The author who sells a million copies of her first book, four of the second, wins a prize for the third and dies at the ceremony has had a checkered career: it's got bright spots and dark ones, like a checkerboard.
Checkered is a funny word; it can be used to describe the red and white pattern on a classic tablecloth or the up's and down's of someone's past. You could describe the flag that's waved at a Nascar event as checkered. And if the winning Nascar driver used to work at a car wash, you could say he has had a checkered career.