I wear two hats with different names: Madison Woods when I’m wearing the artist hat, Roxann Riedel in real life and real estate. I'm a rock-smashing paint-making artist & a sales agent for Montgomery Whiteley Realty. Hailing from the wild Ozarks in Kingston, Arkansas where my husband and I work toward a sustainable lifestyle.

You can text or call to reach me by either name (see above):
(479)409-3429, or email madison@wildozark.com

Obstacles in my Art Journey | Painting a Portrait

I find it odd that I can paint an animal fairly well, but throw a human into the mix, and if there’s a face, I balk. Human faces are one of the biggest obstacles in my art journey, and I want to scale that mountain. My current painting of my granddaughter and her cow is my challenge. As it stands right now, I’m pleased with what I’ve learned, though there is so soo sooo much more I need to learn. This one will at least be good enough for the gift it was intended to become. And I’m using it as a learning tool for going forward. Hopefully, each time I do another face, it’ll get better.

The Destination

A good painting of a scene that includes humans with faces, in my Ozark oil pigments. Beyond that, there is a series I want to do involving the elements (earth, wind, fire, water, spirit) and human faces. I can’t even begin until I have competency in painting the features of a human face. I also want to begin doing live wedding paintings. I’d like to be able to paint a face, though I could develop a technique of my own that just incorporates blank faces if I want. But I want to have the option, instead of it being my ONLY recourse. I didn’t like having those obstacles in my art journey.

the Obstacles

Why do my attempts to paint this cute kid always look so bad?? Because I can’t paint it correctly. Why can’t I paint it correctly? Because I don’t understand what I’m doing wrong. Except that what I see is not translating into what I’m painting. And I had no idea how to correct the problems, this became like a mountain range of obstacles in my art journey.

First, I needed to understand what I was doing wrong. Then I needed to understand how to do it right. I watched some YouTube tutorials. They made it look so easy to paint a cute kid’s face. I went back to my easel and created another monstrosity. I watched more tutorials, became more and more convinced that maybe, just maybe, I would just not be capable of scaling these mountains.

And then my stubborn nature took over and I kept trying. With each monstrous result, I began to notice small differences in how things looked when I did the wrong thing. I’d wipe off the canvas and start again. Finally, after several attempts, the canvas became unworkable and I set it aside. Perhaps a larger canvas would help. And it did. It allowed me to see in greater details what effects the things I’d done created. So I wiped it off and tried again using a different tactic different from the thing I’d done that didn’t work. I began to learn some things that were helping. I began to feel a glimmer of hope I might actually, eventually, be able to overcome the range of obstacles in my art journey.

I'm learning so much from doing this painting. But at least I've finally managed to make a portrait that looks more human.
This is a huge improvement over previous attempts. See the last section for my self-critique on what’s wrong with it. Even though it’s not perfect, or as good as I’d like it to be, I’m happy with what I’ve learned in this painting. And I’m pleased enough with how it’s turning out to be comfortable giving it to Kady for her gift.

What I Learned | Overcoming the Obstacles in my Art Journey

It’s all about proportions, shading and color. And little things make a huge difference. This shouldn’t be such a surprise, though. It’s the same with animals. Why it took so much anguish to understand how it also applies to humans mystifies me. But that’s what ultimately turned out to be the solution to my problem.

the colors

I thought perhaps my colors were the problem, because they’re handmade and my local colors. They didn’t look natural and lent a monstrous cast to the face. However, this was just an excuse to quit trying. It wasn’t true. I looked up what colors are used to produce skin tones, I saw that I do indeed have the colors I’d need. Ochre yellow, red, russet, brown, and titanium white. And so I had no excuse for why I could not scale at least one of obstacles in my art journey. The supplies weren’t the problem. It wasn’t truly an obstacle. I just thought it was.


Not only do eyes, nose, and mouth need proportional placement, they need to be proportional in size. And faces need to be proportional in size to the body. Hands need to be proportional in size to the arm and everything else has to be in proportion with each other. That’s not to say I can’t deviate from ‘proper’ proportions, but if I do, it’s going to be intentional. I don’t even understand why this was one of the obstacles in my art journey, because it all applies to animals, too. I didn’t get the proportions all right in this painting, but now I can at least see where I unintentionally deviated. So next time, I will pay closer attention.

light and shadow

In this painting, Kady’s crouching position is difficult for me to portray. You know what makes the difference in how a viewer sees it? Shadows and light. Shading. At one point, before I finished her shirt, she appeared to be crouching. Now that her shirt is done, she doesn’t. So I looked back at the photo I took of the stage where it appeared right and compared it to how it looks now. The difference is an area of light on the shirt where it poofs out above her belly. So I’ll fix that soon. The ‘win’ is that I can even SEE that now. The ‘price’ for that win was a week of anguish while I tried to understand why my attempts at painting a human created such monsters.

Shading also affects how old the subject appears. The more definition applied with shadows, the older the subject appears.

Self-Criticism and Critiquing the Art

I am of course always my worst critic. But in this case, I was absolutely justified in being horrified at my results in the beginning. Even though the portrayal isn’t perfect, I don’t expect that. I do expect it to look good enough to make me happy with it, though. I’m not finished with it yet, but I can see some things, like the shirt, that I’d like to improve on before I call it done. There are some things I can’t fix now because it’s too late, like the fact that her face is too wide. And her eyes needed to be lower on her head and smaller. But I am elated that I can at least see the things I need to pay closer attention to next time I attempt a human subject.

All in all, with this painting, I feel as if I have overcome at least this mountain of obstacles in my art journey. Knowing HOW to improve is 9/10 of the solution. And I did gain that knowledge. So I am happy. I’ll post the finished painting here once I’m done. I didn’t post the process of painting this one because it was so bad, I am embarrassed to show you. However, if I can find any of my early photos of the messes I made, I might eventually add them here to show the progress I made. So if you also are trying to overcome this obstacle, you will have hope that it can be done.

One of the Messes

nth Attempt on the first canvas

This was the final attempt on the 5 x 7″ canvas. While she doesn’t look like a monster, at least, and is actually quite cute, in a rough bizarre sort of way, it looks NOTHING like the granddaughter I’m trying to paint. So I put that canvas aside and began a larger one that would allow me to at least attempt better details.

I spent a good week of daily attempts before I finally moved to a larger canvas and put to the test all the things I’d learned in my previous attempts. Seriously, I was at the point of tears and getting depressed. I laugh at myself for that now, but the unwillingness to accept defeat helped me keep trying.



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