As with everything, pitfalls await you as you experiment with connotation. For one thing, connotation can be cultural. 9-1-1 instantly brings up painful memories for people in the United States, but this combination of numbers might leave a blank stare on the face of someone who lives in South Africa for instance. Both are English speaking, so they share a language, but that culture did not experience the tragic events of September 11.
What is true culturally is also true individually. Your experiences within your culture differ from your neighbors, your coworker’s, even your own relatives. So what you find meaningful is not what someone else might. Every family has its stories, its inside jokes. These create a micro culture that is specific to that family. “Johnny, do you want a chicken leg?” mades my great aunt bust up laughing, but leaves me cold. She and her brother shared a chicken-leg story from their childhood. They’ve told me it, but I wasn’t there, I don’t remember the mundane story, but the event is etched vividly on Grandpa’s and Great Aunt’s minds such that chicken legs now have additional connotation, but a connotation that cannot be mined to reinforce the emotional scenery of any story I might write.
Another risk is that of purple prose. If you push too hard too fast with heavily laden connotations, you can wind up overwriting your scene such that it becomes melodramatic, trite, or comic. So when I push, I try to get readers to review the words, and then I question them about spots where I felt I might have pushed too hard if they haven’t already mentioned it.
This is a clunker from my past that I took a brief risk with: He finished his run of the line with a feather of hope tickling his liver. The grounds upon which I based this risk were that among the four humors, hope is associated with sanguine, blood, and liver, so I went for the liver tickle. Problem is, the four humors are more remote than, say, liver and onion jokes. And the association of liver with hope is a distant connotation that just doesn’t ring soundly enough with modern readers to rely upon it. Solution? Just drop the last three words. I knew at the time it was likely headed for the axe, but it is worth taking risks. I’ve been amazed at what uncomfortable risks have paid off. Try them, just be prepared to execute them.