How to Design a Successful (and Feasible) Yearly Creative Challenge

Starting off a new year reminds me of buying a very expensive, luxurious sketchbook. It’s pristine, full of possibilities, and ready to be filled with beauty. You get excited, thinking of all those spreads you’ll create: no mistakes, no shaky lines, no ill-chosen color palettes. In your mind’s eye, it’s finished and perfect already. But when you open it, you get paralyzed by the fear. Every line and dot carries a possibility of failure, so you give up even before you started, or you throw in the towel at the very first lapse. That’s it, you’ve ruined everything again!


Such thinking prevents a lot of artists from starting or sticking to a long term creative project. Painting for 365 or 100 days straight appears to be impossible. Heck, sometimes even 30 days seems too much! And it can be if you try to churn out perfect, finished artworks day in day out. But it’s not what these kinds of challenges are for. And I learned this the hard way… Here are several truths about long term projects I discovered in the past five years, after completing four 100 day projects and doing one yearly challenge that sadly ended after 300 days…


Tips on designing a successful yearly creative challenge




Regular, self-imposed creative practice allows you to hone your skills, discover new techniques, and develop your style. But only if you give yourself a room for experiments and mistakes. If you’re not willing to make a mess and create something ugly, you’ll hinder your growth. Sure, you can stick to what you know and produce only perfect pieces (at the level you’re currently on), but this strategy will lead you nowhere in the long run.


Creating 365 finished paintings won’t necessarily make you a better artist if you’ll play it safe and only do things you’re already good at.  Long term projects are all about learning and growing and leaving your comfort zone. Give yourself a specific direction, decide on what you want to improve, and focus on one thing only for the season.


What if you learn about a particular technique and do some sketches on the first day. Then perhaps try to paint several elements and explore color palettes on the second day. And on the third day, you can assemble these bits and pieces into full illustration. Seems much more feasible, right? The key here is to take consistent action. The fact that something isn’t finished does not render it worthless. It’s the effort and progress that counts, even if all you have is 15 minutes a day.




You can do it as a hobby or because you plan to grow your portfolio or turn your art into a business. But if you want to tackle a long term challenge just to get more social media likes and follows, then you’re in for trouble. Not every project will take off, and you’ll burn out chasing the vanity metrics. What is worse, if the project won’t resonate with people, you’ll start doubting the whole purpose of your endeavor. Do yourself a favor and focus on having fun, growing your skills, and/or planning your career path. Instagram fame is only icing on the cake.




Ask yourself, what will you gain, when you’re done with your yearly challenge. If you want to become a surface pattern designer, your end goal might be creating a cohesive textile collection and uploading it to Spoonflower. If you dream about being a children’s book illustrator, you can illustrate a popular tale and expand your portfolio. A clear purpose will help you get through these tough days when you feel like quitting.




When deciding on a topic of your challenge, avoid being too vague. Likewise, don’t impose too many restrictions on yourself. If the topic isn’t broad enough, you’ll get bored out of your mind very quickly.


I’ve chosen “ocean” as an overarching theme of one of my projects. It allowed me to paint a broad range of topics, from underwater scenes to waves, to ocean sunsets, to shells, to sea creatures.

illustellar 100 Day Creative Project

Choose two or three parameters that will guide you and leave a lot of room for creative expression. You can decide to stick to one medium only (watercolors, digital painting, line drawing, pastels, or paper cutouts). You can restrict your color palette or size of your paintings.


When I came up with my “100 Days of Nature, Honey” project, I wanted to explore watercolors. Also, I was obsessed with hexagons at the time. So I decided to create 100 hexagonal paintings, all nature-inspired, using watercolors and masking tape. The direction was clear, but I had a lot of freedom, and my creativity exploded with this one. I continued way beyond 100 days and expanded to other canvas shapes, with hexagonal motifs still baked into my paintings.

illustellar 100 Day Creative Project



If after a while you’ll realize you’re feeling stuck and you don’t like the parameters you’ve chosen for your challenge, modify them. It’s your project!




As I’ve mentioned before, taking the time to actually learn during such a project is crucial. When the pressure to churn out finished pieces every day is off, you can allocate part of that time to watch YouTube tutorials or online classes. Actively seek new tips and tricks to implement in your work. Learning inspires creativity. Even though you’ll amass fewer finished pieces in the end, you’ll progress faster.




Let’s say you’re reading this article in April. You might be thinking about tackling such a challenge next year. Or you may regret you haven’t thought about starting a yearly project this year. Well, guess what? You still can.


Don’t let the “magical” January 1st threshold dictate your life! You don’t have to postpone your creative plans for several months just to fit into the calendar. That’s ridiculous. When you’re ready, you’re ready. It’s 365 days in a row, regardless of the actual date. Sure, maybe it won’t look so glamorous when you start on random Tuesday in August. Perhaps you won’t feel this New Year’s resolutions buzz we’re all addicted to. But ultimately, it doesn’t matter. You have one life only. Make the most of it, and start your creative journey today.