Photographers: How to go beyond the pretty picture?

Like many people in our day and age, I run around with my camera. I think I have decent instincts when it comes to framing, composition, etc. but I find myself developing certain habits. I’ve never taken a photography course but I’m assuming that aside from the technical aspects there must be a part where they push you to articulate why you did something, or why you like a photo and not that photo… something to nudge you to take your work from technically competent to a type of self-expression…

So, if you ever took a photography course, what kind of assignments made you have a kind of breakthrough?

What kind of questions do you find most helpful when reflecting upon your own work? What about in looking at the work of photographers you admire?

If it’s helpful, here’s an example of photos I’ve taken.