I took this photo of my wife a few months ago when we were in Pittsburgh to watch a live show of My Favorite Murder. It was a rare weekend away for us without kids, and it was very needed.

I met Rachel when she lived in Pittsburgh, and as much as I give her crap about it because I’m a life-long Cleveland sports fan, I know how much the city means to her. So, sitting there, looking at her sip a glass of wine looking out the hotel window at the bridges and cars – it’s a warm memory for me. And this picture is a good exemplar of my wife.

I want to paint this in a large format, and I think I want to be fairly tight with it when I do. Before I go there though, I wanted to sketch it a few times to learn about the value structure, and manipulate the composition a bit.

My first attempt was a quick charcoal sketch on newsprint. I like doing sketches in newsprint because I know it will degrade. Even if I wanted to make something really amazing on Newsprint – it would fall apart pretty quickly because the paper is basically the opposite of archival.

I know that I’m not making any timeless paintings. I want to improve, sure. I want to become an expert one day. I want to master this art form before I die. I want to create lasting art. I want my paintings to hang in museums – and I’m pretty sure any artist who says otherwise is lying.

I want that to happen. But I also want to hit the Powerball Jackpot and become an instant millionaire. The odds of hitting the Powerball are better than the odds of me creating a lasting body of artwork. I know that. I’m under no delusion that I’m a Picasso in the wings.

But, because I want to be, every time I paint I think – maybe I’ll create a masterpiece by accident this time. Of course, it doesn’t happen, but that potential is enough to get my nerves going when I start painting. I think… what if this is the one? What if this is the painting that will become my Starry Night? I indulge in the possibility the same way I daydream about winning the lottery, and I remind myself of reality in that way as well. Regardless, there’s that one in a billion chance that this could become my Starry Night… don’t eff it up. And that right there is enough to make me timid, and afraid. And it shows in every painting.

But when I sketch on Newsprint, I’m literally making garbage. If I accidentally created a masterpiece, it would still be garbage – because Newsprint self destructs. This leaves me free to just go for it. I don’t care if it’s good – or right – because no matter what, I’m practicing.

In this first sketch I moved Rachel to the right a bit so I could give her some room on the left – to open the composition to where she is looking. Unfortunately, the deep dark blacks on the right are what draw me to this image. So, I definitely need to give them plenty of room on the next one.

For this sketch I used a pen. I never sketch with a pen, so this was a fun change for me. I wanted to create the sketch using hatch marks going in only one direction. I tend to draw lines, and then just color them in. But this isn’t what the world is like. Sure, there are places where lines break up the shapes, but not everything is a clear cut shape. By drawing with only diagonal hatch marks, it makes it impossible to draw lines and just color them in, so this was a really good quick exercise in evaluating values on their own. I like the effect I got by doing this – it does help plan for painting because I know where I should plan on the lost edges.

For the next sketch I used hatching going every which way. This took longer than the first version, but it does help plan the composition a little more. I think I like sketching in pen. It forces me to sketch in the same way that I might paint. I have to start at one side and draw to the other (I’m left handed, so it’ll smudge otherwise.) And it goes more quickly than pencil.

Finally, I drew it in large format In charcoal on the Newsprint.

For this sketch I really wanted to focus on accuracy, and getting those darks super dark. I like the composition, but the right side could be darker, and there should not be a cloud coming out of her head. I need to deepen the shadows on the left, I want them as black as her legs. My favorite part is her foot, and her shirt sleeve. The foot was made by just not coloring it in when I colored over that part with deep black charcoal. The sleeve was done by drawing dark lines where the fabric folds were, and that’s all.

I don’t like the hair, I will need to work on that when I paint. It needs to have some soft edges, so I’ll have to experiment with lost and found edges a bit.

The white at her knee, and between her right leg and the curtain are SUPER IMPORTANT.

After this, I tried another version with diagonal hatch marks. This one I cropped to leave out the curtain on the left. I thought it might be superfluous, but looking at this sketch, I think it’s needed.

Next, I’m going to play with the original photo a bit in Photoshop to try some compositional changes. Then I’m going to paint a quick value study to see what areas need more technical experimentation, and I’ll try to come up with some exercises focused on those techniques. For example, I know I’m going to need to have subtle lost and found edges in the hair, which can be a delicate dance. I’ll try to come up with an exercise that’s solely focused on how to create controlled lost and found edges then, experiment with the technique. I also know I need to have very blurry edges in the view through the window juxtaposed with sharp edges on her shirt sleeve in order to exaggerate the depth of field. I’ll need a drill to experiment with that as well. I also need to play with big lost edge washes for where her legs blend with the curtain, and I need to experiment with the folds of the drapes – which I think can be done like Ron Hazell’s method for painting water. I’ll experiment with that as well.

My daughter Winnie also sketched the image. She’s five.. and it’s better than any of mine!