The hardest part about this challenge is coming up with various iterations. It can be tempting to draw the same thing over and over again with only slight changes. One thing I quickly learned from this first attempt is that I must keep my mind open and to do so, judgement needs to go out the window. Anything goes and (almost) everything is valid. Starting off, I took a very literal approach, but then starting thinking metaphorically, anatomically, and even tried focusing on pure shapes. By the last sketch, my brain felt so fried I even opted to draw the goldfish snack.
Instead of starting off too literal, I wanted to try staying relatively abstract. Having studied architecture for a brief amount of time, I tried channeling my experience of architecture school in the logos. My very first hour of classes was in Design 101, where the class sat in a circle around a plain chair and did a freehand sketch to the best of our abilities. 7 years have passed since that day and I'd like to say that I've gotten at least 7x better since then. Though my architecture lessons were limited to 4 months, they carry on in the way I approach design.