In modern times, struggling against the orthodoxies of religion, science, and societal norms, people who view things at odd angles compared to other people are deemed to think "outside the box". Said box is a metaphorical representation of said norms and dogmas. This whole metaphor started some years ago--I'm unsure of the etymology.
In more recent times, as entrempreneurs fired up startup after startup (especially since the .com bubble), thinking "outside the box" has shifted a bit from a somewhat backhanded compliment on one's eccentric way of viewing the world and problem solving, to a semi-desirable trait. Those that can do it are viewed either as an enemy of normality and custom, or heralded as a bright mind brimming with new ideas.
The problem I see is that there's a bit of recursion inherent in this model. People are being encouraged, in some circles, to "think outside the box". The only problem with this is that the meaning of the box is changing. Where once thinking outside the box was a sign of intelligence displayed through non-traditional analysis and viewpoints, it is not becoming the new norm. Instead of actually thinking outside the box, as it were, the box has simply expanded to encompass a wider scope of acceptable thought. Less people are thinking outside the box in reality, as the box has simply grown bigger. People are now thinking inside a bigger box.
The key to keeping one's views fresh to not base one's methodologies or thought patterns upon any particular model, be it in an affirmative sense of embracing said norms, or in an antithetical sense of rejecting norms and looking at things soley for the sake of looking at them differently than others do. The engaging intellect will think as it will, regardless of what anyone does or does not accept. One's viewpoints should not be a matter of embracing or rejecting "truths" as other people dictate them; rather, one's viewpoints should always be focused on finding and pursuing one's own truth, no matter where those thoughts lead, or what thought processes are required to get there.
To paraphrase a line from the movie "The Matrix": "Do not try to bend the spoon, for that is impossible. Instead, realise the truth--there is no spoon."
Reject all boxes. The box is a lie, and a pointless distraction on the road to realising the truths about pretty much everything. The intellect is healthiest and the individual best served when unfettered by the bindings with which societal norms would see it shackled. And by transitive properties that I feel link thought and knowledge to spiritual and general happiness, the soul is at its best when allowed to fly freely and find its own way.
