Learning to draw better, learning to draw worse
I drew this photo a hundred times, and still I didn't nail it
For weeks I’ve been wanting to draw a photo from thirteen years ago that I found in my desk drawer.

It’s a photo of my three-year-old son hugging me at mile 18 of a marathon. It was the only full marathon I’ve ever run. There are many things I love about the photo, but the main reason I wanted to draw it is that I’ve become fascinated by hands and arms in photographs, fascinated by what we do with them when we’re self conscious and posing, fascinated by how we hold ourselves when we’re candid and awkward or candid and confident.
Hands are hard to draw, but I’m okay with drawing things badly—or at least I thought I was. But then I hit a problem: my three-year-old son’s sweet toddler face.
It bothered me that I couldn’t get it right. I couldn’t get it right in a formal rendering way which is to be expected, but also I couldn’t get it right in a loose, impressionistic way. That bummed me out.
I drew it over and over, and I kept thinking I’d nail it eventually, but I never did.
Instead I thought a lot about drawing and a lot about craft.
1. Skill takes time to develop, and progress isn’t linear.
It’s a hilarious, I guess, that I thought that if I drew the same photo enough times over the course of a few days I’d dramatically improve. My sketches aren’t identical. But they all look like they were sketched by the same person at the same place in her artistic development. Because they were.
2. Skill-building is hard.
When I was in my twenties and first started taking writing seriously, I spent a lot of time deliberately building sentences. It was satisfying but slow and painful work. These days I spend more time worrying over form and structure, but this often happens when I’m walking or doing the dishes. Writing is more playful for me now. Maybe someday I’ll feel inspired to level-up and return to the practice of painstaking sentence-building. But for now, I feel like I’m using muscles I build a long time ago, and mostly I get to have fun.
As I drew, I kept trying to let go of my need to ‘get it right’ or to be ‘good’ at it. I tried to tune into my love for the image. I think this was the right approach, and yet, my left brain kept taking over. Instead of love, I felt frustration. I’d start again, determined to stay with love. 10 seconds in: nope, frustration.

3. It’s good to do hard things.
When I started scanning my sketches for this piece, I had to laugh at myself. I knew I’d drawn the image over and over, but I didn’t realize how many sketches and pages it added up to. I felt satisfaction in the sheer volume of my effort—not unlike running a marathon. I feel a little pride that I have no finished product to show for it. I read somewhere a long time ago that when you hit roadblocks in your creative work, you can take comfort in the fact that you’re actually doing the thing and not just dreaming about doing the thing. And wow—as I typed that out, I started to choke up, so my body agrees.
4. It’s good to do easy things.
All of this felt a little dangerous! Lately, I’ve leaned into drawing as an escape for my busy brain and a new way of being present. This exercise wasn’t that! There were moments where I felt like my new source of joy was slipping away from me. I took small breaks to do fun, low-stakes drawings. Doing so helped me to see that I hadn’t lost access to the joyful work—I had simply taken on a task that was legitimately hard. I couldn’t solve it in a weekend.
I’m taking a break from this image for now, although I’m interested in seeing how my rendering skills progress over time. I might try to draw it (once!) every week or two as a kind of checkpoint.
a prompt
Consider the intersection of play and skill-building in your own work. When does the work feel like play and when does it feel like work? What do you want the balance to feel like?
Comments are open, and I’d love to hear your thoughts!
I really appreciate getting to hear about your creative practice and what it brings up for and within you. A blend of meditation, freedom, and creation.