We’re rethinking many of the fundamentals on which our society is based: identity theft, privacy, employment background checks, freedom of speech, and the burden of proof. But the elder statesmen of the high courts aren’t keeping up.

A British MP tasked with mapping out Britain’s digital economy thinks an IP address means “Intellectual Property” address (thanks to @tomcoates for that one). And in a recent case, US Supreme Court Justice John G. Roberts, Jr. asks what the difference is between an email and a pager IS.

How does this affect you? Take ACTA, for example. Haven’t heard of it? That’s because it’s being negotiated in secret, with the help of lobbyists from media companies trying to cling to outmoded revenue streams. Until now, many countries had required that websites comply with “takedown” notices to remove content that infringed on copyrights. ACTA changes this, by imposing a “three strikes” model that gives many governments the ability to disconnect a website if it doesn’t police copyright violations on its own, according to leaked documents obtained by Wired and Wikileaks. This will cripple much of the creativity we see on the web today.

To be blunt: The people making the laws that will change your life don’t understand the technologies you rely on.

The New York Times points out that prevailing telecommunications and privacy laws were written for a dial-up era, and are woefully outdated. Consider that in the early days of the Web, the New Yorker famously said, “on the Internet, nobody knows you’re a dog.” Think for a minute about how inaccurate that is today. Now, everyone knows who we are, because the Internet is how we share things. Laws created for an anonymous web don’t work in a social one. Media, privacy, and free speech all change in a world where content and information sharing is easy.

Plato’s “philosopher kings” brought years of wisdom to their rule, but it’s unlikely any of them would use Facebook today. Legislating the digital world is a catch-22: Those with the wisdom of years lack the technology of youth. Until we reconcile this, we’ll continue to apply real-world laws to online issues.