Here's a bit of my process. I was commissioned to design a jersey logo for the supremely awesome Rocket Ship Park Kickball League, which plays weekly in Valley of the Moon Park.
I started off with three pages of draft designs, playing around with the space themes.
The client wanted the design in red and black with the distinctive rocket ship jungle gym somewhere, with the plan to do the rest of the park in silhouette as well.
When I sat down to do the final design, I wasn't happy with the design and the client wanted it to be printed on a gray athletic shirt. The design wasn't dynamic or fun and it didn't work on gray, so I did a left turn, using some of the themes of the 1st draft, which resulted in something I was really happy with.
As soon as the shirts are available to order, I'll give a shout.