STEP 1: My favorite reference pins
I started by browsing Pinterest in search of pins that I liked. So far this is what I've added to the board (and I'm saying "so far" because I'm sure it will keep growing :))
Once I reviewed the pins that I had added in search of a style guide and recurring themes, I quickly realized that, while I do love 'detailed' in other kinds of artwork, I tend to prefer simplicity when it comes to enamel pins. Most of my chosen pins are quite minimal, with simple typography (if any at all) and very few colors in their designs. Many of them are cute and funny/witty/sarcastic too, and there are recurring themes (cats, skulls, space, coffee). At that point, I more or less knew the direction I wanted to go so it was time to keep moving.
STEP 2: My favorite Apple Metal pin
A quick stop in the way to choose my favorite pin from the Apple Metal website; I've decided to go for this one:
STEP 3: Sketches, sketches!
My first idea was to draw something with a cute Grim Reaper. I did a few sketches pursuing that concept, but none of them quite worked because they lacked something, and no matter how much I tried I couldn't find what it was. It was while drawing aimlessly in one of those frustrated moments, that I started doodling a long cute-looking skull. "Maybe I could add something inside or add a witty pun... wait, this looks a bit like... oooh I think I got it!!"
The skull I had just sketched reminded me slightly of a battery symbol upside down, so I decided to go for a "half-dead battery" concept and make it more literal :D I refined the first sketch, trying out two more variations before actually choosing my fourth sketch as the base to work on (the dead eye was a nice and necessary touch)
STEP 4: My final pin
When working on Illustrator and once I had finished vectorizing my work, I decided to add a final touch by making the top of the skull a bit longer and adding a lighting bolt, because I think the symbol made the concept more solid and added a nice touch.
As you can see, the skull was first a very soft bone color, but in the end I decided to go for pure white. This is the final result, along with a quick mockup I created :)