All our lives we're trained to look at a problem and keep in mind the constraints as we look for a solution.
Given x < 5, for what values of x is x + 4 > 1?
Even in things less objective than math, you're never really pushed when you're young. For example, in English--write a 5 paragraph essay comparing and contrasting the two authors.
No one ever really questions the work, and if they did, they'd get in trouble because it was taken as if they're questioning authority--but let's put ourselves in that position again and pretend like we could ask why. What would you ask?
I'd ask: Why 5 paragraphs--what if I could do it better in 3? What if I wrote a mere sentence--I could make so much more of an impact just because of the accessibility and the stunning terseness. Why even an essay--why not a poem, a meme, a CAD model of a representative piece of architecture?
And now I think, had I done anything but those 5 paragraphs, it would have been not only awkward (what the hell is a CAD file?), I would have been disciplined. Yet, 5 paragraphs in reality sounds like a way less interesting and ineffective way of expressing your thoughts relative to all of the other mediums.
The best entrepreneurs push the boundaries (probably why many of them didn't get along well with school); they drop the constraints, ignore them, forget about them. Look at Stripe, "but it takes time to be able to get a bank to start processing payments online", or FreedomPop, "people need to pay for their data for you to be profitable", or Facebook, "there's already a major social network in Myspace, where's the market for Facebook?", or even Dropbox, "the dropbox founders must be stupid, so many people have tried this yet failed". They don't let constraints dictate what they do; they take criticism, but they don't take shi*--you can't tell them what they can or cannot do.
I actually wrote this today because Carolyn Levy of Y Combinator just created and released Safe
, which is going to change early stage investing for the better and which is a huge move in a constrained industry (the legal side of investing) plagued with "this is how it's always done".