By Jennie Lennick

Art Challenges On Social Media Can Kickstart a New Habit

Daily prompts and social media challenges can help kick start your art practice! Consider participating in an art-making challenge to connect with other artists, gain accountability, try out a new medium, and have fun!  

Starting in 2019, I stitched a small embroidered drawing every day for an entire year. It began as a 100-day project, but I decided to extend it to explore the medium entirely. Every night, I sat down and stitched a small illustration related to something I did that day. I sewed everything from flowers I saw on my walks to meals I prepared. When the pandemic struck, my stitches depicted images inspired by watching Tiger King and a new life indoors.  

I believe making art every day is transformative, and using social media to share your work is a fantastic way to stay motivated. This year, we created a list of drawing prompts as part of Inktober- a yearly drawing challenge in which artists are encouraged to draw every day in October and share their work on Instagram. After the challenge, we asked our artists why they participated and what they learned. 

Have you considered trying a drawing challenge!? Let me convince you to DO IT! 

Share Your Art & Connect With A Community Of Makers

Sometimes it can feel like you’re making art in a bubble. The stereotype of artists sequestered alone in their studios is accurate. Joining in a social media challenge not only invites your friends, family, and following into your practice but connects you with other artists along for the ride.

Image courtesy of Emma Munger.

From illustrator, Emma Munger on why she drew for Inktober:

“I wanted to participate in Inktober this year because it’s a wonderful way to connect with your artist community far and wide. And personally, it also keeps me on my toes and always leads me in a different direction than where I planned to go in the first place. And above all, I just love seeing others’ minds at work on the same prompt- I was wowed by everyone’s pieces this year and so honored to be along for the ride.”  

Gain Accountability to Keep Going

When I did my embroidery project, many friends told me they looked forward to my daily stitches. I felt like if I were to skip a day, I would let my followers down! Putting your work out into the world in real-time is a great motivation to keep making!

Danielle from @sweetheartgrams drew several prompts from our Inktober list.  She reflected, “Honestly, I’m very bad with staying consistent, but I loved the prompts you created, I was eager to work on the next day’s prompt!”

Image courtesy of @sweetheartgrams

Have Fun Making Art! Invite Playfulness Into Your Practice.

Image courtesy of Corey Turner.

Making art doesn’t have to be so serious! Following a list can invite a sense of delight back into your practice.  

From Corey Turner: I loved these prompts because they can be elaborate, simple, or silly. I previously only drew with pen and paper and didn’t use color very much, and this has been a great way to get back into drawing and start incorporating color. It’s been a very fun way to get into drawing digitally also! I guess it’s taught me that it doesn’t have to be intimidating to sit down and draw. I can approach it with a playful mindset and see what happens!

Use The Daily Challenge As an Excuse To Try a New Medium

Have you been wanting to get better at a specific skill, like painting with gouache, drawing with brush pens, or finally mastering procreate? A daily challenge is a great way to practice!  

Illustrator Orlie Kapitulnik, our resident block printing instructor, created a series of rad Risograph prints for every day of our Inktober challenge. 

Orlie stated, “I learned that risograph was a great way to add texture and charm to my daily drawings.”

Image courtesy of Orlie Kapitulnik

It’s fun to try new things, but don’t make it too complicated!  

From artist Chanamon Ratanalert: “I tried to use the challenge as an excuse to try a new medium in video format, trying to abide by Instagram's aLgOriThM’s rules. Still, it ended up being too much for me to do every day. I don’t know how people do it!” 

Casey Moylan used our Inktober challenge prompts to get better at Procreate.  

“I wanted to use Inktober this year to learn more and practice drawing in procreate. It’s a brand new program to me, and I haven’t had a lot of time to play around with it. I’ve still got some days to finish up, but I feel like I’ve accomplished what I set out to, and I can’t wait to keep exploring and drawing more in Procreate!”

Image courtesy of Casey Moylan

Ready to Start Your Project? Here Are Some Tips for Success!

1. Stick to a single medium for the duration of your project

You are already committing to making art every day and have to decide what to make. Make it easier on yourself and eliminate the decision about what medium to use. Plus, using a single medium for the entire project will give all your pieces a uniform look, forming a cohesive body of work by the end of the project. 

2. Keep it simple

There is no way you are going to spend hours a day on your project. Give yourself a time limit to finish your piece- I like to do mine in 15 minutes. Try to complete the art in that time! You may need to simplify your compositions to make them work. 

3. Work small

Don’t try to create a massive work of art every day, or you will set yourself up for failure. Stick to a smaller, more manageable size. All of my daily stitches in my year-long embroidery project were only 3 inches in diameter.

Ready to make art every day?

There are numerous art-making challenges to participate in throughout the year. Some of my favorites include:

Me Made May

Me Made May is a challenge for sewists/knitters/and other garment makers to wear an article of clothing they crafted every day for the month of May. Me-Made-May was started by Zoe of Zo So to connect home sewists and to inspire others to incorporate handmade goods into their daily lives. Check out the hashtag #memademay on Instagram for inspiration!


Jane Parker created Inktober over a decade ago to improve his drawing skills and develop a daily art-making habit. This hugely popular challenge is practiced worldwide throughout the month of October. Check out all the artists who used our Jenny Lemons prompt list at #jennylemonsinktober. You can learn more about inktober here

100 Day Project

The 100 Day Project is a simple challenge in which you choose a creative project in any medium and share the process online for 100 days. I love this challenge because there are no restrictions on the types of projects you can do!  You can sew, cook, sculpt, write, whatever! Just do it every day!  The 100 Day Project officially starts each year on January 1st, but you can do it at any time.  Learn more about the challenge at

Are there any online art challenges you love? Share them in the comments! 

Happy making!


Designer, entrepreneur, and lover of crafts! Boss Lady at Jenny Lemons in San Francisco


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