Here's a wordless WaynoVision comic for your amusement.
This cartoonist is always pleased to come up with a gag that's purely visual. Although the idea is as simple as it can be, I of course agonized over the details.
First, I had to decide which of the nautical nonagenarian's legs would be wooden. That was a relatively easy decision—it had to be in the foreground or else it would have been hidden.
Placing the boot on the walker presented more choices. Should it be on the same side as his peg, for balance? Should there be two boots so the walker and the pirate were both fifty percent peg? Should it match the boot he's wearing?
Ultimately, I fell back on some advice I took from one of many nerdly discussions on technique and process that I've had with Bizarro mastermind Dan Piraro. Dan once told me that he assumes the reader's eye usually travels from the upper left corner of a panel to the lower right, the way we in the Western world normally read text. Following that logic, I placed the walker's boot as close to the lower right corner as possible.
I wish I'd remembered that before I produced and discarded so many sketches.