Painting Mary’s House: Getting It Right the Second Time

Mary, a friend on my block, has lived in her house with her husband for several decades. They were married there and raised their daughter there. I love that they’re still making memories in the same place where so many of them began. After all those years, the house itself is part of the family. That’s what made this painting special to me, and why I wanted to get it right.

She was also my pilot for a 16×20, so we were trying something new together. For a while, I thought it was going really well. Then there was the floating window box.

I’m noticing that when I'm unsure of what I’m doing, I sometimes drift away from the reference photos and start inventing instead of taking the time to look more closely. Sometimes that instinct works, and I like where it takes the painting. This time, I ended up with a box full of flowers and no ledge beneath it, along with a massive, cartoonish tree that worked in its own way but wasn’t what I’d intended.

The flower boxes were clearly important to Mary, which made my floating version especially unfortunate. She was honest about not being able to see past it. I understood, and if I was being honest too, there were other things about the painting I didn’t love. I was attached to the time I’d already put into it, which is a very different thing from being happy with the painting. Still, I really did not want to start over. not just because of time, but because my house portraits are still in their infancy and I'm never really sure what might happen when I start again.

But eventually I did, and I’m so glad. The second version felt much closer to her house, but also to the way I wanted to paint. I could see my skill and style developing as I worked. It’s hard to explain how satisfying that is when you’ve spent a lot of time wondering whether something is working. This time, I could feel it.

One of the most prominent features in the reference photos is the distinctive ivy. It looks almost as if it had been placed intentionally. Mary hadn’t specifically mentioned it, but to me it felt important to the house’s character. The photos also show flowers growing through the ivy on the left side, and I asked how she’d gotten them to do that. I wondered if there was some sort of mounted planter and assumed there was some gardening skill involved.

“Morning glory volunteers,” she told me. “I didn’t plant those. I just couldn’t kill those suckers this year. They kept popping up everywhere, so I let them go.”

Volunteers are plants that sprout on their own from seeds you didn’t deliberately plant. There’s something beautiful to me about flowers growing a little rampant, finding their way into places nobody planned for them. I like the idea that we can stop trying to arrange everything and let some of that happen. I think life works that way too. We put so much care into what we hope it will become, and sometimes something we never planned turns out to be a part we love most.

Mary told me the tree was basically a twig when they bought the house. Now it’s grown so big that it’s needed to be trimmed back. In the painting, its canopy reaches beyond the frame, but the trunk has a presence you can’t ignore. You don’t have to see the whole tree to know that little twig has become something substantial and beautiful. Even as I painted it, it took over and showed me who it was.

The way I painted it happened by accident. Part of my process is drawing in pencil, going over it lightly in ink, and then erasing the pencil. I was trying to hide a stray ink line on the tree, and my pen took over. It started making these thin, scraggly marks that I hadn’t intended, but I liked what they were doing. At first, I tried using them to shade one side of the trunk, but as I kept going, they began to work as a sort of hatching, giving the tree shape and dimension. I leaned into it, and I love how it turned out, particularly close to the reference photo, and totally unintended.

Apparently, sometimes I need to trust the unexpected thing. Other times, I need to put a ledge under it.