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.

1. Set a Goal for the Drawing Challenge

Starting a drawing challenge is exciting, but after a few days, the enthusiasm may wane. Steven Pressfield refers to this as facing "resistance" in his book, The War of Art. This resistance often manifests as fear, and it's usually a sign that the challenge is important to you.

To push past this resistance, set specific, achievable goals. For instance:

• • Use only one line brush and one filler brush to simplify choices.
  • Focus on drawing only the prompt, avoiding backgrounds.
  • Commit to posting from Monday to Friday, reserving weekends for rest.

By narrowing your focus, you’ll make the challenge more manageable and stay motivated.

2. Be Prepared to Mess Things Up

Starting a drawing challenge is invigorating, and it’s easy to be enamored by the endless creative possibilities. However, mistakes and setbacks are inevitable:

• • Missing a day or two
  • Creating a less-than-perfect drawing
  • Rushing and producing inconsistent work

While these errors can be disheartening, they're also indicators of progress. Each hiccup shows you've confronted resistance, remained committed, and pushed your boundaries. In the creative journey, stumbling blocks often become stepping stones for growth. So anticipate setbacks, and recognize them as valuable learning moments.

3. Don't Compare Yourself To Other Artists

Mark Twain once said, "Comparison is the death of joy," and it holds true in the world of art. Comparing your work to others is a surefire way to dampen your enthusiasm. Artists are on diverse paths: some may have entire days to dedicate to drawing, while others may only find 15-minute pockets of time.

Instead of measuring your work against someone else's, focus on your own progress. Aim to be better than you were yesterday, rather than competing with someone on a completely different journey.

4. Balance Ambition with Self-Care

While a drawing challenge should stretch your abilities, it shouldn't push you to the point of emotional or mental strain. If you find yourself overwhelmed or frustrated, it's crucial to pause and recharge.

Here are some pragmatic ways to prevent burnout:

• • Take a 10-minute meditation break; it’s a small investment for substantial mental clarity.
  • Impose limits on your projects to keep them manageable (as recommended in Tip #1).
  • Allocate a specific number of "off-days" where drawing is optional, allowing you to relax.

The aim is improvement, not exhaustion. Setting boundaries allows you to challenge yourself effectively without jeopardizing your well-being.

5. Arm Yourself with References and Inspiration

Being well-prepared can make your daily drawing challenge much more rewarding. To set yourself up for success, gather drawing prompts, inspirational images, and reference material in advance.

For example, if you're participating in the Fright-Fall Drawing Challenge, familiarize yourself with the prompts beforehand. This allows your subconscious to start generating ideas even before you begin.

Create a dedicated folder for inspiration and reference images. Having this at your fingertips can make each daily prompt an opportunity for creativity rather than a hurdle to clear.

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

• • Pinterest
  • Apple Photos
  • Evernote
  • Dropbox
  • Google Photo

6. Streamline Your Process with THumbnails

Many artists struggle with "art block," that moment when staring at a blank canvas feels overwhelming. One effective strategy to counter this is to create thumbnails for your weekly drawings ahead of time. These aren’t meant to be detailed or polished; think of them as the rough sketches that serve as your creative springboard.

Creating thumbnails offers several advantages:

• • Quick Start. Having a thumbnail ready eliminates the paralysis of a blank canvas, allowing you to dive into the creative process more easily.
  • Planning. Thumbnails provide a visual roadmap, helping you allocate time and resources for each drawing.
  • Flexibility. They can be revised or adapted as new inspiration strikes, giving you a balance between structure and spontaneity.

By incorporating thumbnails into your routine, you not only save time but also create a conducive environment for your creativity to flourish.

7. Build a Buffer by Starting Early or Doubling Up

Committing to a daily drawing challenge can be time-consuming, leaving you with less room to tackle other responsibilities. One way to ease this constraint is by building a buffer—either by starting your drawings before the official launch of the challenge or by completing multiple prompts in a single, productive session.

Expanding on the benefits:

• • Reduced Stress. Having a few drawings in your buffer can lessen the anxiety that comes with daily deadlines.
  • Flexibility. A buffer provides a safety net for those days when life gets in the way, or when you're simply not feeling inspired.
  • Momentum. Doing more than one drawing during a burst of creativity can give you a sense of accomplishment that fuels future endeavors.

Creating a buffer isn't cheating; it's strategic planning. It affords you the latitude to fully engage in the challenge without sacrificing quality or missing out on life’s other obligations.

[BONus TIP] Optimize Your Workflow with a Drawing Assembly Line

In any creative endeavor, efficiency is key. A drawing assembly line is a set of pre-established processes that helps to minimize friction and repetitive tasks. By setting up such a system, you streamline the journey from idea to finished artwork, making it far easier to stick to your daily commitment.

Here’s how to create an effective drawing assembly line:

• • Materials at Hand. Ensure all your drawing supplies are ready and within reach to minimize setup time.

  • Templates. Save templates in your software of choice for consistent sizing and formatting, speeding up your initial steps.

  • Calendar and Prompts. Print out the drawing calendar and keep it visible for quick reference, so you're always aware of upcoming prompts.

  • Bookmark Boards. Keep your inspiration and reference boards bookmarked to save time searching for ideas.

  • Hashtag Document. Maintain a document with relevant hashtags, making it quick and easy to post your work. For example, if you're participating in the Fright-Fall challenge, have hashtags like #frightfall2023 and #retrosupply ready for each post.

In essence, a drawing assembly line serves as your creative conveyor belt, automating the mundane tasks and letting you focus on the art itself.

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!