I started drawing again
On letting go of perfectionism and letting your creativity flow
"I failed bravely!" I declared at the beginning of this month.
Since late last year, I’ve practiced setting new moon intentions — a list of 3-4 things I’d like to embody that are less about achievement and more about leaning into who I am, the good and the bad. Hence, my declaration to fail.
(By the way, reading your intentions in the past tense is just a little trick to get your brain more comfortable with the idea of adopting a change.)
This cycle’s declaration to fail was especially intentional as I set out to do something terribly scary this March: to take up drawing.
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Drawing shouldn’t be scary for anyone, especially for someone like me who took art classes as a kid, who holds a Bachelor of Fine Arts degree, and has centered her career around creativity.
But here’s the lesson about art that I never fully grasped: not in after-school art classes, or college courses, or from the multitude of creative folks I’ve looked up to.
When you’re creating, there is no right and wrong. You can’t be correct or incorrect in your output. Perfectionism has never and will never exist in the world of art.
Perfectionism has always been my blind spot. I’ve loved to draw since I was little, but I never felt like the things I made were satisfactory. The characters I drew, the still lifes I tried to replicate, and the landscapes I attempted to capture never looked enough like the real thing.
My lines were always wonky, my circles disproportional, the perspective slightly off. And this was before the internet, but trust me, younger folk, comparison was a thing then too.
My mom (though she loves to downplay it) is a talented fine artist. My older cousin Genni too. I used to love when she’d come to visit, toting along her sketchbook filled with unicorns. Instead of pulling out my own paper and drawing alongside her, I remember begging her to draw me pictures of Ariel from The Little Mermaid or a My Little Pony character — because she could do them so much better than I could.
Two of my best friends from high school, Francesca and Katie, are also wonderful artists. Even though we each had our individual styles, I couldn’t help but think maybe my work would be better if it looked more like theirs.
My sister Lisa is another artist who comes to mind in the category of people I look up to. Everything she’s ever drawn or painted is a masterpiece in my mind.
Since I could never get things just right, and that drove me crazy, I found the best way around it by becoming a graphic designer.
In graphic design, there are rules, and grids, and an undo button. By using programs like Adobe InDesign, Photoshop, and Illustrator, it was a lot harder to make a mistake, and if you did, you could fix it without anyone knowing.
Sure, I’ve made lots of pretty things as a graphic designer, but I’ve worked so hard to hide from my flaws, my wonky lines and squished circles, and have played things so safe.
Whatever the opposite of failing bravely is, is how I’d describe most of the work I’ve created and shared in adulthood. Succeeding, but like a coward? I think all artists have probably created like a coward at some point, but graphic designers — I have to think we are among the biggest offenders.
So, after 40 years of saying “I’m bad at drawing” and hiding behind the ability to get things exactly right, down to the pixel, I voluntarily sought out something that I knew was going to make me uncomfortable. I signed up for a drawing class.
I knew I needed something low-stakes and which I could work at my own pace, but above all, a program that would make it impossible for me to fall back on my perfectionist tendencies.
Right here on Substack, I found something that looked fun and freeing: A 30-Day Drawing Habit that’s part of a newsletter called
from .It was a challenge that ran in January, and I was joining late, starting in March, but I felt like that made it better. I was already breaking rules.
I was a rebel student in a bunch of other ways too: I also didn’t participate in any of the share threads. I didn’t stick with the directive to draw every single day. Using a ten-minute timer? Get out of here — no, I’m slow, I knew that would never work for me, and the time limit would just make me stressed. Sometimes I took two or three days to complete one lesson.
But the lessons themselves have been exactly what I’ve needed to loosen the hell up. The first few assignments felt more like art therapy where we just got comfortable putting pen or pencil on the page. And almost all of them (so far) have made it impossible to say, “I did this wrong” or “this isn’t good enough.”
Wendy has gotten me doing blind contour drawings (in which you look at your subject matter and don’t look at your page or lift your pen). Nothing feels more unnatural to me, but I did it anyway. Except for one lesson, when she told us to do a contour drawing self-portrait and then write some nice things about ourselves — I’m not there yet, but maybe I’ll circle back to that one.
Exercises that have also forced me to fail bravely:
- Drawing only the negative space
- Drawing upside down
- Drawing with my non-dominant hand
The lessons aren’t finished yet nor has my mindset shifted, based on the fact that I can tell you, in flipping through my little sketchbook, that my favorites are “the pretty ones” instead of the ones that pushed me outside of my comfort zone.
But I’m getting there! I’m learning to shake some of that perfectionism and to let more of me — the real me out.
I was telling a few of the women in my community about this new drawing quest, and one of them asked if I saw it positively affecting my creative work. My answer was 100% yes, and I think it’s only going to get better.
The area where I’m already seeing a difference is my writing, which has been flowing a lot easier. It’s not because I’ve become a better writer, but because I’ve become less self-judgmental of what’s ending up on the page.
When you take away the filters, and all the tools that help you make things perfect, that’s where art gets interesting.
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Coming Soon
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✍️ Creative Exercises/Journal Prompts
What’s something you love to do, but claim to be bad at? Give it another try with the intention of failing bravely.
Sign up for, or conduct your own 30-day creative challenge.
Unleash your inner rebel. Break a rule or two.
☀️ Five good things
When we can recognize the things that bring us the most joy, we invite more of them into our lives. Here are five things that made me happy this week. Share yours below!
Five good things that happened this week:
On Friday night, we went to our local dinner theater to see a production of Oklahoma. One of my favorite things to do during a live performance is to look around the room and see the expressions of everyone watching, which is typically full of joy.
I’m writing this from a coffee shop where I’m enjoying a delicious chicken salad sandwich and an oat milk latte with cinnamon syrup.
I put together an epic '90s-inspired mood board for Steve and my new podcast project. I cannot wait to share more details soon!
We had more friends visiting this week at Disney and enjoyed some special time together, including a yummy dinner at Chefs de France and cocktails on the covered porch outside of Enchanted Rose.
My mom sent me this sweet photo of an Easter display that she and my 7-year-old niece created. They are two of my favorite creative souls, and the idea of them arranging this together just makes my heart soar.
💬 Share your intention
Whether it’s a giant leap, a tiny to-do list item, a habit change, or something else, there is power in accountability, and this is a safe space to share your aim. Some weeks, we’ll fail, others we’ll soar, but with support, we’ll always keep going together.
✨ Question of the week: In what area do you let perfectionism get in your way?
Until next week, get out there and make something beautiful.
Michelle
I'm a fan of the audio component! And I enjoyed this post. It resonated. (Also, I always want to know what everyone is drawing all the time.) I'm happy that drawing is having positive impact on your other creative work.
For the Q of the week: I can't think of one area where perfectionism is NOT getting in my way at the moment. Listening to this post made me acutely aware of it. A rebellious reset is in order, so I'm ditching the tyrannical Friday afternoon to-do list for a nap. Maybe I'll do a blind contour drawing when I wake up.