Some artists continually seek to tear down boundaries, to find new powder, new territory, new worlds to explore. They're the ones that hop the fence to get to places no one has ever been.
Other artists understand that they need to see the edges of the box if they're going to create work that lasts. No fence, no art.
Can't do both at the same time.
My guess is that you're already one kind of person or the other. When people present you with an opportunity/problem, what's your first reaction? Some people immediately start looking for loopholes or weak boundaries. 'You didn't say we couldn't do xxx'. For these people, the best and most obvious solution is to completely demolish the problem and play by different rules.
Other people, some just as successful, take a hard look at the boundaries and create something that plays within, that follows the rules, but that is likely to win because of this.
In my experience, either can work, but only by someone willing to push harder than most in their push to be remarkable. Going with the flow is a euphemism for failing.