Category: Essays

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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

An odd project sprouts

One afternoon, I reached into my spice cupboard to find that one clove in the bulb of garlic I’d forgotten had grown a bright green sprout.

I planted it to grow as microgreens. According to a friend who knows these things, the correct way to plant it is actually to separate all the cloves and put them in a dish of water. Even with my inexpert planting in soil, each clove shot up a shoot, just like the first. I nibbled off the flavorful tips.

For several days, I had been prowling the house, ambushing each houseplant for a portrait. As well as the occasional outdoor plant or vegetable. It was an art challenge I’d set myself.

I call them ‘portraits’ because I was determined that the plants be represented in detail, as a subject. They would not be simplified into an artful tangle of foliage, as one does in landscape painting. I would draw every leaf and branch.

The garlic plant featured late in the challenge because it had more leaves than some others. I waited for a day when I had time to do them all justice.

At first, capturing all the detail seemed insurmountable. The leaves passed behind each other, casting sharp shadows from the afternoon glare from the window.

From doing these drawings a few days in a row, I knew that sense of impossible complexity would pass. I just had to pick a leaf and go from there, and remind myself that this had worked last time.

Even shapes that look too difficult to draw can be tackled, one nibble at a time.

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

Originally appeared in Weeds & Wildflowers

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My 10-day digital line art challenge

I was craving art time after a particularly busy (and analytical) period, so I decided I’d make digital plant art for 10 days in a row.

When I made the decision, I’d already been drawing a few plants in the style I planned. The change would be to do the drawings consecutively, as part of a 10-day challenge.

Additionally, I would screen-record my drawing process and post it on YouTube each day. So, this 10-day challenge was also the launch of my YouTube channel.

I jumped in without too much planning, beyond shelving my other projects to make time, and looking around to make sure I had approximately 10 plants available to draw.

From there, I basically took it day by day.

Looking back, it was a decided success! Here are the 10 awesome things that came from it.

1. I was able to quickly develop and hone a new art style

When I started this challenge, I had just begun experimenting with a new vector line art style* that was quite different from any of my past work. I was excited to see where I could take it.

By drawing in this style for 10 days in a row, I was able to improve on it from day to day, and let it sink into muscle memory.

Since doing the challenge, the style has become one of my staples for digital art. I can now dip back into it easily because it’s so well-practiced.

* In the iPad app, Vectornator. My review of the app is that it’s pretty decent and I continue to use it. Sometimes their updates make features worse. But I still enjoy the core functionality and feel of the lines. (Not sponsored.)

2. I learned what it’s like to satisfy the art craving

Generally, it’s hard for me to find enough time to do all the art I want to do, between my other projects and hobbies. I usually cycle between projects, making sure to come back to art often enough to feel balanced.

Even so, I frequently end an art session wishing I could do more, but other projects demand my attention.

In contrast, these 10 days of drawing were just the right amount of art-time. I wasn’t sick of drawing at the end, just pleasantly tired and pleased with all the work I’d done.

The experience showed me what it was like to fully satisfy the art craving when it arises, and to move onto other pursuits not because I have to, but because I’m actually in the mood to.

Now, I know what to aim for when I make space in my schedule for an art series. There is such a thing as ‘enough’ art time! (Until the next craving, of course.)

3. I got a clearer intuition on how long an illustration takes

Along the lines of the previous point, it’s hard to anticipate how long a drawing will take, and that can be a barrier to getting started.

I don’t have a great sense of time in general, and I lose track of the clock completely when I’m absorbed in art work.

Since this challenge involved screen-recording myself drawing, I could just look back at the video length to know how long it took. And since I did that for 10 days in a row, I got a sense of the average time I need to finish an illustration. It came out to 40–50 minutes for this type of illustration.

Having this foreknowledge meant I could start a drawing even in the middle of the day, with a full schedule ahead. It’s safer to dive into an art session with the reassurance that you will resurface within an hour!

4. I completed a cohesive illustration series in a short time

After the 10 days, it was satisfying to look back on the series of drawings I’d made. Better still, I could now use them in my other content.

In the months after the challenge,

• I used my drawings as feature images in blog posts.
• I turned a few of them into wall art for my apartment.
• I put them in my portfolio and in galleries on my website.
• I offered them to subscribers as a freebie in the form of an art book.

I can do that with any of my art, of course. But for me, this was an unusually rapid and efficient way to make an illustration series.

