Category: Painting

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The characteristics the successful ones had in common

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. A 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. A 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. A 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. A 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.

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.

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.

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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.

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A combined writing/drawing challenge may be just what you need.

I’ve been working on a fantasy novel for a couple of years now, and I tend to work on it in sprints between other, shorter projects.

In December 2022, I cleared my schedule to work on my novel for a month. I was on my second draft and I hadn’t looked at it for a few months, which made the prospect of starting up again intimidating.

After pondering over my next course of action, I arrived at my favorite solution to creative blocks: an art challenge.

I decided that, for the month of December, I would do at least one of three activities every day: draw, write my novel, or prepare to write my novel (e.g. plotting, world-building, etc.). In effect, I mashed together Inktober, Preptober, and NaNoWriMo, with a bit of flexibility to choose between them day-to-day.

I also made intermittent updates on YouTube along the way.

Looking back, it was one of the most successful of my self-imposed creative challenges. I made huge leaps in clarity about my novel and kicked off some writing momentum that lasted for months afterward.

Writing and art go well together

I mostly drew on days when I was stuck in my novel. The main difficulty I had was in engaging my visual imagination for descriptions.

It’s easier for me to develop visuals through drawing, and then describe in words from there, rather than try to go straight from imagination to words.

Switching back and forth between writing and drawing was helpful in other ways, like in managing my energy and a sense of continuity. I frequently need to rest the verbal part of my brain, and it was nice to be able to do that while still steeping my imagination in my fictional world.

The practice developed my art skills.

Even though I chose to write rather than draw on most days, I still got more art practice than in an ordinary month.

Generally, the biggest obstacle to sitting down and drawing is deciding on a subject. In this case, the subjects were dictated by the needs of my writing, so I could get into the art straightaway without having to make too many decisions.

That’s a lesson I’ve taken away from this experience: for art challenges, it’s worth taking the time to pre-decide what subjects to draw. It makes executing the project much easier on busy days.

As I write this, it occurs to me that one could use other types of writing projects to a similar advantage, for example, illustrating a month’s worth of blog posts could be a good theme for an art challenge. (If you are some type of writer, how would you adapt this approach to your needs?)

The result of all this practice was to clarify my illustration process and style (for this particular type of fantasy illustration), which I will go into a bit more in the next section.

Illustration process

For the artists reading this, the process I used may be of interest, so I will share a few notes here.

• These illustrations were done in Procreate on an iPad, but the process is similar if you use Photoshop or Clip Studio.
• I used a few reference photos including pictures I’d taken on vacation and images I looked up of cliff dwellings from around the world.
• I started each drawing from a template file with all the layers I need already set up. I got the idea to make the template from this video by LavenderTowne. The important layers are named (from the bottom) Sketch, Flat, Color (which is set to ‘clipping mask’), Shading (which is a multiply layer set to ‘clipping mask’), and Ink.
• First I sketched roughly on the Sketch layer, and when I was happy with it, I jumped up to the Ink layer and made cleaner line art. Then I used the select tool on the Ink layer and filled the selection on the Flat layer. (If you’re wondering what ‘flat’ means here, this tutorial might help.) Then I colored and shaded with the brush tool on the respective layers.

After the basic steps, I usually ended up adding some extra layers (set as overlay layers) for fun, atmospheric light effects. I’d brush on a variety of colors, erase swirls out of them, and smudge them around to act like sunlight.

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Having done a few of these art challenges, I’ve learned that the longer the challenge, the more flexible it has to be. I chose to make this a month-long, so I left room in the parameters to adapt to the needs of my project.

I knew this format suited me because it let me build momentum.

Best of all, I reached the end with some energy left in the bank, ready to keep up the writing habit for several more months. (I only stopped when I ran into a new obstacle in my novel, which I’m going to try to tackle now with, you guessed it! Another art challenge.)

This was my second art challenge (first one here), and the one that convinced me that I’d keep doing this style of project whenever I could.

If you’d like to read more about this project, you can read/watch all the updates I made along the way!

Originally appeared in Share Your Creativity