How to Get the Most Out of a Daily Drawing Challenge

How to Get the Most Out of a Daily Drawing Challenge

A few years back I had been working on RetroSupply so much that I completely stopped drawing. Every time I sat down to work on an illustration I was frustrated and overwhelmed.

    • What should I draw?
    • Should I make a personal project like my favorite artist?
    • What if I finally follow along with that drawing book I got five months ago?

Before I had even started I was overwhelmed by decisions. This was the #1 thing that stopped my from every making progress.

Then one day while talking to my friends someone suggested I draw a picture and post it every day for 100 days. I committed and started the challenge the next day.

Between the social pressure and the clear simplicity of the challenge I was able to do it! I drew for 100 days straight and by the end of the challenge the quality of my work had improved, I was faster, and I felt great.

We created the Fright-Fall Drawing Challenge as a way to help you improve your drawing skills (and have some fun in the process). If you haven't signed up yet, you can sign up for the Fright-Fall Drawing Challenge here.

In this blog post, I'll give you 7 tips and one bonus that will help you get the most out of Fright-Fall Drawing Challenge (or any drawing challenge) and preserve your sanity.

Drawing Challenge | Set a goal

1. Set a Goal for the Drawing Challenge

After the excitement of the first few days of the drawing challenge your daily drawings will start to feel difficult. This is what Steven Pressfield calls the resistance in The War of Art.

“Resistance is experienced as fear; the degree of fear equates to the strength of Resistance. Therefore the more fear we feel about a specific enterprise, the more certain we can be that that enterprise is important to us and to the growth of our soul. That's why we feel so much Resistance. If it meant nothing to us, there'd be no Resistance.”

- Steven Pressfield, The War of Art

The punch the resistance in the face, try setting small achievable goals. These will keep the project from becoming blurry and overwhelming and keep you motivated, for example:

  • "I will only use one line brush and one filler brush to eliminate unnecessary decisions."
  • "I will only draw the actual drawing prompt. Not backgrounds."
  • "I will post Monday - Friday because I know I need my weekends to rest and refill my creativity."

2. Be Prepared to Mess Things Up

It feels great when we first start a drawing challenge. Everything is perfect — the possibilities are endless!

But it doesn't take long before we mess something up.

  • We miss a day (or two)
  • A drawing looks embarrassingly bad
  • We rush a drawing and it doesn't match the rest

It hurts a little when we inevitably mess things up. But it's also a sign of success. Messing up means we faced the resistance, we showed up, and we pushed through. That's what artists like us do; they ship stuff. Even on the bad days.

Expect that you will mess up. That is often when you are growing most!

Drawing Challenge | Hard days are part of the process

3. Don't Compare Yourself To Other Artists

“Comparison is the death of joy.”

Mark Twain

Judging your work based on someone else is a recipe for feeling bad. Everyone is on a different journey. Some folks can spend all day drawing. Others might only have 15 minutes each evening. One person may focus all their free time on drawing while another has many interests they're pursuing.

Compare yourself to who you were yesterday, not to someone running a different race.

Looking for a Daily Drawing Challenge?

Fright-Fall is a drawing challenge from RetroSupply that happens the entire month of October. It includes 31 daily prompts, a free set of digital brushes to use during the challenge, free prizes, and the chance to win an iPad Pro!

4. Practice Self-Care During a Drawing Challenge

A drawing challenge should push you a little bit. That's how we improve. But a drawing challenge should not have your curled up in the fetal position rocking back and forth.

If you feel completely overwhelmed or frustrated stop and take some time to take care of yourself. Here are some ways you can avoid burnout during a drawing challenge.

  • Do a 10 minute meditation on Headspace (trust me, it will be 10 minutes that pay you back with interest).
  • Consider putting limitations on the drawings so they don't become huge projects (see tip #1).
  • Set a specific number of vacation days that you can simply skip on drawing and relax.

Pushing yourself should help you improve, not break you.

5. Use Inspiration and Reference Images

One of the best ways to prepare for drawing every day is by getting your hands on some drawing prompts, inspiration images, and drawing reference material.

If you're doing the Fright-Fall Drawing Challenge, be sure to review the drawing prompts a few times before the challenge starts so your subconscious mind can work on ideas.

Consider making an inspiration and reference image file in advance so you can quickly get inspired for each drawing prompt.

Here are some of our favorite ways to organize images for inspiration and reference:



Drawing Challenge | Save time by making thumbnails

6. Save Time by Making Thumbnails

Ever have trouble getting started with a drawing? Eliminate art block by drawing thumbnails for your weekly drawings in advance. Make them simple and messy. Just having a simple thumbnail ready will help you to get into the flow faster.

Some of our favorite places to draw thumbnails include:

7. Starting Early Is Okay

There's a lot to draw, and drawing daily means you have less time for other tasks. Consider making some of your drawings before the challenge starts. Or, if you're having a productive drawing session, do more than one prompt. This buffer will be helpful when unexpected obligations pop up or if you have a hard day.

[BONus TIP] Set-Up a Drawing Assembly Line

A drawing assembly line is a system you create to minimize friction and eliminate repetitive tasks. Your goal is to make it as easy as possible to go to your workspace, start drawing, and post your work.

Here are some ideas for creating a drawing assembly line:

  • Have all of your drawing materials ready to go each day.
  • Save a template in your preferred software (if you're using software).
  • Print and post the drawing calendar for quick reference.
  • Bookmark your inspiration and reference board to eliminate searching.
  • Keep a document with hashtags. If you're participating in Fright-Fall be sure to use hashtags #frightfall2021 and #retrosupply each day.

Conclusion: How to Prepare for a Drawing Challenge

A daily drawing challenge should help you improve as an artist, meet friends, and have a good time. A little bit of preparation, reasonable expectations, and flexibility will go a long way in getting the most out of the event.

What tips for preparing for a successful drawing challenge did I miss? Let me know in the comments!