One of the ideas that have shaped my thoughts is the existence of loopholes. It seems no matter how carefully we draft an agreement, there's always a loophole.

Part of the reason is the fuzziness of communication. No matter how closely we define a term, there's some fuzziness about it. Some of this is inherent in that fact that we are different people with different life experiences and the roses I have seen in my life are different from the roses you have seen in yours.

Allied to and extending this fuzziness is when new entities like the internet come into existence. Something so different that it changes our basic concepts of how things can be done also challenges the assumptions underlying our agreements.

Then there is human psychology or something in that neighborhood. Not everyone cheats, but certainly many have motivation and desire to. The number and intelligence of the cheaters many times exceeds the number and intelligence of the agreement drafters. If there is a loophole to be found they will find it.

But it was in 1931 that a mathematician proved that loopholes exist in the tightest, most rigorous of our agreements. Fuzzy definitions were no problem because in mathematics the object is the definition. Logic had been formalized in Principia Mathematica so there could be no loopholes in proofs.

Along came Kurt Godel. I'm not going to go into his proof, but it challenged the very roots of mathematics by creating a true statement that couldn't be proved. (I find the ideas fascinating; there are several good explanations of both the proof and its impact on mathematics which you can find with an internet search.)

Godel's Theorem serves for me as a symbol of the much more fuzzy idea I started with; there always seems to be a loophole. Strictly speaking it doesn't say that, but if mathematicians using most rigorous methods can't come up with a complete and consistent system, how can mere mortals or lawyers draft an airtight agreement?

So I don't have much patience with the process of creating ever longer and more verbose documents which seek to eliminate all possibility of cheating. The more verbose, the more opportunities for loopholes. In everything from finance to the tax code to the courts (where hard cases make bad law) we seem to think that just by adding exceptions and overrides we can fix the latest loopholes. All we do is create more opportunities for loopholes.

Simple doesn't answer the needs of a complex world either, but as I have argued elsewhere, leaving some things fuzzy to be decided according to the specifics of an instance, might be a good start.