I recently wrapped up my latest personal creative challenge: drawing 300 heads in 30 days in an attempt to improve my portrait drawing skills.
Before you become too impressed by my dedication, let me gently lower your expectations by sharing some examples:
Calling some of these portraits at all is generous.
Could I really expect to get better at drawing if all I had to give some days were some ovals with slight suggestions of facial features?
I did!
Inspired by the ceramics class anecdote that’s crystallized into my brain ever since reading Atomic Habits, I knew that improvement would be a byproduct of sheer volume, even if the individual attempts were wildly uneven.
And this is why I love a creative challenge:
Between careful studies and half-assed hurried scribbles, all of my effort accumulated into meaningful progress.
The challenge worked not because I gave it my best every day, but because I designed it so I didn’t have to.
Designing creative challenges that work on good and bad days has become one of my favorite ways to keep my creative practice alive. If you want to try your own, here are my tips for creating one that works for every version of you!
1. Define your smallest complete rep
One rep should be a miniature, but complete, version of whatever you want to practice. The key is to scale down the process rather than fragment it. In some cases, literally.
For example: instead of “work on a painting for 20 minutes” you may set a goal of “finish one postcard sized painting”. Instead of “write every day” you may “finish one short story”.
Of course this depends on what you want to practice— if you want to improve at drawing eyes, one eye may be a complete rep. For me, eyes were only part of the process.
My rep was drawing an entire head. With each, I went through the same basic steps from beginning to end: observing the reference, constructing the shape, placing the features, adding details and deciding when to be done. The level of time and care for each individual portrait could stretch or shrink, but I went through the same process each time.
Each had a distinct beginning, middle and end, creating a faster and more useful feedback loop.
If you are always starting new pieces but never finishing them, you may get really good at overcoming the blank page but never learn to fix the problems that show up as you work. If you continue on the same piece for days or weeks on end, you delay your opportunity to learn from the culmination all of your decisions together.
The key is to choose something you can finish often, because each ending gives you information to carry in to the next beginning.
2. Choose a finish line
I have assigned myself creative challenges lasting anywhere from one week to an entire year.
I think 1-2 weeks is the sweet spot for trying something new. If you’re already quite invested in a hobby or craft, and know how it fits into your life, then a longer challenge can make more sense.
You can also consider how flexible your challenge is. Portraits are a little too narrow of a scope for me to have wanted to focus on intensely for much more than a month. Even that was a bit long, admittedly. But when I did my 100 paintings in a year challenge, I had enough freedom to follow my whims without being tied to any particular subject matter or style.
There’s also something to be said about the sense of pride and achievement of reaching a finish line. I could have easily set a goal to draw 10 portraits per week indefinitely. But, let’s be real, eventually I’d have a bad day and skip it, and then I’d miss another, and my goal would simply trail off without any celebration or reflection of the effort i did put in.
A finish line makes progress visible, giving you a specific moment to step back and say, “I did it!” You can always continue or try a new, different challenge based on what you learned or a new looming interest.
3. Pick a number that scares you.
This is counterintuitive.
But when it comes to creative work especially, sometimes choosing goals that are too small only creates more pressure. Pressure to make something good, or representative of your best effort. And often, pressure creates avoidance.
If this perfection-based-avoidance does not plague you, maybe you do not need this tip, but it’s something that helps me.
Choose a number that feels slightly unreasonable. Large enough that you cannot possibly give each one your utmost time and attention. It should scare you a little bit but remain technically doable.
For me, that number was 300 portraits. I never had any delusion that I would draw 300 good portraits. 300 meant that each individual portrait meant very little in the grand scheme of the challenge, and helped easy the pressure for each one to be an improvement from the previous or a reflection of my skills overall.
When combined with a solid, complete rep, this allows you to get the most mileage possible from your limited creative time and energy: More chances to practice from beginning to end, learn from the result, and try again.
4. Lower the bar, don’t skip the rep.
A creative challenge that only works under perfect conditions is not particularly useful to me, and it might not be useful to you either.
If my portrait challenge required me to sit down at my desk each night, focused and ready to dedicate hours to optimal practice, I never ever would have finished it. I may have never even started.
I live in the imperfect, so my challenge had to not only work within that realm, but embrace it.
I often drew half-assed portraits sitting at my toddler’s table while preventing him from eating his crayons, half-asleep watching my show, or even in the passenger seat of the car.
You could argue that I probably learned the most on the days that I approached my portraits with attention and focus.
But I would argue that there is an equal amount to be learned from loose, experimental, even half-assed attempts. They helped me overcome the fear of the empty page, draw more intuitively, and stop overthinking each decision.
Making room for playful and imperfect practice was arguably the most important part of this challenge, because it’s what kept me going on the days where the conditions weren’t perfect. Which is, almost every day.
When it comes to creating your own challenge, this means deciding that “ugly” attempts absolutely count, no if ands or buts.
It can also help to decide what a low, medium, and high effort version of a rep might look like in advance, and try to do fit in some of each based on your daily mood and energy. There are no better or worse attempts, just different versions.
Lowering the bar can also mean adjusting your challenge when it’s not serving you. For example, I adjusted my goal from 500 to 300 when I realize the goal I set for myself was truly too unhinged to achieve the right balance of speed and focus. Attaching a set number or frequency is there to support your practice with positive pressure, not create so much rigidity that it takes away your ability to learn, experiment and enjoy.
5. Measure more than finished work
I’m happy to report that my challenge full of imperfect practice did lead to some visual improvement in my portrait drawing abilities.
But, as cliche as it may sound, the greater change is in how I feel. I’ve completely internalized the proportions of the head and can apply them simultaneously without consulting a diagram every 30 seconds. I’m also rarely intimidated to start a new portrait drawing, because I know exactly where to start and what to look for.
Regardless of your challenge, keep in mind that a lot of learning happens off the page. If your goal is improvement, the finished work matters, but it is not the only thing to look at.
Progress is not linear, and paying attention to other measures of success can give you a confidence and evidence that your practice is working, even when the latest results don’t show it.
You might reflect on things like what you can do faster, what you no longer need to look up, what mistakes you recognize sooner, differences in your emotional reactions to “bad” work, and what you are more willing to attempt.
Design your creative challenge:
I have at least one of these creative challenges going on in my life at all times.
And while I fear i’ve simply rebranded SMART goals in a way that feels slightly more adventurous and fun, it works for me!
If you want to use these tips to design your own challenge, here’s a lil’ mad lib-inspired recap:
The point is not to design an ideal challenge and then forgive yourself every time real life interferes. The point is to design it around the life you actually have from the beginning.
Your time, energy, and effort will vary. That is not a flaw the challenge needs to tolerate. It is part of the plan.
Imperfect practice accumulates. Imaginary practice does not.
So please, shamelessly half-ass some art in the spirit of doing what you can.
xoxo,
Rachel