32 Days of Windmills

My perspective as a designer has often been informed by a love of typography and interest in storytelling. When I first taught myself web design around the impressionable age of 12 or 13, it was to be able to publish my own poetry. (And to make my Neopets store look cool. Let’s be honest.)

It’s been nearly 15 years, nearly six of which were spent sweating the details of print and online publishing for literary and consumer magazines. Storytelling is still an interesting concept to me, but in early 2016 I decided to also seriously focus on design and art direction.

And I wanted to do something to push myself out of my comfort zone, into areas of design I wasn’t very familiar with.


I decided to challenge myself to make a series of daily, themed illustrations. A windmill felt like the perfect form to focus on – it’s simple and rather ordinary, yet iconic.

To focus the project even further, I decided that I would only draw silhouettes of windmills.


Soon enough, I discovered that it’s pretty hard to continue to draw new silhouettes of classic shapes. So I began to make windmills that were increasingly conceptual.


There were also, unfortunately, windmills intended to represent historical forms that quite spectacularly resembled something else. I tried to make four different iterations to prove to myself that I could illustrate a non-offensive version of it. I failed.


After a little over a month, countless Google image searches, and numerous experimental design concepts (not least of which was “What would a Christmas sweater look like as a windmill?”), I decided that it was time to finish the project and move on to other work.

For better or worse, however, “dickmill” will probably always live on in the minds and hearts of my friends.