This did not go as expected, with people being big fans of their kids, their dad, their potted plant, and so on. Still fair's fair, so I threw them all in a hat and drew them anyway. A year later and I have only finished the first of the four I drew (though I have just started on the second): A German Shepherd.
Unlike most of the things I do that take longer than a few hours, I shared progress on this one as I went along on facebook, so I'll be using those same images here to show the process. For this particular piece I worked 100% in Photoshop.
The first issue I hit was that I didn't have a suitable picture of a German Shepherd to work from. I could probably have found one locally and asked to take a picture, but I had a very specific image in my head, and wanted to find a dog in a similar pose. You would think that a pose such as that above would be every 10th picture of an Alsatian, but you would be wrong. The image I finally found was terribly compressed and 200 pixels high - so about 5% of the size I did the final image. It also didn't have the atmosphere I wanted - being just a dog on a road on a sunny day. Beggars can't be choosers though, so I started on it, and looked up additional reference as I went along, for the details and such.
While quite a few of the references I collected were of snowy roads, the one I ended up referencing the most was one taken from the passenger seat of my wife's car several years ago. Not that it's terribly relevant, just of minor interest.
The trees were very simple to do, with most of the branches just being from a brush I made for a speedpaint early last year. It's quite a versatile brush.
Speaking of brushes, the fur here is predominantly done with a a brush I made a long time ago to simulate streaked brush strokes in specular maps. It's often very useful for hair too, but I found it a little coarse on it's own for the dogs shorter fur.
So I made a new brush specifically for that short hair, called DogFur. It's also quite useful, also being pretty good for close cropped hair on people. Here it's mostly used on the dog's side and legs, but I also used it on the head in the right hand picture, when I did another pass on that.
The last progress image before it was complete. This was just adding shadows, and atmosphere, and making the snow look a little snowier. I felt the image didn't feel cold enough though even though these colours were similar to the photo I was using for reference of the snow, so in the end I tinted it slightly blue. The falling snow was pretty much the last thing I added.
One thing that's not all that clear in these images, it how much things got resized and moved around between the various stages, especially at the beginning, so here's a gif animation of the stages.