Making a painting on request

The very talented singer of the band EME, who happens to be my co-worker, asked me if I could make something for her new apartment. And so I did. During the process of making this painting I wanted to make sure that it would come out the way my co-worker envisioned it so I sent her a picture every now and again to keep her up to date. I thought it would be nice to share those pictures here to show the process from beginning to end and to tell what I've learned from the making of this painting. 

The image you see on the right is the inspiration she got for the painting she wanted. She wanted this image, but with her Congolese features and without the hand. Because the apartment where my co-worker lives has a lot of green and pink, she wanted the blue area of the painting to be Emerald green. 

During my break at work, I immediately started sketching in my art journal after I made a picture of her profile. 

I finished the painting and thought it would be cool if her band's name, EME, would appear in the white lines that are on the black area of her headwrap. I couldn't wait to get started at home to make the actual painting! 

But at home it didn't quite work. I had a really hard time getting the face to get the likeness right. After sketching, erasing, sketching, erasing and sketching again, I decided to finish the headwrap first and to fix the face afterwards. 

But the headwrap wasn't easy either. It was difficult for me to find out how large it had to be or what the right angle from the head was. I showed the left picture you see below, to ask my co-worker which lines would be best. She told me the headwrap was too long and too narrow. It had to be more on the top of her head, wider and shorter. On the right picture below you can see the final shape. 

Because the face turned out to be harder then I thought (in my art journal it was easy, because it was so small), I procrastinated a lot. It took a while for me to work on the painting again, but in the meantime I didn't do any other paintings as well. This painting was standing in my way to start any other project, while there was a lot of work to do! 

After a while, my boyfriend helped me to get motivated to finish it, because he saw me struggling with the fact that I couldn't do anything else before that painting was finished and handed over to my colleague. 

So here you see how I eventually painted the face. I'm not completely satisfied, but at that moment, this was the best I could do. I started making the lines on the headwrap with white paint, but this took way too long and I wasn't patient enough to be able to make them neat and tight. So I ended up doing it with a black fineliner as you can see in the picture below. 

Do you notice any other difference between this one and the previous pictures? The ear is covered beneath the headwrap. When I showed her the previous picture, she said the headwrap usually comes over the ear. So I changed it in the end. And added the earring. 

And here it is in her home! 

I didn't do a lot of paintings on request before, but I really found out it's hard for me, cause I am not confident enough about my ability to paint. Therefore I'm too insecure and afraid to fail, that I almost end up doing nothing but procrastinate. 
On the other hand: it's a good way to paint something you normally wouldn't paint and this way you learn new techniques! And you can paint something, without having another canvas you have to make room on your wall for. 

Have you ever made a painting or other piece of art in request? And how did that work for you?