Hi Craig, this is awesome! I am really digging that octopus and your soft painting technique. The character in the bandanna particularly makes me chuckle. I like that he is determined to fight the octopus off with a tiny knife. It shows how determined he is. Some things I would think about that could push this a little further is adding more intense shadows and highlights as well as spreading the colors around. I would think about what items can you push into the background and foreground and add more intense shadows. (Tonally it feels like it sits all on the same level if that makes sense. Try squinting your eyes and see what I mean.) And with the color palette, if you look at it, you will notice all the red is on the right and all the black is on left. Something that could help is highlighting something on the left red so it helps unify the piece as a whole. If you look far away, the Captains hat sort of blends with the sail. What if you made his hat red, or his bird red, or even the sail red? Some ideas to think about.
Overall great work. Keep pursuing your dreams in illustration. I can see you going far with this. The plus side about working a non art job full time is that you are not creatively drained at the end of the day and you can pour all of your creativity and ideas into these illustrations. Keep it up and never stop dreaming. π