Answer: Pearls of Wisdom is one of my favorites monologues that I've written. Despite the off the wall comedy of it, it's based on a true story of what it is like for some women who grow up in rural Idaho. The most awesome moment was having the monologue performed off Broadway as a part of a night of one acts. Quite an honor.
I would say the key to writing something for off Broadway would be to find something about society that is weird but true. So many things happen around us that don't seem logical or are downright weird. Then create a character in that situation and try to see this oddness from their point of view. I always try to get in the head of my characters and see the world from their point of view, letting their reality (however strange) guide the writing.