Challenge Yourself

I was browsing about online and I came across this motivational message about constantly challenging ourselves. Sounds good, doesn’t it? A bit more browsing brought up reminders of how we grow when challenged, not when things are easy. I found many references to “challenging our limits” rather than “limiting our challenges.”

Good advice, sure. But I’m here today to call it into question. I’m not sure we gain all that much by constantly challenging ourselves, especially where art and creativity are involved. Pushing too hard, taking on too many challenges, and pressuring ourselves too much can sometimes have less than desirable outcomes. The qualify of our art can suffer if we’re rushing to keep up, if we’re feeling obligated to turn in “an assigned piece” each day, or if we’re struggling to find ideas — all of which often happen when we take on a specific challenge.

The art world is filled with challenges. Some — like Inktober and World Watercolor Month — have been around for a long time and have become well-established events on our creative calendars. Another popular challenge is the 30×30 Direct Watercolor Challenge which was on-going throughout the month of June. In addition you’ll find many other challenges coming and going at different times of the year. If you’d like a quick look at what you can find online, check out the post I wrote a couple years ago:

Ready for a Challenge?

Challenges can be good. My purpose here is not to dissuade anyone from taking on a challenge, but to help us find the right challenges, to make us each better prepared for those we choose to join, and to share a few thoughts about my personal experiences with different challenges over the years.

Since I began pursuing my interest in art six years ago, I have participated in several Inktober challenges, done the Doodlewash “World Watercolor Month” challenge, tried the Direct Watercolor challenge, and have signed up for the 100-Day Creative Challenge more than once. I’ve also put together a challenge of my own, completing a series of 31 Index Card Oil Paintings last December.

So, let’s cut to the chase here. Which challenge have I most enjoyed? Without a doubt, my personal 31-Day Challenge. I’ve also enjoyed the 100-Day Creative Challenges I’ve done.

All challenges, I think, begin with a common overall objective: to help us improve our art skills. Secondary objectives include creating a daily art habit — which is always beneficial — and providing creative inspiration. Most of these challenges advocate sharing, so we have opportunities to get acquainted with other artists, to see their work, to learn from them, and to offer encouragement as well.

With an online art challenge such as those I’ve mentioned, nothing is mandatory. You can sign up for a challenge and, if you decide it’s not right for you, you can walk away from it. Of course, doing that can leave us feeling that we’ve failed, that we haven’t been able to live up to expectations. Those are not good feelings to deal with.

On the other hand, there’s nothing quite like successfully finishing an art challenge. I still delight in looking back to Inktober 2019, going through the 33 drawings I made, and remembering how much I enjoyed my daily drawing time. In the same way, I sometimes look back at those 100-day challenges and at my personal 31-Day Challenge, always feeling a genuine sense of accomplishment.

This is how a challenge should be. Along with that satisfying feeling of completing a project, there should also be indications that our art has improved. After all, isn’t that really why we’re getting involved in the challenge? If we’re not learning and growing, then maybe the challenge isn’t right for us. On the other hand, if a challenge is too difficult for us — such as the 30 x 30 Direct Watercolor Challenge was for me last year — we’re not really going to benefit from it, and consequently, we’re not really going to enjoy it, either.

On the downside of art challenges, we find issues about making time. How do we fit this daily challenge into our schedule? Do we keep up day by day or do we try to play catch-up on the weekend? And if we do fall behind schedule, is that going to upset us? What if life intervenes and we have to set the project aside for a while — or give it up altogether? Good art challenges bolster our confidence, not make us feel harried and pressured.

Another question involves subject matter. What are we supposed to draw each day? What if we run out of ideas? To give us a bit of inspiration, most challenges include “prompt lists” with suggestions. You can follow the prompts or not. Good idea, but sometimes it’s not enough. More than once I’ve racked my brain over an idea, wondering what I could possibly draw that might fit a prompt word. It’s especially challenging for newer artists like me who might be able to envision what we want to draw but find our skills a bit lacking. With my earliest attempts at Inktober, for example, I tried following prompts, always thinking “What’s the easiest way I can express this idea?”

