

The group has over 204k members and many active contributors so you’re also sure to find plenty of inspiration and new artists you will like.

3. Hayden Aube’s character quest

Hayden Aube has generously created 30 free character design prompts that you can subscribe to in order to receive one new cool prompt per email every day.The prompts include a story snippet and a special challenge if you’d like to take the difficulty level one step further! They are really creative, out of the box ideas to make you come up with characters that you wouldn’t have thought of on your own perhaps, so if you’re lacking ideas and just need to learn how to work to a brief and interpret a rough prompt, this one is amazing to help you push your character design abilities.


4. Will Terry’s “Draw 50 Things”

Children’s Book Illustrator Will Terry has birthed this amazing little challenge. The concept is quite easy – challenge yourself to draw 50 objects in one picture. “Objects” can be anything, whether they are creatures, objects or people. The goal is to create a scene that is brimming with detail and life to showcase your ability to compose and complete an image with that level of complexity. When was the last time you included even twenty objects in your images? The benefit of completing this one is clear: You gain a portfolio piece that will let your clients know that you can handle detail and have the imagination to fill a whole room!
Check out Will Terry’s video on drawing fifty things to learn more.

5. Draw-this-again

I should redraw this again in 2020! This was my progress in 7 years, and whilst the 2016 version doesn’t impress me now either, it’s a massive step forward from my teenage-skills!

No doubt this challenge won’t be new to anyone, and I am not even sure once can consider it such. It’s common practise for this kind of image to go around various art youtubers and instagram artists. Draw-this-again is a simple prompt encouraging you to take an imagine you once drew and were proud of and draw it again years later, incorporating all the progress you have made.

Whilst I’m not sure this challenge really pushes your skills and makes you learn something new, I have found this to be a great way to get out of art slumps and breathe self-confidence back into me. Sometimes it takes looking to the past to really understand how much you’ve grown as an artist, and this will really make you notice the difference. Your approach, your skills, your style, all will have changed in the years since your last piece, and what you once struggled with has become so much easier.

Reminding yourself of your progress is a real boost. And just because old ideas might have been poorly executed doesn’t mean that they weren’t good concepts – I often find myself looking back on an idea I didn’t have the skill to draw but could finally find the right way to express. It’s nice, realising a vision my past self could only dream to put on paper. So if you’re feeling down about your art and need to just draw something, do this!

6. Draw 100 Somethings

This is a tough one, no doubt, and likely to feel tedious and difficult. But it is oh so worth it. The challenge is simple – pick a subject matter and draw a representation of it 100 times. You can take all the time you want, but one a day is a good rule. Common subjects are things people struggle with a lot – hands, feet, heads. An art buddy of mine sat down everyday and meticulously drew an elephant.

The takeaway from this is all about muscle memory and practise – after having drawn something 100 times you should see a real improvement from the start, so long as you’ve paid attention and adjusted your process. The drawings don’t have to be anything special. Pencil sketches will do! This establishes a great study and practise mentality that can lead to breakthroughs with all kinds of areas you might be struggling with in art. Once you do something often and regularly enough, it can become a habit. Getting into positive habits, like drawing at least half an hour every day, can make all the difference for your improvement.

7. Draw this in your Style

This is an Instagram favourite, and a nice way to connect with other artists and approach an illustration playfully. Other artists will put forward a character of theirs in their style and prompt you to draw the character in yours. This can just be an illustration done in a couple hours of your spare time. It’s unlikely to further your career or push your skills, but it can be a good prompt when you don’t know what to do and push interaction with the community.

Plus, it might help you think about what your style actually entails – if you had to take an image and turn it into something anyone would recognise as yours, how would you go about it? What makes up your style? Is it line weight, texture, colour choices, shapes? Really looking at the prompt image and figuring out what you would change to make it yours can really help you understand that better.

8. Slowvember

This is another great challenge promoted by SVS children’s book artist Lee White. Slowvember takes place in the month of November, and is a change of pace from the very busy and fast paced Inktober challenge. This challenge has you draw one image during a whole month – but here’s the key: You have to try and make it the best thing you can create right now.

That means going through the full development process. Lee White suggests to take the first two weeks to sketch and conceptualise, then use the remainder of the month to render.

Steps include researching your topic, doing 50 or more thumbnails, working up some more detailed favourite sketches, creating colour comps, and finally detailing and rendering your chosen project. I won’t go into too much detail as Lee himself talks about the challenge in his ‘How to Slowvember’ Youtube video. I am also not yet master of my own process, so go and learn from a pro on this one!

At the end of the month you should have a portfolio piece that demonstrates the best of your ability and you will have practised professional habits and development strategies. If you’re working on a portfolio and want to go through all the motions you would for a professional project, Slowvember really helps getting you that practise.

Are you planning to join an Art Challenge this year?

I hope you enjoyed my list of art challenges I think can push your illustrations further and give your portfolio more substance this year. Mostly, though, these are all fun ways to engage with your arts community and try something new!

Of course the list of art challenges is much longer than what I have presented, so I’d love to hear from you. Which art challenges have you tried in the past? What did you learn from them, and do you plan to take any challenges on this year?

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