When it Comes to Creative Boundaries, How Hard Should You Push?

The short answer: as hard as it takes for those boundaries to break.
I've said often that if you're not turning someone off, you're not turning someone on. You can't please everyone with creative work. And, in fact, you shouldn't try. If you do, you're producing something lukewarm, something mediocre, something everyone has already seen or heard or felt. Which means something forgettable-and nothing special. Nothing that will make an impact on even a single person. In my opinion, that's the worst fate for any business or product. Not to mention a huge waste of time.
The caveat is that you can't push boundaries just for the sake of pushing them. Shock value has very limited value. It's a cheap and transparent attempt at captivating your audience for a brief moment, and they will immediately recognize it and resent you for it. Instead, every time you push hard at a boundary-whether in a form, subject, or style-it had better be because you're interested in revealing something new, something worth getting people thinking and talking about. Who are some boundary-pushers that you admire? Why?