How I finally finished an art challenge
The benefits of gentle, sustained effort.
Last week, I finished a 30-day art challenge for the first time. I completed 33 paintings/sketchbook pages in a single month! Before that, I always gave up on these types of challenges somewhere along the marathon and wanted to figure out why.
Why was it that even though art is my job, I couldn’t find a way to finish these challenges? What was it that made me stop? Why did I feel like the things I made were failures? What was fueling the motivation of others to keep going?
This last month, I found answers to these questions and was rewarded with a definitive and confident new direction for my art style. Let’s talk about it so you can also bend the rules and benefit too.
What is an art challenge?
You have probably heard of the concept of an art challenge, but if you haven’t here’s the deal: The goal is to make art daily within a certain theme or in response to a prompt. A lot of these challenges also call for artists to post their work daily to social media. That is a big added expectation.
So, big ask right? Not only should you make art everyday in a way that will challenge your work, but also, you must share each step of the way publicly.
The rules for the popular challenge, Inktober are as follows: Draw with ink daily for 30 days in the month of October, responding to a set of prompts. Then post your work with the hashtag #inktober.
Here, a problem arises. When we approach challenges as a performance while we are trying to grow our work, it’s not going to feel good. Growing or pushing a new skill is a process through which we will fail, make lots of mistakes, and let weird stuff happen. This is often why people take classes or get art tutoring to get guidance around while also having to perform and share to platform protocols, it is a recipe for disaster.
Art challenges need to be things we do in a retreat or hermit state of creative play. These are things that we should do alone or with a small trusted community, not as a performance the larger social media apparatus. Posting daily benefits the bottom line of these platforms, not our individual growth.
The framework of challenges is useful to push a particular set of skills or parameters we want to improve in, but the compulsion to post while in process, should be abandoned.
Failure is imperative for growth.
I have been teaching art in classrooms since early 2012. Seeing my students struggle with new concepts and challenging techniques but often stumbling gorgeously. In each of their attempts, I try to guide them through gentle feedback, highlighting their discoveries, guiding their voice to keep trying. Often I hear students being so self deprecating when they are making brilliant progress. Our culture teaches us to be “A” students, to focus on product and not process.
Giving an art challenge where I forced students to post their vulnerable growth on social media would be uncompassionate and cruel.
Say you are trying Inktober for the first time. You have a set of challenging and varied promps, and a new medium to work with. This is a brilliant self directed study if you are trying to learn value, improve line work, or get more comfortable responding to narrative prompts. This can be really helpful if you want to get into making better comics or client work. At the root, this challenge is a brilliant way to grow as an artist.
But let’s imagine you are going into this a little new. Ink isn’t your primary medium, and it’s permanant. If you think watercolor is tricky, give black ink a whirl. Suddenly you are working with a material you can’t erase or lift. You might be trying out new tools, surfaces, or markmaking. This process is going to pose really interesting challenges, no doubt. On the surface, for an artist this is good! Growth will happen when we do hard things over a sustained period.
Challenging our creative hand and ingrained habits is going to help us become better artists. We also need compassionate community to help support us.
If you are in the East Bay, I have three new classes at Community Arts Walnut Creek that just opened for enrollment. I’m teaching an introductory drawing course, a beginner watercolor painting course and an open studio for all intermediate students to come make in community with me. Classes start the week of May 20th and are filling up fast so snag your spot!
Social Media is a cruel critique room.
When I was in art school, I dreaded critique days. While I had a few members of my cohort who made incredible work and gave helpful feedback, the rest of my classmates felt like wolves.
We were expected to perform our vulnerable growth for a range of fellow students with competing motives. Folks would often tear down the very concept of making representational art. Conversations would wander into deeply unhelpful, ego-fueled inquiries that made me question my very existence as an artist. I almost dropped out, twice, due to straight-up harassment from students in critique rooms that certain faculty allowed and encouraged.
This is why the social media posting expectation in these challenges bothers me. If you have a private account with just your friends, maybe it can feel good. But more than likely, posting each phase of yourwork is counter-intuitive and discouraging. Just like art school critique, you are offering up your evolving creative voice to a new set of wolves — tech-bro-tuned algorithms.
Comparison traps are too easy on social media. Seeing your developing drawing under a hashtag alongside a much more skilled artist will likely kill your creativity or your drive to practice. Imposter syndrome abound.
Comparing yourself to other artists in a hashtag is supposed to be an exercise in inspiration. That is never how it feels for me. It always feels like a setback. A warning that while I might be good, that other artist is incredible.
Then, you add the layer of measurable metrics. How engaging was your caption hook?! What were numbers of likes, views, imprassions, and comments — the new cultural symbols of “success” These metrics compete directly with the creative growth you are vulnerably putting on display for each post. These metrics distract us from the true point of why we want to make in the container of a challenge.
I knew this heading into Plein April, so I did the challenge without the pressure of sharing while doing it. Quitting Instagram in January helped. I shared an occasional shot from my easel, but the further along I got, the more I wanted to quietly sit and reflect on the Quality of each drawing or painting. Instead of thinking about post metrics or comparisons, I would ask myself “what did I get right, and what did I get wrong here?”
I think that art challenges require a quiet reverance, a mindset of retreat, an occasional check in with a trusted community on something like Discord where there isn’t an an algorithm or metrics to measure can help you keep going.
So here are my final tips for you if there is a challenge you are wanting to try,
Find a challenge that is directly related to a skill you want to build. I chose Plein Airpril because I wanted to get better at working from life in oils and gouache. Think about the challenge from a perspective of self improvement, rather than what is trendy.
Know yourself. What kind of support keeps you motivated? Can you text a friend who is doing this with you? Do you need to setup a tutoring session with an artist you admire to get gentle feedback and guidance with each step? Set your own list of rules and rewards that will keep you motivated outside of social media posts
If you choose to post, don’t you dare look at metrics. This is what made me stop Peachtober back in 2023. Feeling kind of bad about an artwork and then seeing a post not performing well? Yeah, stop that. These platforms essentially have “credit scores” on us about our work performing at a certain quality or caliber. This could really harm your reach and ability to get clients to “just post everything”
Never a failure, always a lesson. With the work that fails or flops, what did you learn? Did you realize the type of paper you were using doesnt work for the technique, or that you liked the shapes but didnt like how the paint performed? Use these paintings as roadmaps and opportunities to help you grow.
Finally, remember that you create the boundaries and rules for a challenge. Do you only have 2-3 days a week you can paint? Great, spread a “30 day” challenge over 10 weeks instead. This might even have other advantages as you can spend more time journaling and thinking about what you make after each session.
Let me know in the comments below if this helped you feel inspired to try a new art challenge.
If you want to see how this impacted my work, I made a video about my growth in retrospect. Posting on a social platform after completing the challenge. It’s over on YouTube and you can also watch it here:
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