What creative process?

I thought a few people (ie my parents) might be interested in seeing some process images from my latest illustration assignment. The prompt was to create a New Yorker cover modeled after the original Eustace Tilley version. Our illustration class generally uses a two-week cycle of creation -- first week is concept sketches and second week is a finished product. For the first week, I submitted two digital sketches (see first two images in the triptych below). There's a lot of thinking behind each of them, but it suffices to say that they are both about bringing the character of Tilley to the digital age.

Unfortunately these ideas were not well received during group crit so I reinvented my idea to focus on Photoshop as a symbol for modern times. In photoshop, things are so quickly changed and their meanings inverted. It becomes a simple but chaotic process as toolbars and windows fill the screen; the process becomes unintelligible to anyone but the artist/manipulator.

What happens if we apply this to personal identity and style of the "hip" twenty-something?If Eustace Tilley is a symbol of the cultured, pensive individual, how would he feel obligated to dress or act today? Is changing one's attitude as simple as changing one's appearance to the outside world? These are the questions I wanted to evoke with my New Yorker cover.

The right-hand image is my first "draft" of the cover/screenshot. Below is my final piece after some revisions for clarity and composition.

Final image is an actual screenshot of a photoshop workspace with several small alterations (blue bar on left, mouse, etc.). I didn't quite accomplish what I was going for with this piece, but this kind of digital method left me pensive and curious to try again.

Hope this was, if not interesting, at least informative!