The first thing to consider is what would distinguish each pin from the other. George the donut maker was an Ohio State fan and wore a white Ohio State baseball cap. He always wore white apron and he had a white goatee. Clay, the kayak guy was tall and thin and has a white mustache, baseball cap and sun glasses. The key to personalizing the pins is to identify these and other items that can be part of the whittled pin, and whittle them.
This type of whittling/carving is a form or relief, and is carved from a one dimensional flat cutout. First, determine what you will include in the carving, then make a sketch to scale.
Donut maker: OSU baseball cap, white apron, white goatee.
Kayak renter: Base ball cap, white mustache, and a kayak.
Make a sketch and study it to determine whether the piece can be carved out of one piece of wood or must have parts carved separately. Next, turn your sketch into a pattern by cutting it out, tracing it on to a piece of wood, and scroll sawing the pattern out.
I'll use the kayak rental fellow as an example.
Next I'll do some hat fitting and detail work.
The next posting will complete the pin.