Here are the steps I took to create the "Circling the Square" TIMESQUARE Watch Body. As I guide you through the steps I followed, I will share plenty of tips and tricks for how you can design your own!
Take advantage of the tools I created for this model kit to help you design faster! Check out this TIMESQUARE Sketch Guide (PDF) that you can use to sketch out your ideas. Or download this TIMESQUARE Dummy (STL) object to import into your modeling tool as a handy reference -- or as a boolean operations tool to punch an electronics cavity into another object you have designed!
Prepare the watch electronics first. Check out Ladyada's Learning System tutorial: TIMESQUARE Watch Kit.
Print a test object from your design software. As a first stage to design, create and export a small file with easy to measure parts on x, y, and z axes. Print this as early in the process as possible and use digital calipers to measure how the physical object compares to the measurement settings in your digital design file.