For the past 5 years I have produced a yearly calendar of my landscape photography, and apart from being commercially successful, is also one of my best marketing tools. My experience has shown me a successful calendar needs three things: compelling images, a good design and layout, and a good dosage of marketing.
The first step in making a calendar of course is choosing the images. I try to select from images I’ve made during the past year or so, making sure I’m not repeating any from past calendars. I create a collection for each calendar year in Lightroom, and this makes organization and processing a breeze. Once I select the images, I make virtual copies and place them into the collection (ie. Cal 2012), this way if I crop or otherwise modify them specifically for the calendar, I am not modifying my original RAW files.
I look for images that are appropriate for each month and season, and this seems to create a natural flow and continuity to the calendar that might not exist if the images were chosen at random. Because I also include 12 inspirational quotes, I may choose an image specifically because it adds a strong visual component to a particular quote.