I agree with Paula F that simply being honest will get a lot of mileage in terms of powerful WDYDWYD images. also, being funny quirky, and sewing yourself into the picture often can give the picture some edge. Not literally of course.
So right, a text that makes you wonder and think... Like the picture of the man on the streets sleeping on his bag, behind him the text written with paint on the wall said "What choice do i have?" That one was a favorite of mine from the moment i saw it...
For me a powerful image that addresses the question of "Why" anything has to have depth of feeling or observation in order to engender the soul of the thing. In other words "Why?" asks for something of a considered and distinctly metaphysical response. For example -- with many of the earlier Three Stooges films -- Moe would go to poke Curly in the eyes with his two fingers, but Curly would hold his hand up sideways and block the shot? Then he'd go "nyuk, nyuk, nyuk...?? Thats a powerful image. It has depth of soul.