The biggest risk I've ever taken is going on American Idol and trying to be myself. I wasn't going to try too hard to conform, and I knew that it could possibly not work out.
Keep it in tune with the times, but don't write with the specific purpose of trying to create a hit. If you're doing it strictly to make money, you're crazy. There are easier ways to make money.
If you were a medieval scholar reading a book, you knew that there was a reasonable likelihood you'd never see that particular text again, and so a high premium was placed on remembering what you read. You couldn't just pull a book off the shelf to consult it for a quote or an idea.