5. I got over the hump of setting up my YouTube channel

I’d been meaning to make a YouTube channel for a while, but this challenge (and the excitement on the first day) got me over the hump of setting it up.

On Day 1, I got my personal YouTube channel ready for the public by deleting old comments, archiving old videos, adding a profile photo, etc. None of this took long, and I didn’t overthink it because I was eager to get to the drawing challenge.

I also raced through the set-up steps of making the videos. I installed video editing software, made (rather bad) title cards, and collected royalty-free music to use in record time.

The process of editing and uploading videos felt unfamiliar and difficult on the first day, but by day 4, it was a piece of cake. Cramming the learning curve into a short time made it easier to get past.

I also learned, for future reference, that it takes me about an hour to edit and publish these videos.

6. I solidified my YouTube channel’s niche and tone

The tone, music, and visuals I chose for my plant videos were quite different from my other platforms — lighter and more cheerful. It felt odd and unlike me at first, but much less so by the last day!

I was able to confirm that — yes, I do like posting this type of video (called ‘speedpaints’), and I’d like to continue to go in that direction.

And I got past the stage of having an empty-looking channel. With 10 videos on there, it looked mature and ready to show to people.

7. I felt like I was really seeing my plants for the first time

Something happens to me when I draw consistently. It changes the way I see. Colors and details pop more, and I appreciate more of the beauty around me.

That goes double for when I draw nature, by deepening my connection to the Earth and living things.

I’m often grumpy when I can’t get out to natural spaces for hikes. Looking carefully at the plants near me was a good reminder that you’re never cut off from nature, even indoors, if you look for it.

I ended the challenge feeling much calmer and appreciative of my surroundings. Even in the mood to try some interior decorating.

8. I learned about how I like to work

The success of this project got me thinking about structure — how much I need, and how much is too much.

In the past, I’ve worked completely free-form, with hardly any structure at all. I thought this is what I preferred. But it made it hard to finish things, which was frustrating.

At other times, when I’ve tried to create rigid daily habits or follow public challenges like NaNoWriMo, the structure completely cramped my style.

I need to be able to flow between projects (and areas) according to my natural rhythm. That means, if I’m going to do the same activity every day, it needs to be for a short time.

For a lot of people, 10 days isn’t a long challenge. Thirty or hundred-day challenges are more common. But for me, it was the perfect length.

This challenge demonstrated that I can create structures that support my particular work style.

9. I gained insights about 10-day challenges, specifically

This wasn’t my first 10-day challenge, but it was my first successful one. There are a few things I did differently this time that made it work, and convinced me to keep using this format in future.

The first thing was that I didn’t just draw everyday — I published every day. Each day of the challenge created a completed piece, and there was no follow up needed.

In the first 10-day challenge I did, I wrote a response to a writing prompt every day, but I didn’t publish. While I did succeed at keeping it up for 10 days and I got a lot of writing practice, I still haven’t edited and published any of those pieces, as of time of writing. It’s been over two years since I did that challenge.

In contrast, this time around, when I got to the end of the 10 days, I was done. I’d succeeded. There was nothing more needed to complete the project.

That was important, because I was tired and ready to do something new! I didn’t want the challenge to create more work for myself at the end.

Also, by repeating the full publishing process so many times in a row, I had ingrained every step in memory. Even now, I am comfortable making a full video in a few hours because of all the practice.

10. I built confidence in my ability to follow through

Until the last day of the challenge, I was in suspense as to whether I’d actually do 10 consecutive days! When I got to the end with an unbroken streak, it was a huge confidence boost.

As I’ve mentioned, structured projects haven’t always gone well for me. And even when I do finish them as planned, they don’t always have the effect I hoped for.

Not so with this one!

I’d learned a new skill, launched a YouTube channel, and done what I said I’d do.

All reasons to believe I could do it again!

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So, those were the 10 amazing things that happened when I drew plants for 10 days in a row.

If you are thinking of doing a self-imposed creative challenge, I can’t recommend it enough. Remember to tailor it to your particular work style, and make it just difficult enough to be exciting! I find that even a challenge that doesn’t push me to my limits is still helpful, since it provides consistency I don’t otherwise have.

And if you are curious or want to replicate this challenge yourself, you can see all the updates I made along the way here: (beginning, update 1, update 2, gallery, YouTube playlist).

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

Originally posted in Share Your Creativity.