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!