Michael’s post below reminds me of some exquisite, pithy advice I got from a colleague, Gina Nania, about 15 years ago when I was a copy editor at The Charlotte Observer. I can’t recall what process or headline had gone astray, but Gina (not joking, I think) said, "Just pay the fine and never do it again."
Good advice, and it kind of sums up my feeling about experimenting. It’s better to try something and fail than to be dull and safe. Which reminds me of some more simple advice, this from a managing editor many years ago: "Stop boring readers to death."