For a contest sponsored by the IconFactory.com, I created a set of icons based on my hobby- autocrossing (driving through a course made of cones on a large parking lot). The set of 31 icons was all hand-drawn, starting out either as completely new concepts or occasionally referencing a photo of an object. My style of iconography is to be uniquely representative of an object, yet simplified that it can be deemed "iconic" and also easily recognizable at a small size on a computer screen.
My chiropractor wanted to have a new logo and asked me for some help. He was very open ended on what the design should look like, but wanted to also be able to include the idea of family or children.
I have drawn icons for all of my applications that I build, even if it is a very small utility application. If it is going to be used often, it deserves an icon to be recognizable. I like to start most of my icons in Illustrator in order to get size, spacing, and shape exactly right. After the icon is mostly completed, only then will I use Photoshop to add any final effects, transparency, and shadows.
This was an image I created for myself as an impressionist version of a photo. It was entirely created in Illustrator using the freeform pen tool and gradients. There are no shape blends used.