Of course, we’re each different. We each have different skill levels, and we each have different needs, therefore we each have different reasons for accepting or declining a challenge. Maybe what you enjoy most is the feeling of community and the opportunities for new friendships. Or maybe you’re most concerned about having a limited amount of time to devote to a challenge. Whatever it is we’re looking for, we can probably find it in a challenge — if we take the time to figure out what we need and why.

  • If you’re an accomplished artist and you’re looking for an enjoyable way to make new connections with other artists, then you’ll probably do well and enjoy any art challenge you choose, especially if it involves a medium you like using.
  • If you’re an intermediate-level artist looking to improve your skills, try challenges that focus on quantity, such as the 100 Heads Drawing Challenge. You can also create a personal challenge — drawing 100 figures, drawing 100 animals, drawing… anything. Decide what area you want to improve and go for it. For me, with the Inktober 2019 challenge, I wanted to improve my ability to draw trees. Over the course of 31 days (and 33 drawings) I feel I did exactly that.
  • If you’re a beginning artist, go easy on the challenges and just let yourself have fun with it. I completed World Watercolor Month in July 2016 as I was just starting to learn watercolors. I didn’t turn out any great paintings, but I enjoyed playing with my watercolors each day.

What matters most to me in a challenge now is that I have an opportunity to learn something, not just practice drawing or painting. This is why I’ve enjoyed the 100-Day Creative Projects. There are no set rules about what you can do. It’s all personal choice, and that choice can involve any creative activity or learning experience. Both times I’ve participated, I’ve chosen to spend 100 days reading and studying an art book, and I feel I’ve learned a lot from the experiences. I did it first with a book on watercolor and most recently with a book on adding mood and atmosphere in oil paintings.

Another important thing for me is being prepared and knowing what I’m going to do each day. With Inktober 2019, I sat down a month ahead of time (when the new prompt list was released) and made a list of the different tree species I would draw each day. I had so much fun! I learned a lot about trees, too. When Inktober rolled around, I was eager, excited, and ready to go.

In the same way, my 100-Day Creative Projects have had a simple, straight-forward “what to do” each day included. Each time, I’ve gone through the book ahead of time and made out a 100-day “schedule” so that on any given day I would know exactly what to read and do.

With my personal 31-Day project of 3 x 5 card landscape paintings, I prepared in advance by choosing 31 tonalist paintings I would use as inspiration. I never had that awful sensation of “Oh, my, what am I going to do today?” I knew ahead of time, and so I looked forward to coming to the studio each morning and getting right to work.

From my personal experience, I’ll also offer a few “don’t do” suggestions:

  • Don’t take on a challenge you know you’re not ready for.
  • Be realistic about your time commitments. If you can’t comfortably fit an art challenge into your schedule, decline it.
  • Don’t accept a challenge just because your friends are doing it. If it’s right for you, fine. If not, don’t do it.
  • Don’t choose a challenge you know you won’t enjoy. If ink drawing isn’t your thing, please, don’t try Inktober. Not into direct watercolor? Skip that one, too. Does the idea of drawing the human head give you panic attacks? Trying to do it 100 times probably won’t be a pleasant experience. In other words, use your common sense. Choose challenges that use your favorite media or which focus on your favorite subject.

For me, it seems the best challenges are self-directed ones. I get to choose the media I’ll be using. I determine the time-frame. I set all the parameters. This, I think, plays to some of my natural strengths. I’m self-motivated, I’m interested in learning new things, and I’m reasonably good at finding resources I need and teaching myself. This also allows me to work at my own pace without an online community pushing or prodding me to keep up.

Personal projects, however, don’t work for everyone. It can be easy to give up on a personal project. After all, no one is there to hold us accountable, right? Sometimes personal projects fall by the wayside, too, because we don’t have the knowledge we need and we’re not sure where to find it. Sometimes, if we’re not clear on our objectives, we might also set a personal project aside because we can’t be sure we’re making any progress.

