I was once asked to draw a pirate fighting an octopus to attach to a job application. 

I'm a pacifist at heart. I also like to push the boundaries of interpretation. And I didn't want to look like every other applicant. 

So I had planned to make my sketch of a Pirate and and Octopus being best friends.

I developed a variety of situations for these characters to be in. These sketches have been slightly reworked to present here, but are good representations of my process.
Selfies are popular, and my favorite sport is bowling...
The caption for these read:
(Left) "Garr, this one's got three left feet, she does!"
(Right) "Scaramouche, Scaramouche, will you do the Fandango?"
A collage of pages from my sketchbook.

And finally, I turned in just an inked version of the following illustration. I didn't get the job, so I've had time to reink and color it since. 
And of course I saved the timelapse from pen to final, which was 25 minutes long before I sped it up...
I felt like a titanic failure when I was told I was too creative for this job. In hindsight, that was a compliment and I'm putting it in my win column.

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