What I Learned from Setting Myself Five Creative Challenges

The characteristics the successful ones had in common

Illustration by the author from challenge #5

In the space of about a year, I set myself five personal creative challenges.

You may have heard of popular challenges like Inktober and NaNoWriMo, where you aim to write or draw every day, or reach a certain word count in a month.

I sensed the excitement around these challenges every year and even participated on rare occasions. I enjoyed it, but the timing and parameters of the challenge never felt right for where I was in my projects.

I’d also taken classes that followed a structure similar to these challenges. I was more successful at completing the classes, and following the structure always paid off enormously in productivity and skill building. Still, I found them taxing and overly restrictive. By the end, my willpower and creative resources were depleted.

Both of these experiences planted the seed that maybe I could design my own challenge, tailored to my goals and work style exactly.

I set myself a ten-day drawing challenge in May 2022, and came away from the experience so delighted that I set myself four more in the year that followed.

Of the five challenges, three were decidedly successful, and two had mixed results. Looking back, I have an inkling of what made the successful challenges work so much better than the others.

Let me share, since my experiences might be helpful in designing your own creative challenges.

The five challenges

Briefly, the five challenges were:

  1. ten-day challenge to make a digital drawing of a houseplant every day, as well as publish a YouTube video of my drawing process every day.
  2. ten-day challenge to write an essay every day around a particular theme (“Adaptation”).
  3. Another ten-day challenge to write an essay every day around a particular theme (“Time”).
  4. month-long challenge to do at least one of three activities (write, plot, or draw concept art for my novel) each day, and publish intermittent YouTube updates.
  5. 7-day challenge to make an illustration around a particular theme (“Recovery”) each day and post it on Tumblr.

Of these, #1, #4 and #5 were resounding successes, because I published a lot and ended up happy and energized.

The essay challenges, #2 and #3, were kind of duds.

Now, I don’t think the issue was that they were essay challenges. I’m confident, now, that I can design an essay challenge that works.

No, the difference was more to do with the challenge parameters.

What makes a successful creative challenge?

After each challenge, I took copious notes, reflecting on the experience. I believe five characteristics of the challenges can help them succeed.

1. The challenge addresses your most important current goal.

Each of my successful challenges was designed around what I wanted most at that moment.

I looked for clever ways to combine all my top goals, like finding time for art and connection to nature, wanting to publish more, and unsticking a big project, into one challenge.

As a result, the challenge was unambiguously my top priority. Working on it was going to get me everything I wanted. (I was constantly reminded of a quote from Mozzie in White Collar: “A true con gets you everything you want.”)

In contrast, the two essay challenges were built on themes that didn’t fall naturally out of my priorities. My goals were to write and publish, and I chose themes that were on my mind, but there was no reason to suppose that exploring them for 10 days would improve my circumstances.

I didn’t have a pressing need for the art I’d assigned myself to make, so I wasn’t as committed to making it. And I had other goals that I had to push aside to work on the challenge.

So, my recommendation is to pick something you want done, are itching to do or even, have already started doing, and turn that into a daily project.

See if you can design the activities of the project so that it simultaneously advances compatible goals like skill-building, having fun, and publishing.

Then build in activities for rest and recovery, or anything else you will need to keep up the momentum.

Creative challenges don’t have to be grand and elaborate; they can be a more consistent version of what you were planning to do anyway.

Illustration by the author from challenge #5

2. The challenge leverages skills you already have.

For two of my successful challenges, I had already started the challenge activity before I decided to make it a challenge.

The 10-day plant drawing challenge started after I’d drawn a few plants and realized I wanted to do more. I already knew how to draw in the style I was planning. I added one (just one!) new skill to practice, which was editing YouTube videos.

In the novel-related writing/drawing challenge, I leaned on the drawing skills I was more confident in to get better at revising my writing.

In both cases, I only needed to spend the first day of the challenge learning the steps of my daily activity. The days after that were spent just repeating the steps I knew how to do.

After the first day, I was honing skills I already had, not acquiring new ones.

3. The challenge closes the loop on each creative piece.

For the successful challenges, I built publishing into the process. I reached the end of the challenge with a stack of complete and already-published materials.

In some cases, I published every day, and in others, intermittently. But in either case, there was no follow-up needed after the challenge was done to get the benefits of all that creative work.

This is where I went wrong with the essay challenges. I couldn’t publish a full essay in a single day (the style of writing I was doing was too ambitious for that), so all I wrote during the challenge were first drafts. To be fair, they were quite good drafts.

But the issue was that I reached the end of the challenge, tired and without having published anything in over a week, and now I had a pile of editing to do.

All the work of the challenge would be for nothing if I didn’t follow up and complete each essay.

This didn’t have the motivating effect I’d hoped for, of looking back on a period of productive work. Even though I was prolific in first drafts, it only meant more work ahead in editing.

So, I recommend designing your challenge so that when you are done, you are done. All the steps of publishing are built into the challenge.

At the end, you have the option to tie your work up with a bow and move on to something else.

4. The longer the challenge is, the more flexibility it needs.

The one challenge I did that was longer than 10 days was also the most flexible. I gave myself the choice to do one of three activities, unlike the shorter challenges where I did the same thing every day.

This was by design.

With challenges like NaNoWriMo, where you do the same activity for 30 days, I found that the work fatigued some parts of my brain. The activities that would help it recover would take time away from the challenge and hence add pressure. This is why I ended these challenges so depleted.

With experimentation, I’ve found that my limit for doing the same activity consecutively is 10 days.

I can maintain a flexible type of continuity for 30 days.

I measure success for the longer challenges in ‘streaks’ (like in Wordle). On a given day, if I do even five minutes of one of the planned activities, I count it as a part of the streak.

Even with this much leeway, the challenge added consistency to my creative practice and kept my project percolating in the background, sparking all kinds of insights. Flexibility doesn’t take away from the project’s effectiveness.

You may not need as much flexibility as I do. You may be able to do the same activity for thirty or even a hundred days straight.

I suggest experimenting and finding a challenge duration that seems almost easy. And the longer you choose to make it, the more choice I would recommend in your activities.

Illustration by the author from challenge #4

5. The challenge is only as difficult as it needs to be.

As I’ve posited in the previous section, a challenge doesn’t have to be a grueling marathon to be worth it. Easy challenges are still beneficial, believe it or not.

The parameters of my challenges aren’t there to make the activities harder. I don’t require myself to work fast, long, or on increasingly difficult tasks. There are no rules against slacking as long as I show up.

The parameters are just intended to produce (a smidge of) consistency.

Within that container, I’m allowed to do anything I want, even to take the easy way out. I find that I rarely do. Once the impediments to getting started are out of the way, I naturally feel drawn to do good work.

This is why I find over-ambitious word count or publishing goals unhelpful. They feel arbitrary and don’t advance the goals I set out the start of the challenge. And they add new ways to fail or fall behind.

The parameters of a good challenge will set you up to feel more encouraged each day than the last. That means finding the process easier and easier with practice, while watching your creative streak grow.

Self-imposed creative challenges are my favorite way to start or unstick a project. Even the ones I deemed less successful led to periods of rapid skill growth.

And the successful ones did that, and more — I created, published, and learned, and kept creating even after the challenge ended because of all the momentum behind me.

It took a lot of experimenting and failing at NaNoWriMo before I found the formula that works for me.

That’s why I recommend tailoring your creative challenge to your unique work style. There is so much upside to be had!

Here’s my worksheet resource for having a deeply creative work session!

Originally appeared in Share Your Creativity.

Leave a Reply

Your email address will not be published. Required fields are marked *