So, if you want to do a personal project, be specific. Choose exactly how long the project will last, know exactly what you want to accomplish, have a plan on how you’ll achieve your goal, and make sure you have the time and materials you need.

In conclusion, let me return to that first bold statement. Do we really need to challenge ourselves constantly? No, I don’t think so. That advice, by the way, was for a physical work-out program. Art is a lot different. It’s not about repetitions, distance run, or weight lifted. Maybe we can push ourselves a bit in different areas, but constant challenges will just wear us down. This is why it’s important for us to understand how challenges differ, how they can benefit us (or not), and how we can choose the challenge that’s right for us.






  1. I haven’t taken part in any challenges. In the rather short time I’ve been pursuing my art interests, I’ve literally been busy in art constantly: learning, practicing, reading books and articles, following along with videos or online classes, looking at the world of art out on the web, going to my local art center’s gallery. I paint, sketch, do fiber arts or other mixed media. I printed off a page of prompts for abstract painting once but haven’t needed to use it. I can’t keep up with the ideas in my head, so I’ve created a system that will prop me up if ever that block shows up: I sketch a lot, at least 5 nights a week. I’m just learning but I practice and practice and add to my learning gradually. I enlarge the sketches I’m proud of, print them off on multimedia paper and stash them away in a pile. When I’m not doing other projects, I grab one of those sketches and paint it. I also have large projects started and stashed in that pile, waiting to be continued when I’m more capable. I feel I’ve created an ongoing, self-directed challenge for myself. And I paint most days every week. I know I would stress out and totally miss any benefit of a community challenge; although it would be nice to meet more artists online.

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    1. I love your approach to art. I truly think our “self-directed” challenges are the best because we know instinctively what we need, and working with an “organized challenge event” doesn’t always provide real inspiration. Another drawback to art challenges that I didn’t mention is the problem of comparison. With Inktober, as an example, I was always visiting other blogs, looking at what other artists had done, and feeling that my drawings were inadequate by comparison — at least the first few times I did the challenge. In 2019, I knew what I wanted to do, how I was going to do it, and it was a great success for me. So, I guess what I did was to take an existing challenge and “re-write it” to fit my own needs. Personal challenges are really the best for me, and for you, as well, it seems.

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      1. Maybe I’ll try one/some in the future. I did go to a life/drawing class. Couldn’t even have imagined that just one year ago. It was fun. I did put one of my drawings on the table at the end of the event as everyone else did. Very clear that I was THE total newbie. I was a little embarrassed but also proud of myself for having tried. Can’t compare to them; have to compare my progress against myself. (So easy to say; harder to do.) 😊

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  2. I’ve started using challenges, particularly the ones with prompts, as conceptualization challenges; I’ve found that attempting anything resembling a complete work of art on a predetermined schedule (especially daily, as so many of these challenges are) to be awfully stressful, but taking each prompt and doing a quick concept sketch that I can then put aside for later is a lot more useful. This is especially true as I tend to be very “samey” in the subject matter I draw, and the challenge force me to branch out a bit; without the expectation of completing a work during the challenge, I can sit and sketch and conceptualize more out-of-the-ordinary ideas. I did that for The A-to-Z Challenge this year, and most of my sketches were, uh, really rough (like, a step above stick figures, and often with marginalia where I fully wrote out key words or ideas instead of drawing them). But I’ve revisited two of them already (my goal is to revisit at least five) and I’ve worked on them as I would work on any other project, and they have turned out decently. I think you need to decide what you want to get out of a challenge and participate within that spirit, even if it’s outside the letter of the law, so to speak.


    1. What an awesome idea! That’s a great way to make the most of a challenge. You’ve inspired me to look at those prompt lists from a new perspective. Thanks so much for sharing your thoughts.


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