@Ponyrail Official  
Ah what a good time to get a bit of my creative juices going again.
 
So initially, it was just going to be a generic ballpen,pencil,etc. (Basically any art tool but more likely on the 2 initially mentioned)
 
Then mid-process, I saw Piemation’s “Elements of Cringe” video. Which J then noticed that the CM was the same as what I had in mind.
 
Now, I didn’t want to change the CM drastically, so I got to thinking for a bit & was able to combine a few ideas that came to mind: at that time I drew a variety of things(randomness) and it wasn’t essentially centered around MLP:FiM at the time. So I thought that would be a good addition to the CM.
 
So in the final version (this one), Pen’s CM basically means “drawing at random/being able to draw/create random stuff”.

I wonder why your cutie mark is a pencil with a question mark

@wumbl3  
<3 :,)

uwu