This Wisconsin Artist Specializes In Canvas Reproductions Made Just for You

On any given day, Lindsay Sherbondy's easel could hold an energetic abstract awaiting another layer or two, a dreamy landscape or an intricate still life. The through line? How her art makes her feel. Cozy. Happy. Inspired. Those are the emotions she hopes to pass on to anyone who hangs her work in their home. And she's made that part easy: Her Wisconsin-based business, Lindsay Letters, turns original works into customizable canvases with so much visual dimension, you'd swear you feel a brushstroke.

What's the origin story of Lindsay Letters?

I always loved making things. I went to school for graphic design and was hand-lettering my friends' wedding invitations. I always had encouraging Post-it notes around me, so I thought, "What if I could write something encouraging in calligraphy, and people could put it on their walls?" I started, and people asked for more. Pretty soon, they were asking, "Can I have it in burgundy, taupe or a different size?" My background in graphic design made it easy to edit what I was doing. My site was the first website of its kind to offer customizable wall canvases like that.

When did you shift to painting?

I hadn't done much painting since college, but when my daughter was 3, we were out on the porch painting, and we made some abstracts. I was working on my [lettered canvas] Christmas collection at the time and decided to put in some paintings and see how they were received. My first painting I ever offered is called Peppermint Moss; it's one of our bestsellers to this day. So I added more and more.

And more and more styles! What's the most popular now?

Abstract art will never go away, but the top sellers from more recent collections are paintings of a thing.

You led the way by letting people customize their piece. Why was that important to you?

I just didn't want there to be any barriers. Whatever the budget or space or other need there is, I want there to be an option for you. Everybody is worthy of meaningful art. Every piece we sell is custom-printed anyway, every frame is custom-built—so why not make it in whatever size that people need it, whatever frame?

Paintings to the people!

Yes. I remember how I felt when I bought my first piece of art. It was 100-something dollars, a huge investment at the time. I felt really special. I met the artist, and he handed it to me and said, "Congratulations." I wanted to make that feeling and experience accessible to people who might never visit a gallery.

How many paintings do you release each collection?

The core collections have 20 to 30 paintings in them. We put out four big collections each year plus a few pieces intermittently throughout.

That's so much.

Yeah. Painting is the most fun and easiest thing I get to do. I'm so grateful to do it.

What does your process look like?

I don't spend very much time at all painting [versus running the business side]. There are a few weeks a year where I hunker down and am exclusively painting. I can do it with my kids around because it doesn't feel like work. I'll paint a little of the background, make a grilled cheese for a kid, then come back to it. I'll batch paint a bunch of backgrounds, and another layer and another layer and hone each individually. It's helpful for me to have a visual mood board that I reference all the time while creating. I paint 12×16-inch originals because that's the size of our scanner flatbed. So paint, scan, then I lay it out in Photoshop to make sure there are no brush hairs or anything like that. It goes into production from there.

What do you think about while you paint?

I'm creating art to mimic how a space feels. Maybe you can't have a bungalow on the shore, but I'm going to create art that feels like you do. I don't sit down to sketch or paint for me, generally. I never create art without giving it to somebody or making it available on my site. It's like performing a musical: You don't get together to perform it just for you. The part that completes it is the audience. That's how it feels for me. Hopefully, I get to do that for the rest of my life.

This conversation has been edited for length and clarity.