Sam,
Many thanks for trying the clipboard. I think the image is too small to have all that going on, and it takes away from the simplicity. Let's just work on the chair. You definitely have the general idea, but I'm still trying to get closer to the image on the book cover. Could you try to make the following changes?
1. The chair is facing front
2. The studs are on the rolled arms, not on the back
3. The legs are very straight and the back of the chair is different
4. The light is bouncing off the back of the chair
5. It's a warm brown color. Could you even try to have my name across the chair in white like the book cover?
I know I'm being quite fussy, but I'm really trying to get "the feeling" of the chair.